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Helicene
Chemistry
From Synthesis to Applications
Helicene Chemistry
Chuan-Feng Chen Yun Shen
•

Helicene Chemistry
From Synthesis to Applications

123
Chuan-Feng Chen Yun Shen
Beijing National Laboratory for Molecular Beijing National Laboratory for Molecular
Sciences, CAS Key Laboratory Sciences, CAS Key Laboratory
of Molecular Recognition and Function, of Molecular Recognition and Function,
Institute of Chemistry Institute of Chemistry
Chinese Academy of Sciences Chinese Academy of Sciences
Beijing Beijing
China China

ISBN 978-3-662-53166-2 ISBN 978-3-662-53168-6 (eBook)

DOI 10.1007/978-3-662-53168-6

Library of Congress Control Number: 2016947948

© Springer-Verlag Berlin Heidelberg 2017

This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part
of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations,
recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission
or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar
methodology now known or hereafter developed.
The use of general descriptive names, registered names, trademarks, service marks, etc. in this
publication does not imply, even in the absence of a specific statement, that such names are exempt from
the relevant protective laws and regulations and therefore free for general use.
The publisher, the authors and the editors are safe to assume that the advice and information in this
book are believed to be true and accurate at the date of publication. Neither the publisher nor the
authors or the editors give a warranty, express or implied, with respect to the material contained herein or
for any errors or omissions that may have been made.

Printed on acid-free paper

This Springer imprint is published by Springer Nature

The registered company is Springer-Verlag GmbH Berlin Heidelberg
Preface

Compared with other chiral molecules, helicenes, comprised of ortho-fused

aromatics, bear helicity and p-conjugated structures. Because of the highly con-
torted p-surfaces with superior chiroptical properties, synthetic challenges for the
diversity of the skeletons, interesting interaction behaviors between themselves or
with other (chiral) molecules, the helicene chemistry has been attracting more and
more attention. Since the first report in 1903, it has been developed for more than
110 years. In 1950s, the helical structure was unambiguously demonstrated by
X-ray crystallographic analysis. Moreover, the optical resolution was achieved and
the relationship between the absolute configuration and chiroptical property was
established. Some practical synthetic methods have been discovered, especially in
the last three decades, such as metal-mediated [2+2+2] triynes cycloisomerization,
Diels–Alder addition, and oxidative photocyclization. Some reactions render the
preparation in gram scale, and some reactions could afford helicenes even in
>99 % ee. Due to the advances in preparation, different applications have been
discovered, including environmental-stimulus responsive molecular switches,
asymmetric catalysis, molecular recognition, and organic electronic devices.
Previously, we composed a review, Helicenes: Synthesis and Applications, in
which the structures and properties were briefly introduced, nearly all the synthetic
methods and applications developed before 2012 were summarized. However, since
then, more than 350 peer-reviewed journal papers have been published, but there
are only a few mini-reviews on specific topics among them. This motivated us to
prepare this book Helicene Chemistry: From Synthesis to Applications to describe
the recent progress. Moreover, we hope this book could be a primer for beginners
who plan to enter this research area and also a useful manual for researchers and
graduate students working in this area.
This book is composed of three parts. In Part I, we would like to make an
introduction to helicenes. In Chap. 1, the nomenclature and the historical devel-
opment are introduced. In Chap. 2, the structural features are presented in detail
with crystal structures. The properties are classified by p-conjugated system and the
helicity. The photophysical and electronic behaviors, chiroptical characteristics and

v
vi Preface

racemization process are discussed in different sections. In addition, other properties

and helicenes with charges or open shells are listed at last. In Part II, the practical
synthetic methods are summarized. For the nonselective methods, the widely
accepted ones, such as oxidative photocyclization (Chap. 3), Diels–Alder addition
and Friedel–Crafts-type reactions (Chap. 4), metal-mediated reactions (Chap. 5),
and other methods (Chap. 6) are examined with advantages and disadvantages. The
recent development of asymmetric synthesis is reviewed in Chap. 7 in three cate-
gories: (1) enantioselective approaches, (2) diastereoselective methods, and
(3) strategies based on enantioenriched substrates. The reactivity of helicene
skeletons, the direct C–H functionalization, the useful transformation of functional
groups, and the helicene-based organometallics are discussed in Chap. 8. In Part III,
selected hot research topics in the past 4 years are presented. In Chap. 9, the
helicene-based organocatalysts and helical ligands used in the asymmetric catalysis
are introduced. The chiral recognition, helicene-based sensors, and responsive
switches are summarized in Chap. 10. And the applications of helicenes in bio-
logical realm are presented in Chap. 11. The circularly polarized luminescence and
the organic electronic devices are discussed in Chap. 12. At last, the assembly
behaviors of helicenes at interfaces and in organogels, LB films, and liquid crystals
are reviewed. We sincerely hope the results selected and presented here will attract
more chemists’ attention and advance the development of helicene chemistry.
Finally, we would like to thank June Tang, from Springer for her kind invitation
and help during the preparation of the book. We also thank Han-Xiao Wang and
Wei-Bin Lin from our research group for literature analysis.

Beijing, China Chuan-Feng Chen

Yun Shen
Contents

Part I What Are Helicenes?

1 Introduction to Helicene Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . 3
1.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
1.2 A Historical Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
1.3 Objectives and Literature Coverage . . . . . . . . . . . . . . . . . . . . . . 10
1.4 Books and Reviews on Helicene Chemistry . . . . . . . . . . . . . . . . 11
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
2 Structures and Properties of Helicenes . . . . . . . . . . . . . . . . . . . . . . . 19
2.1 Structural Features . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19
2.2 The p-systems. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
2.3 The Helicity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
2.4 Other Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
2.5 Helicenes with Open Shell and Charges . . . . . . . . . . . . . . . . . . . 34
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36

Part II How to Prepare Helicenes?

3 Oxidative Photocyclization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
4 Diels–Alder and Friedel–Crafts-Type Reactions . . . . . . . . . . . . . . . . 71
4.1 Diels–Alder Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71
4.2 Friedel–Crafts-Type Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . 78
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 84
5 Metal-Mediated Reactions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87
5.1 [2+2+2] Cycloisomerization . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88
5.1.1 Routes a and a′ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88
5.1.2 Route b . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92
5.1.3 Routes c and c′ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93

vii
viii Contents

5.2 Other Metal-Mediated Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 97

5.2.1 Pd-Catalyzed Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 98
5.2.2 Ru-Mediated Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 106
5.2.3 Ti-Mediated Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . 107
5.2.4 Rh-Mediated Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 107
5.2.5 Fe-Mediated Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 109
5.2.6 Au-Mediated Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 111
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 111
6 Other Synthetic Methods . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 117
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 134
7 Asymmetric Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137
7.1 Enantioselective Routes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 139
7.2 Diastereoselective Routes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 144
7.3 Routes Based on Optically Pure Precursors . . . . . . . . . . . . . . . . 148
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 150
8 Reactivity and Transformations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 153
8.1 Transformation of the Helical Skeletons . . . . . . . . . . . . . . . . . . . 154
8.2 Direct C–H Functionalization . . . . . . . . . . . . . . . . . . . . . . . . . . . 157
8.3 Transformation of the Functional Groups . . . . . . . . . . . . . . . . . . 163
8.4 Preparation of Helicene-Embedded Organometallics . . . . . . . . . . 166
8.4.1 Metallocenes with Helicenes . . . . . . . . . . . . . . . . . . . . . 166
8.4.2 Complexes with Helicenic Ligands . . . . . . . . . . . . . . . . 170
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 179

Part III What Are the Applications of Helicenes?

9 Helicenes in Catalysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 187
9.1 Helicenes as Inducers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 188
9.2 Helicene Amide . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 189
9.3 Helicenes with Oxygen Functionalities . . . . . . . . . . . . . . . . . . . . 189
9.4 Helicenes with Nitrogen Functionalities . . . . . . . . . . . . . . . . . . . 189
9.5 Helicenes with Phosphorus Functionalities . . . . . . . . . . . . . . . . . 192
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 198
10 Recognition, Sensors, and Responsive Switches. . . . . . . . . . . . . . . . . 201
10.1 Helicenes for Molecular Recognition . . . . . . . . . . . . . . . . . . . . . 202
10.2 Helicenes as Sensors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 206
10.3 Responsive Switches . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 210
10.3.1 pH-Responsive Switches . . . . . . . . . . . . . . . . . . . . . . . . 210
10.3.2 Redox-Responsive Switches . . . . . . . . . . . . . . . . . . . . . 213
10.3.3 Photo-Responsive Switches . . . . . . . . . . . . . . . . . . . . . . 217
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 218
Contents ix

11 Helicenes in Biochemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 221

References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 227
12 Circularly Polarized Luminescence and Organic Electronics . . . . . . 229
12.1 Circularly Polarized Luminescence . . . . . . . . . . . . . . . . . . . . . . . 229
12.2 Organic Electronics. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 236
12.2.1 Helicenes in OLEDs . . . . . . . . . . . . . . . . . . . . . . . . . . . 236
12.2.2 Helicenes in Transistors . . . . . . . . . . . . . . . . . . . . . . . . . 238
12.2.3 Miscellaneous . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 241
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 244
13 Helicene Assemblies . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 247
13.1 Interfacial Self-Assembly . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 248
13.2 Organogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 254
13.3 Other Assemblies . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 258
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
Appendix: Important Helicene Compounds . . . . . . . . . . . . . . . . . . . . . . . 267
Abbreviations

A Adenine
Ac Acetyl
acac Acetylacetonyl
AFM Atomic force microscopy
AIBN 2,2′-azobis(2-methylpropionitrile)
BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanhroline
BINAP 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl
BINAPO [1,1′-binaphthalene]-2,2′-diylbis(diphenylphosphine oxide)
BINOL 1,1′-bi-2-naphthol
Bmax The maximum brightness
BP Benzophenone
Bphen Bathophenanthroline
CAN Ceric ammonium nitrate
CBP 4,4′-N,N′-dicarbazolebiphenyl
CD Cyclodextrin (only for alpha-CD, beta-CD, gamma-CD)
CD Circular dichroism
CE Cotton effect
CIE Commission Internationale de l′Eclairage
CLSM Confocal laser scanning microscopy
cod 1,5-cyclooctadiene
Cp Cyclopentadienyl
CP Circularly polarized
CPL Circularly polarized luminescence
Cy Cyclohexyl
dba Dibenzylideneacetone
DBU 1,5-diazabicyclo[5,4,0]-5-undecene
DCE 1,2-dichloroethane
DCM Dichrolomethane
DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
DFT Density functional theory

xi
xii Abbreviations

DIPA Diisopropylamine
DMA N,N-dimethylacetamide
DMAP N,N-4-dimethylaminopyridine
DME 1,2-dimethoxyethane
DMF N,N-dimethylformamide
dmso Dimethyl sulfoxide
DNA Deoxyribonucleic acid
DNT 1-methyl-2,4-dinitrobenzene
dppb 1,4-bis(diphenylphosphino)butane
dppf 1,1-bis(diphenylphosphino)ferrocene
dppm 1,1-bis(diphenylphosphino)methane
dppp 1,3-bis(diphenylphosphino)propane
ee Enantiomeric excess
EL Electroluminescence
ENDOR Electron nuclear double resonance
EPR Electron paramagnetic resonance
ESR Electron spin resonance
F8BT Poly[9,9-dioctylfluorene-co-benzothiadiazole]
FVP Flash vacuum pyrolysis
G Guanine
glum Dissymmetric factor
HAT-CN Dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile
HELIXOL 2,2′-dihydroxyhelicene
HELOL 2,2′-bihelicenyl-1,1′-diol
HOMO Highest occupied molecular orbital
HPLC High performance liquid chromatography
ID Drain current
ITO Indium-tin oxide
LAH Lithium aluminum hydride
LB Langmuir–Blodgett
LDA Lithium diisopropylamide
LLC Lyotropic liquid crystalline
LUMO Lowest unoccupied molecular orbital
m-CPBA Meta-chloroperbenzoic acid
MOM Methoxymethyl
MS Molecular sieve
MW Microwave
N/D Not determined
NA Not available
NBS N-bromosuccinimide
NEXAFS Near edge X-ray absorption fine structure
Nf Nonafluorobutanesulfonyl
NIR Near infrared
NIS N-iodosuccinimide
NMP N-methyl-2-pyrrolidinone
Abbreviations xiii

NMR Nuclear magnetic resonance

NP Nanoparticle
NPB 4,4′-bis(1-naphthyl-N-phenylamino)-biphenyl
NR No reaction
NT 1-methyl-4-nitrobenzene
OFET Organic field-effect transistor
OLED Organic light-emitting diode
OPV Organic photovoltaic
OR Optical rotation
PA Picric acid
PAH Polycyclic aromatic hydrocarbon
p-BQ p-benzoquinone
PEDOT Poly(3,4-ethylene dioxylthiophene)
PLED Polymer light-emitting diode
PMMA Polymethylmethacrylate
PPA Polyphosphoric acid
PSS Photostationary state (Chapter 10)
PSS Poly(styrenesulfonate) (Chapter 12)
p-Tol p-tolyl
Py Pyridyl
rt Room temperature
SOMO Singly occupied molecular orbital
STM Scanning tunneling microscope
T Thymine
TAPA 2-(2,4,5,7-tetranitro-9-fluorenylideneaminooxy)propionic acid
TBAF Tetra-N-butylammonium fluoride
TBBD N4,N4,N4′,N4′-tetra([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4,
4′-diamine
TBDMS Tert-butyldimethylsilyl
TCTA Tris(4-(9H-carbazoyl-9-yl)phenyl)amine
Td Decomposition temperature
TEA Triethyl amine
Tf Trifluoromethanesulfonyl
TFA Trifluoroacetic acid
TFAA Trifluoroacetic anhydride
Tg Glass transition temperature
THF Tetrahydrofuran
tht Tetrahydrothiophene
TIPS Triisopropylsilyl
Tm Melting temperature
TMEDA N,N,N′,N′-tetramethylethylenediamine
TMP Lithium 2,2,6,6,-tetramethylpiperidide
TMS Trimethylsilyl
TNT 2-methyl-1,3,5-trinitrobenzene
TPBi 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene
xiv Abbreviations

TS Transition state
Ts p-toluenesulfonyl
UV–vis Ultraviolet–visible
VAZO 1,1′-azobis(cyclohexanecarbonitrile)
Vg Gate voltage
ηc,max The maximum current efficiency
ηp,max The maximum power efficiency
l Carrier mobility
le Electron mobility
lh Hole mobility
 Part I
What Are Helicenes?
Chapter 1
Introduction to Helicene Chemistry

Abstract In this chapter, a brief introduction to helical structure and helicene is

first given followed by the nomenclature. The historical development is discussed
in detail, and some landmarks such as the first reported helicene, the demonstration
of helical structure by X-ray analysis, the first large-scale synthesis by Diels-Alder
addition, and the contributions of leading research groups at different times are
highlighted. This book is aimed to become a primer for beginners who want to enter
this area and also a useful manual for researchers and graduate students. Literatures
from 2012 to early 2016 are covered and important discoveries before 2012 are
emphasized as well. At last, helicene-related books or review articles published
before 2016 are summarized. If readers are interested in a specific topic, more
details could be obtained from them.

Keywords Helicene Helicene chemistry Historical overview Nomenclature

Objectives and literature coverage

1.1 Introduction

Helical structures are very common in our daily life and microscopic world. For
example, at macroscopic level, the beautiful Sunflower Galaxy (Messier 63) pho-
tographed by Hubble Telescope (Fig. 1.1) [1], the violent tornadoes formed by
rotating air, the transitory whirlpools generated by boat paddle, the vines entwined
with trees, at microscopic level, the famous DNA double helix in a cell, the fol-
damers in supramolecular chemistry, they all bear different types of helical forms.
From an energy standpoint, the helical structures stabilize the systems to some
degree.
If benzene rings are added one by one to a benzene molecule at the
ortho-positions as shown in Fig. 1.2, it would be easy to predict that molecules with
more than three rings would cause great steric hindrance. Therefore, the skeletons
spiral up and come into helical shapes to decrease the van der Waals interaction.

© Springer-Verlag Berlin Heidelberg 2017 3

C.-F. Chen and Y. Shen, Helicene Chemistry,
DOI 10.1007/978-3-662-53168-6_1
4 1 Introduction to Helicene Chemistry

Fig. 1.1 The sunflower

galaxy [2]

Fig. 1.2 Structures of

molecules with different
numbers of benzene rings
1 2 3

H H
4 5

Such are helicenes [3–10], one type of polycyclic aromatic compounds with non-
planar screw-shaped structures composed by ortho-fused aromatic rings.
The nomenclature was proposed by Newman and Lednicer in 1956 [3]. For
hexahelicene (Fig. 1.3), “A systematic name is phenanthro[3, 4-c]phenanthrene.
However, a proposal to create the systematic name helicene for nuclei of the
continuously coiled type is at present being considered by American and
International Nomenclature committees. The prefixes, penta, hexa and hepta, etc.,
would be used for five, six and seven, etc., ring compounds.”
This proposal was accepted quickly and widely used in the literatures after
1950s. Another simple method was also accepted: [n]helicene, where n means the
number of aromatics ring in the helical skeleton, and other rings fused to the
backbone should not be counted [4, 6–10]. This method would be adopted in this
1.1 Introduction 5

,
benzo[c]phenanthrene dibenzo[c g]phenanthrene
tetrahelicene pentahelicene
[4]helicene [5]helicene
4 5

phenanthro[3,4-c]phenanthrene benzo[1,2-c:4,3-c']diphenanthrene
hexahelicene heptahelicene
[6]helicene [7]helicene
6 7

Fig. 1.3 Nomenclature of helicenes

book when the name of a helicene is referred to. In addition to the carbohelicenes
that are formed all by benzene rings, if heteroatoms, like O, N, S, P, Si, present on
the backbones (generally named heterohelicenes), they are named oxa-, aza-, thia-,
phospha-, sila[n]helicenes (or silahelicenes), respectively [4–7, 11, 12].
Besides the structures mentioned above, two helicene moieties connected by a
single bond are named bihelicenyls; two helicenes fused together are called double
helicenes; and the helicenes where an aliphatic chain or other fragments that form a
bridge to link the terminal rings are helicenophanes [4, 6, 7, 13, 14].

1.2 A Historical Overview

Although the systematical nomenclature was proposed in 1956, the first two
helicenes (Fig. 1.4), 1,1-dinaphto-2,2-imin 8 and 1,1-dinaphto-2,2-ortho-diazin 9,
could date back to 1903, when Meisenheimer and Witte studied the reduction of
2-nitronaphthalene [15].
Before 1950s, reports on helicene were rare, where the names usually appeared
as dibenzonaphthalene, tribenzonaphthalene, benzophenanthrene, dibenzophenan-
threne, tribenzophenanthrene, etc. [16]. The research mainly focused on the syn-
thetic methods. According to the key step, namely the step to construct helicene
backbone, three strategies were developed, including Pschorr reaction,
Friedel–Crafts acylation, and Diels–Alder addition.
6 1 Introduction to Helicene Chemistry

Fig. 1.4 The first two 11

10
9
helicenes and numbering
12 8
13a
13
13b N8
13c NH N7
1 7
2 13d
3 6
4 5

7-aza[5]helicene 7,8-diaza[5]helicene
8 9

Scheme 1.1 Synthesis of [4] NH2

helicene Diazotation
Pschorr reaction
CO2H
CO2H
11
10
Decarboxylation

Reduction
Dehydration
Oxidation

O O 4
13

Double Friedel-Crafts acylation

HO2C CO2H
12

In 1912, Weitzenböck and Lieb prepared the first carbo[4]helicene from

2-naphthylacetic acid and 2-nitrobenzaldehyde [17]. By condensation and reduc-
tion, diarylethene 10 could be obtained, which was diazotized and treated with
copper powder followed by decarboxylation to give helicene 4 (Scheme 1.1).
Utilizing similar procedure, Weitzenböck and Klingler synthesized the first carbo[5]
helicene 5 in 1918 [18]. Friedel-Crafts acylation was used as well, by which
Newman and Joshel prepared [4]helicene from 3-benzhydrylglutaric acid 12
(Scheme 1.1) [19]. In addition, by virtue of Diels-Alder reaction between
tetrahydro-1,1′-dinaphthyl 14 and maleic anhydride, Clar synthesized [5]helicene 5
via the following route with decarboxylation, reduction, dehydration, and oxidation
(Scheme 1.2) [20]. Based on these synthetic methods, several derivatives of
helicenes had been prepared during these 50 years [21–33].
The next landmark was in 1952, McIntosh et al. for the first time demonstrated
that [5]helicene had a helical structure by X-ray crystallographic analysis, resulted
from the steric hinderance between two terminal rings which prevented the skeleton
1.2 A Historical Overview 7

Scheme 1.2 Synthesis of [5] O

O O O
helicene
15
O

14 16

Oxidation

O
Decarboxylation
Oxidation
O

5 17

Fig. 1.5 Two partially

resolved helicene acids

CO2H

HO2C CO2H
18 19

from assuming a coplanar configuration and had little effect on the benzene ring
structures [34]. This screw-shaped structure rendered the molecule chiral.
Before this, Newman et al. [35] and Bell et al. [36] tested and verified the optical
activity of helicene molecules in 1948 and 1949, respectively. Helicene acid 18
([a]D = +1.4 ± 0.2°, c, 1 in CHCl3) [35] was partially resolved by crystallization of
the diastereomers formed by the reaction with l-menthol (Fig. 1.5); enantioenriched
helicene diacid 19 ([a]D = −47.2°, acetone) [36] was obtained by crystallization of
the morphine salts. Both two groups found that the compounds displayed no optical
activity after several hours at room temperature, which were thermally unstable and
underwent racemization very fast.
The successful resolution of [6]helicene became a milestone achieved by
Newman and co-workers by forming charge transfer complexes in 1955 [37] and
1956 [3]. This strategy opened the door of the chiroptical properties of helicenes. At
this point, people started to know helicenes.
During 1966–1967, Mallory et al. [38], Carruthers [39], Scholz et al. [40], and
Martin et al. [41] independently reported the first examples of helicenes synthesized
by photochemical strategy, namely the oxidative cyclization of diarylethenes
(Scheme 1.3). This greatly accelerated the development of helicene chemistry.
Based on this method, helicenes bearing five to fourteen benzene rings with different
functional groups had been obtained, and the spectral properties including UV,
8 1 Introduction to Helicene Chemistry

Scheme 1.3 Synthesis of [4] hv

helicene [40] and [7]helicene cyclohexane
[41] by photochemical
method 64%
20 4

hv, I2
benzene

66%

21 7

NMR, ORD, CD were systematically studied during the next two decades
[40, 42–44]. Martin group made a great contribution to the exploration of this
strategy [4]; Wynberg group expanded this method to heterohelicenes [11];
Laarhoven group carefully studied the mechanism of the photochemical procedure
[6]. Katz and co-workers improved this method by adding propylene oxide to
promote the effectiveness of the reaction, which became a standard reaction con-
dition afterwards [45].
Another breakthrough was made by Katz and collaborator in 1990, utilizing the
Diels-Alder reaction between the p-benzoquinone and diene to prepare the helicene
quinone in large scale (Scheme 1.4) [46]. It resolved the problem that helicenes
could not be prepared in quantity through photochemical procedures. From then on,
the applications of helicene molecules began to be disclosed.
Compared with planar acenes, helicenes are not only p-conjugated systems, but
also optically active [7, 10]. Therefore, the applications could be classified into two
categories: one is based on the p-conjugated structure, like LB films [47], liquid
crystals [48], optoelectronic material [49], functional polymers [50], and the other one
is related to the helicity, including asymmetric catalysis [51–54], chiral recognition
[55], chiroptical switches [56], nanoscience [57], and biological applications [58].
Meanwhile, the synthetic methods were greatly developed. For example, Starý
and Stará groups developed intramolecular [2+2+2] cycloisomerization of triynes to
construct helicene backbones (Scheme 1.5) [59]. When chiral ligands were used,
asymmetric synthesis could be achieved with high enantioselectivity. Tanaka group
utilized intermolecular [2+2+2] cycloaddition with chiral ligands and realized the

Scheme 1.4 Synthesis of [5] O

helicene bisquinone O

toluene, reflux, 33h O

+ O
17%
O O
22 23 24
2.93 g
1.2 A Historical Overview 9

Scheme 1.5 Synthesis of [7]

helicene by intramolecular [2 Ni(COD)2 (10 mol%)
+2+2] cycloisomerization PPh3 (20 mol%)
THF, RT, 15 min
51%

7
25

enantioselective synthesis of long helicenes (Scheme 1.6) [60, 61]. Carreño and
Urbano groups utilized chiral p-benzoquinone to prepare helicene quinones with
high stereoselectivity (Scheme 1.7) [62]. Crassous, Autschbach, Réau, and col-
leagues had synthesized a variety of organometallic helicenes, which displayed
optimized chiroptical properties (Fig. 1.6) [63].
Helicenes, as a member of polycyclic aromatic hydrocarbons (PAHs) for more
than a century have been attracting more and more attentions to their physical
properties, chemical reactivity, and synthetic challenges. The records of papers
about helicenes are summarized in Fig. 1.7, which was obtained from ISI Web of
Knowledge® website using helicene* as the search term. It is obvious that the
number of publications increased rapidly, especially after 2010. Undoubtedly,

O
O 10 mol% [Rh(cod)2]BF4
(R)-Segphos
CH2Cl2, RT, 1-16 h
O
+ O
O
O PPh2 O
O
O PPh2
27 (P)-(+)-29
28
O 56%, 47% ee
26 (R)-Segphos

Scheme 1.6 Asymmetric synthesis of [9]helicene-like molecule

O Tol
S
O
1) (2 equiv)
31 O O
OEt O EtO
EtO
CH2Cl2, -40 oC, 1 h
2) DDQ, CH2Cl2
CsF, EtI, DMF
-25 oC, 2 d O O rt, 1 h O O
O O
25% (> 99% ee)
82% (> 99% ee)
OEt OEt

(M)-32 (M)-33
OEt
30

Scheme 1.7 Asymmetric synthesis of [7]helicene bisquinone

10 1 Introduction to Helicene Chemistry

Ph Ph +
Ph Ph
P P
Cu
N N

34

Fig. 1.6 Organometallic helicenes

100

80
Record Count

60

40

20

0
1990 1995 2000 2005 2010 2015
Publication Year

Fig. 1.7 Statistics of the literature published from 1990, retrieved on Oct. 21st, 2015

enormous progress has been witnessed in the past 20 years, and this active research
field will get considerable development in the near future.

1.3 Objectives and Literature Coverage

This book is prepared to be a primer for beginners who plan to enter this research
area and also a useful manual for researchers and graduate students working in this
area. Therefore, besides the general physical and chemical properties, we will focus
on the practical synthetic methods as well, which have been widely accepted and
used to prepare helicene in large scale via simple procedures. In addition, the
frontiers of applications will be discussed in detail with regard to the helicity and
the p-conjugated skeletons. The contents is based on the peer-reviewed journal
papers from a thorough search of the literatures published between 2012 and early
2016, and important discoveries before 2012 will also be discussed here to give
readers an overview of the progress of helicene chemistry.
1.4 Books and Reviews on Helicene Chemistry 11

1.4 Books and Reviews on Helicene Chemistry

So far, dozens of book chapters and reviews have been published, and they are
listed in Tables 1.1 and 1.2, respectively. Readers, if interested in a specific area,
could find the related books or review articles to get more information.

Table 1.1 Book chapters on helicenes

Title Author(s) Year Notes Ref.
Polycyclic Hydrocarbons (Vol. I) Clar, E. 1964 [4]-, [5]-, [6]helicenes and their [16]
derivatives prepared before 1964 via
non-photochemical strategies
Photocyclization of Stilbenes and Mallory, 1984 Helicenes prepared by [64]
Related Molecules F. B., photochemical methods before 1980
Mallory,
C. W.
Fascinating Molecules in Organic Vögtle, F. 1992 The properties and synthesis of [65]
Chemistry helicenes
Classics in Hydrocarbon Hopt, H. 2000 The synthesis of helicenes [66]
Chemistry: Syntheses, Concepts,
Perspectives.
Cyclophane Chemistry for 21st Sato, K., 2002 The synthesis of azahelicenes [13]
Century Arai, S.
Cotrimerizations of Acetylenic Agenet, N. 2006 The synthesis of helicenes and [67]
Addition Reactions et al. helicene-like molecules by
metal-mediated [2+2+2] triyne
cycloisomerization
Functional Organic Materials: Rajca, A., 2007 A review of helicenes including the [68]
Syntheses, Strategies, and Miyasaka, synthesis and chiroptical properties
Applications M.
Dynamic Stereochemistry of Wolf, C. 2008 Stereoselective synthesis of [69]
Chiral Compounds: Principles helicenes
and Applications
Strained Hydrocarbons Starý, I., 2009 A brief review of physicochemical [70]
Stará, I. G. properties, synthesis, and the
applications of helicenes
Aromatic Ring Assemblies, Starý, I., 2010 A comprehensive review of [59]
Polycyclic Aromatic Stará, I. G. synthetic methods
Hydrocarbons, and Conjugated
Polyenes
Transition-Metal-Mediated Tanaka, K. 2013 The synthesis of helicenes by [71]
Aromatic Ring Construction metal-mediated reactions, especially
the [2+2+2] cycloaddition
Helical Phosphorus Derivatives: Virieux, 2015 The synthesis of phosphahelicenes [53]
Synthesis and Applications D. et al. and applications in asymmetric
catalysis
Organic Photoredox Chemistry in Gilmore, 2015 The synthesis of helicenes by [72]
Flow K. et al. continuous flow methods
12 1 Introduction to Helicene Chemistry

Table 1.2 Reviews on helicenes

Title Author(s) Journal name, year, Ref.
starting page
Some Observations on the Chemical, Wynberg, H. Acc Chem Res, 1971, [11]
Photochemical, and Spectral Properties of 65
Thiophenes
Helicenes Martin, R. H. Angew Chem Int Ed [4]
Engl, 1974, 649
Chemistry of Heterochemistry Kawazura, H., J Syn Org Chem Jpn, [5]
Yamada, K. 1976, 111
Carbohelicenes and Heterohelicenes Laarhoven, W. Top Curr Chem, 1984, [6]
H., Prinsen, W. 63
J. C.
Helical Molecules in Organic Chemistry Meurer, K. P., Top Curr Chem, 1985, [73]
Vögtle, F. 1
Synthesis and Properties of Helicenes Oremek, G. Chem–Ztg, 1987, 69 [74]
et al.
Carbohelicenes, Heterohelicenes and Related Osuga, H., J Syn Org Chem Jpn, [75]
Systems—Some Aspects of Synthesis and Suzuki, H. 1994, 1020
Reactions
Structure/Chiroptics Relationships of Planar Vögtle, F. et al. Eur J Org Chem, 1998, [76]
Chiral and Helical Molecules 1491
Syntheses of Functionalized and Aggregating Katz, T. J. Angew Chem Int Ed, [77]
Helical Conjugated Molecules 2000, 1921
Recent Developments in the Synthesis of Urbano, A. Angew Chem Int Ed, [78]
Helicene-like Molecules 2003, 3986
Unlocking the Potential of Thiaheterohelicenes: Collins, S. K., Org Biomol Chem, [79]
Chemical Synthesis as the Key Vachon, M. P. 2006, 2518
Photochemical Reactions as Key Steps in Hoffmann, N. Chem Rev, 2008, 1052 [80]
Organic Synthesis
Azahelicenes and Other Similar Tri and Dumitrascu, F. ARKIVOC, 2010, 1 [12]
Tetracyclic Helical Molecules et al.
Photochemical Oxidative Cyclisation of Jørgensen, K. B. Molecules, 2010, 4334 [81]
Stilbenes and Stilbenoids—The
Mallory-Reaction
Advances in the Synthesis of Helicenes Dou, G.-L. Chin J Org Chem, [82]
Shi, D.-Q. 2011, 1989
Helicenes: Synthesis and Applications Shen, Y., Chen, Chem Rev, 2012, 1463 [7]
C.-F.
One Hundred Years of Helicene Chemistry. Part Gingras, M. Chem Soc Rev, 2013, [9]
1: Non-stereoselective Syntheses of 968
Carbohelicenes
One Hundred Years of Helicene Chemistry. Part Gingras, M., Chem Soc Rev, 2013, [10]
2: Stereoselective Syntheses and Chiral et al. 1007
Separations of Carbohelicenes
One Hundred Years of Helicene Chemistry. Part Gingras, M. Chem Soc Rev, 2013, [8]
3: Applications and Properties of 1051
Carbohelicenes
(continued)
References 13

Table 1.2 (continued)

Title Author(s) Journal name, year, Ref.
starting page
Applications of Helical-Chiral Pyridines as Peng, Z., Chem Rec, 2013, 28 [51]
Organocatalysts in Asymmetric Synthesis Takenaka, N.
Metal-Catalyzed Annulation Reactions for Jin, T. et al. Chem Eur J, 2014, [83]
p-Conjugated Polycycles 3554
Helicene-based Transition Metal Complexes: Crassous, Chem Sci, 2014, 3680 [84]
Synthesis, Properties and Applications J. et al.
Cationic Triangulenes and Helicenes: Synthesis, Lacour, J. et al. Chem Soc Rev, 2014, [85]
Chemical Stability, Optical Properties and 2824
Extended Applications of These Unusual Dyes
Helical-Chiral Small Molecules in Asymmetric Narcis, M. J., Eur J Org Chem, 2014, [52]
Catalysis Takenaka, N. 21
Photochemical Reactions Applied to the Hoffmann, N. J Photochem Photobio [86]
Synthesis of Helicenes and Helicene-like C: Photochem Rev,
Compounds 2014, 1
Synthesis, Double-Helix Formation, and Yamaguchi, M. Chem Rec, 2014, 15 [55]
Higher-Assembly Formation of Chiral et al.
Polycyclic Aromatic Compounds: Conceptual
Development of Polyketide Aldol Synthesis
Helicene-like Chiral Auxiliaries in Asymmetric Marinetti, A. Dalton Trans., [54]
Catalysis et al. 2014,15263
Enantioselective Helicene Synthesis by Tanaka, K. et al. Bull Chem Soc Jpn, [61]
Rhodium-Catalyzed [2+2+2] Cycloadditions 2015, 375
Circularly Polarized Luminescence from Simple de la Moya, S. Chem Eur J, 2015, [87]
Organic Molecules et al. 13488
Cyclophanes Containing Large Polycyclic Bodwell, G. Chem Soc Rev, 2015, [14]
Aromatic Hydrocarbons J. et al. 6494
Recent Advances in Stereoselective [2+2+2] Amatore, M., Eur J Org Chem, 2015, [60]
Cycloadditions Aubert, C. 265

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Another random document with
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gorgeous banqueting-hall of her father, she looked and felt as if
assisting at a funeral feast, and that she even then would have been
the better of the visor to prevent many conjectures on what her
saddened looks might mean. But the time for assuming the mask
arrived, and the nobles of the land, with their haughty dames, and
many a knight, and many a damsel fair, bedight in silk and cloth of
gold, and blazing with jewels, graced the tapestried ball-room, on
which a flood of brilliant light was poured from lamp and torch. And
each in joyous mood, cheered by the merry minstrels, and by the
sound of harp and viol, impatiently awaited the commencement of
the dance, when they were informed that it was stayed for an
expected and honourable guest. And now again curiosity was at its
height. But presently there was a flourish of the music, and a cry of
the ushers to make way for the noble Earl of Ormisdale, and the large
doors at the foot of the hall were flung wide open, and the gallant
young earl, masked, and attended by a train of young gentlemen, all
his kinsmen, or picked and chosen friends, advanced amid murmurs
of admiration to the middle of the hall. Here they were met and
welcomed by the baron, who led the earl to his lovely daughter, and
having presented him to her, the guests were presently gratified by
seeing the gallant young nobleman take the hand of the Lady Isabel,
and lead her out to dance. Nor were there any present whose eyes did
not follow them with admiration, though the measure chosen by the
high-born damsel savoured more that night of grace and dignity than
lightness of either heart or heel. Meantime, the old baron was so full
of joy and delight, that it was remarked by all, as he was still seen
near his daughter and her partner. But their hearts were both
quaking: the unhappy Lady Isabel’s with thinking of her promise to
her father, and that of her betrothed with a fear known only to
himself, for he had heard that she had loved, and now observed her
narrowly. And, not content with this, he asked her, as he sat beside
her, many a wily question, till at last he spoke his fears in plain guise,
and she, with many sighs and tears shed within her mask, confessed
the truth; still saying, that for her father’s sake she would be his wife,
if he accepted of her on such terms. But now her father whispered to
her that she must presently prepare to keep her word, as this must be
her bridal-night, for to that purpose alone was this high wassail kept.
Her lover, too, no way daunted by his knowledge of her heart,
pressed on his suit to have it so. And now was the despairing damsel
almost beside herself, when her father, announcing aloud his
purpose to the astonished guests, called for the priest, and caused all
to unmask. But in what words shall we paint the surprise, the
delight, the flood of joy that came upon the heart of the Lady Isabel,
when the earl’s mask was removed, and she beheld in him her much
beloved Roderick, who, his cousin being dead, was now the Earl of
Ormisdale!
And now was each corner of the castle, from basement stone to
turret height, filled with joyous greetings, and the health and
happiness of the noble Earl Roderick, and of his bride, the dutiful
Lady Isabel, deeply drank in many a wassail bowl.
The stately castle and its revels, the proud baron and his pomp, the
beauteous dame and her children’s children, have now passed away
into oblivion, save this slight record, which has only been preserved
in remembrance of the daughter’s virtue, who preferred her father’s
happiness to her own.—Chambers’s Edinburgh Journal, 1833.
 THE DESPERATE DUEL.

By D. M. Moir, M.D.
Nay, never shake thy gory locks at me;
Thou canst not say I did it!—Macbeth.

It was on a fine summer morning, somewhere about four o’clock,

when I waukened from my night’s rest, and was about thinking to
bestir mysel, that I heard the sound of voices in the kail-yard,
stretching south frae our back windows. I listened—and I listened—
and I better listened—and still the sound of the argle-bargling
became more distinct, now in a fleeching way, and now in harsh
angry tones, as if some quarrelsome disagreement had ta’en place. I
hadna the comfort of my wife’s company in this dilemma; she being
awa, three days before, on the top of Tammy Trundle the carrier’s
cart, to Lauder, on a visit to her folks there; her mother (my
gudemother, like) having been for some time ill, with an income in
her leg, which threatened to make a lameter of her in her old age; the
twa doctors there, no speaking of the blacksmith, and sundry skeely
old women, being able to mak naething of the business; so nane
happened to be wi’ me in the room, saving wee Benjie, who was lying
asleep at the back of the bed, with his little Kilmarnock on his head,
as sound as a top. Nevertheless, I lookit for my claes; and opening
one-half of the window-shutter, I saw four young birkies well
dressed; indeed three of them customers of my ain, all belanging to
the toun; twa of them young doctors; ane of them a writer’s clerk;
and the ither a grocer; the hale looking very fierce and fearsome, like
turkey cocks; swaggering about with their hands and arms as if they
had been the king’s dragoons; and priming a pair of pistols, which
ane of the surgeons, a speerity, out-spoken lad, Maister Blister, was
haddin’ in his grip.
I jaloused at ance what they were after, being now a wee up to
firearms; so I saw that skaith was to come o’t, and that I wad be
wanting in my duty on four heads—first, as a Christian; second, as a
man; third, as a subject; and fourth, as a father, if I withheld mysel
frae the scene, nor lifted up my voice, however fruitlessly, against
such crying iniquity as the wanton letting out of human blood; sae
furth I hastened—half-dressed, with my gray stockings rolled up my
thighs, over my corduroys, and my auld hat aboon my cowl—to the
kail-yard of contention.
I was just in the nick of time, and my presence checked the
effusion of blood for a little;—but wait a wee. So high and furious
were at least three of the party, that I saw it was catching water in a
sieve to waste words on them, knowing, as clearly as the sun serves
the world, that interceding would be of no avail. Howsomever, I
made a feint, and threatened to bowl awa for a magistrait, if they
wadna desist, and stop from their barbarous and bluidy purpose;
but, i’fegs, I had better have keepit my counsel till it was asked for.
“Tailor Mansie,” quoth Maister Thomas Blister, with a furious cock
of his eye (he was a queer Eirish birkie, come ower for his
yedication), “since ye have ventured to thrust your nose,” said he,
“where nobody invited ye, you must just stay,” said he, “and abide by
the consequences. This is an affair of honour,” quoth he; “and if ye
venture to stir one foot from the spot, och then,” said he, “by the
poker of St Patrick, but whisk through ye goes one of these leaden
playthings, as sure as ye ever spoiled a coat, or cabbaged broadcloth.
Ye have now come out, ye observe, hark ye,” said ye, “and are art and
part in the business;—and, if one, or both, of the principals be killed,
poor devils,” said he, “we are all alike liable to take our trial before
the Justiciary Court, hark ye; and, by the powers,” said he, “I doubt
not but that, on proper consideration, they will allow us to get off
mercifully, on this side of hanging, by a verdict of manslaughter.”
’Od, I fund mysel immediately in a scrape; but how to get out of it
baffled my gumption. It set me all a shivering; yet I thought that,
come the warst when it wad, they surely wad not hang the faither of a
helpless sma family, that had naething but his needle for their
support, if I made a proper affidavy, about having tried to make
peace between the youths. So, conscience being a brave supporter, I
abode in silence, though not without many queer and qualmish
thochts, and a pit-patting of the heart, no unco pleasant in the
tholing.
“Blood and wounds!” bawled Maister Thomas Blister, “it would be
a disgrace for ever on the honourable profession of physic,” egging
on puir Maister Willie Magneezhy, whose face was as white as
double-bleached linen, “to make any apology for such an insult. You
not fit to doctor a cat,—you not fit to bleed a calf,—you not fit to
poultice a pig,—after three years apprenticeship,” said he, “and a
winter with Doctor Monro? By the cupping-glasses of ’Pocrates,” said
he, “and by the pistol of Gallon, but I would have caned him on the
spot, if he had just let out half as much to me. Look ye, man,” said he,
“look ye, man, he is all shaking” (this was the truth); “he’ll turn tail.
At him like fire, Willie.”
Magneezhy, though sadly frightened, looked a thocht brighter, and
made a kind o’ half stap forrit. “Say that ye’ll ask my pardon once
more,—and if no,” said the puir lad, with a voice broken and
trembling, “then we must just shoot one another.”
“Devil a bit,” answered Mr Bloatsheet, “devil a bit. No, sir; you
must down on your bare knees, and beg ten thousand pardons for
calling me out here, in a raw morning; or I’ll have a shot at you,
whether you will or no.”
“Will you stand that?” said Blister, with eyes like burning coals.
“By the living jingo and the holy poker, Magneezhy, if you stand that
—if you stand that, I say, I stand no longer your second, but leave you
to disgrace, and a caning. If he likes to shoot you like a dog, and not
as a gentleman, then let him do it and be done.”
“No, sir,” replied Magneezhy, with a quivering voice, which he
tried in vain, puir fellow, to render warlike (he had never been in the
volunteers, like me). “Hand us the pistols, then, and let us do or die!”
“Spoken like a hero, and brother of the lancet: as little afraid at the
sight of your own blood, as at that of your patients,” said Blister.
“Hand over the pistols.”
It was an awfu’ business. Gude save us, such goings on in a
Christian land! While Mr Bloatsheet, the young writer, was in the act
of doing what he was bid, I again, but to no purpose, endeavoured to
slip in a word edgeways. Magneezhy was in an awfu’ case; if he had
been already shot, he could not have looked mair clay and corpse-
like; so I took a kind of whispering, while the stramash was drawing
to a bloody conclusion, with Maister Harry Molasses, the fourth in
the spree, who was standing behind Bloatsheet, with a large
mahogany box under his arm, something in shape like that of a
licensed packman, ganging about from house to house through the
country-side, selling toys and trinkets, or niffering plated ear-rings
and sic like, wi’ young lasses, for auld silver coins or cracked tea-
spoons.
“Oh!” answered he, very composedly, as if it had been a canister fu’
of black rappee, or blackguard, that he had just lifted down from his
tap shelf, “it’s just Doctor Blister’s saws, whittles, and big knives, in
case ony of their legs or arms be blawn away, that he may cut them
off.” Little wad have prevented me sinking down through the ground,
had I not remembered, at the preceese moment, that I myself was a
soldier, and liable, when the hour of danger threatened, to be called
out, in marching order, to the field of battle. But by this time the
pistols were handed to the two infatuated young men—Mr
Bloatsheet, as fierce as a hussar dragoon, and Magneezhy, as supple
in the knees as if he was all on oiled hinges; so the next consideration
was to get weel out of the way, the lookers-on running nearly as great
a chance of being shot as the principals, they no being accustomed,
like me, for instance, to the use of arms; on which account, I
scougged mysel behind a big pear-tree; baith being to fire when
Blister gied the word “Off!”
I had hardly jouked into my hidy-hole, when “crack, crack” played
the pistols like lightning, and as soon as I got my cowl ta’en from my
een, and looked about, wae’s me, I saw Magneezhy clap his hand to
his brow, wheel round like a peerie, or a sheep seized wi’ the sturdie,
and then play flap down on his braidside, breaking the necks of half a
dozen cabbage-stocks, three of which were afterwards clean lost, as
we couldna pit them all into the pat at ae time. The hale o’ us ran
forrit, but foremost was Bloatsheet, who, seizing Magneezhy by the
hand, said wi’ a mournful face, “I hope you forgive me?—Only say
this as long as you have breath, for I am off to Leith harbour in half a
minute.”
 The blude was rinning ower puir Magneezhy’s een, and drib-
dribbling frae the neb o’ his nose; so he was truly in a pitiful state;
but he said with more strength than I thocht he could have mustered,
—“Yes, yes, fly for your life, I am dying without much pain—fly for
your life, for I am a gone man!”
Bloatsheet bounced through the bit kail-yard like a maukin, clamb
ower the bit wa’, and aff like mad; while Blister was feeling
Magneezhy’s pulse with ane hand, and looking at his doctor’s watch,
which he had in the ither.
“Do ye think that the puir lad will live, doctor?” said I till him.
He gave his head a wise shake, and only observed, “I dare say, it
will be a hanging business amang us. In what direction do you think,
Mansie, we should all take flight?”
But I answered bravely, “Flee them that will, I’se flee nane. If am
ta’en prisoner, the town-officers maun haul me frae my ain house;
but nevertheless I trust the visibility of my innocence will be as plain
as a pikestaff to the een of the fifteen.”
“What then, Mansie, will we do with poor Magneezhy? Give us
your advice in need.”
“Let us carry him down to my ain bed,” answered I; “I wad not
desert a fellow-creature in his dying hour! Help me down wi’ him,
and then flee the country as fast as you are able!”
We immediately proceeded, and lifted the poor lad, wha had now
dwaumed away, upon our wife’s hand-barrow, Blister taking the feet,
and me the oxters, whereby I got my waistcoat a’ japanned with
blude; so, when we got him laid right, we proceeded to carry him
between us down the close, just as if he had been a stickit sheep, and
in at the back door, which cost us some trouble, being narrow, and
the barrow getting jammed in; but, at lang and last, we got him
streeked out aboon the blankets, having previously shooken Benjie,
and waukened him out of his morning’s nap.
A’ this being accomplished, and got ower, Blister decamped,
leaving me my leeful lane, excepting Benjie, wha was next to
naebody, in the house with the deein’ man. What a frightfu’ face he
had, all smeared ower with blude and pouther! And I really jaloused,
that if he deed in that room, it wad be haunted for ever mair, he
being in a manner a murdered man, so that, even should I be
acquitted of art and part, his ghaist might still come to bother us,
making our house a hell upon yirth, and frightening us out of our
seven senses. But, in the midst of my dreadful surmeeses, when all
was still, so that you might hae heard a pin fall, a knock-knock-knock
cam to the door, on which, recovering my senses, I dreaded first that
it was the death-chap, and syne that the affair had gotten wind, and
that it was the beagles come in search of me; so I kissed little Benjie,
wha was sitting on his creepie, blubbering and greeting for his
parritch, while a tear stood in my ain ee, as I gaed forrit to lift the
sneck, to let the officers, as I thocht, harry our house, by carrying aff
me, its master; but it was—thank Heaven!—only Tammy Bodkin
coming in whistling to his wark with some measuring-papers hinging
round his neck.
“Ah, Tammy,” said I to him, my heart warming at a kent face, and
making the laddie, although my bounden servant by a regular
indenture of five years, a friend in my need, “come in, my man. I fear
ye’ll hae to tak charge of the business for some time to come. Mind
what I tell’d ye about the shaping and the cutting, and no making the
goose ower warm, as I doubt I am about to be harled awa to the
Tolbooth.”
Tammy’s heart louped to his mouth.
“Ay, maister,” he said, “ye’re joking. What should ye have done
that ye should be ta’en to sic an ill place?”
“Ah, Tammy, lad,” answered I, “it is but ower true.”
“Weel, weel,” quo’ Tammy—I really thought it a great deal of the
laddie—“weel, weel, they canna prevent me coming to sew beside ye;
and, if I can tak the measure of customers without, ye can cut the
claith within. But what is’t for, maister?”
“Come in here,” said I to him, “and believe your ain een, Tammy,
my man.”
“Losh me!” cried the puir laddie, glowering at the bluidy face of the
man in the bed. “Ay—ay—ay! maister; save us, maister; ay—ay—ay—
you have na cloured his harnpan wi’ the goose? Ay, maister, maister!
what an unyirthly sight!! I doubt they’ll hang us a’;—you for doing’t,
and me on suspicion, and Benjie as art and part, puir thing. But I’ll
rin for a doctor. Will I, maister?”
 The thocht had never struck me before, being in a sort of a manner
dung stupid; but catching up the word, I said wi’ all my pith and birr,
“Rin, rin, Tammy, rin for life and death!”
Tammy bolted like a nine-year-auld, never looking ahint his tail:
so, in less than ten minutes, he returned, hauling alang auld Doctor
Gripes, whom he had wakened out o’ his bed by the lug and horn, at
the very time I was trying to quiet young Benjie, wha was following
me up and doun the house, as I was pacing to and fro in distraction,
girning and whinging for his breakfast.
“Bad business, bad business; bless us, what is this?” said the auld
doctor, staring at Magneezhy’s bluidy face through his silver
spectacles—“What’s the matter?”
The puir patient knew at once his maister’s tongue, and, lifting up
ane of his eyes—the other being stiff and barkened down—said in a
melancholy voice, “Ah, master, do ye think I’ll get better?”
Doctor Gripes, auld man as he was, started back, as if he had been
a French dancing-master, or had strampit on a het bar of iron. “Tom,
Tom, is this you? What, in the name of wonder, has done this?” Then
feeling his wrist—“But your pulse is quite good. Have you fallen, boy?
Where is the blood coming from?”
“Somewhere about the hairy scaup,” answered Magneezhy, in his
own sort of lingo. “I doubt some artery’s cut through!”
The doctor immediately bade him lie quiet, and hush, as he was
getting a needle and silken thread ready to sew it up; ordering me to
get a basin and water ready, to wash the puir lad’s physog. I did so as
hard as I was able, though I wasna sure about the blude just; auld
Doctor Gripes watching ower my shouther, wi’ a lighted penny
candle in ae hand, and the needle and thread in the ither, to see
where the bluid spouted frae. But we were as daft as wise; so he bade
me tak my big shears, and cut out a’ the hair on the fore part of the
head as bare as my loof; and syne we washed, and better washed; so
Magneezhy got the ither ee up, when the barkened blude was loosed,
looking, though as pale as a clean shirt, mair frighted than hurt; until
it became plain to us all, first to the doctor, syne to me, and syne to
Tammy Bodkin, and last of a’ to Magneezhy himsel, that his skin was
na sae much as peeled; so we helped him out of the bed, and blithe
was I to see the lad standing on the floor, without a haud, on his ain
feet.
I did my best to clean his neckcloth and sark-neck of the blude,
making him look as decentish as possible, considering
circumstances; and lending him, as the Scripture commands, my
tartan mantle to hide the infirmity of his bluidy breeks and
waistcoat. Hame gaed he and his maister thegither, me standing at
our close mouth, wishing them a gude morning, and blithe to see
their backs. Indeed, a condemned thief with the rope about his neck,
and the white cowl tied ower his een, to say naething of his hands
yerked thegither behind his back, and on the nick of being thrown
ower, couldna been mair thankfu’ for a reprieve than I was, at the
same blessed moment. It was like Adam seeing the deil’s rear
marching out o’ Paradise, if ane may be allowed to think sic a thing.
The hale business—tag, rag, and bobtail—soon, however, spunkit
out, and was the town talk for mair than ae day. But ye’ll hear.
At the first I pitied the puir lads, that I thocht had fled for ever and
aye from their native country to Bengal, Seringapatam, Copenhagen,
Botany Bay, or Jamaica; leaving behint them all their friends and
auld Scotland, as they might never hear o’ the gudeness of
Providence in their behalf. But—wait a wee.
Wad ye believe it? As sure’s death, the hale was but a wicked trick
played by that mischievous loon Blister and his cronies, upon ane
that was a simple and saft-headed callant. Deil a haet was in the ae
pistol but a pluff o’ pouther; and, in the ither, a cartridge paper, fu’ o’
bull’s blood, was rammed down upon the charge, the which, hiting
Magneezhy on the ee-bree, had caused a business that seemed to
have put him out o’ life, and nearly put me (though ane of the
volunteers) out of my seven senses.—Mansie Wauch.
 THE VACANT CHAIR.

By John Mackay Wilson.

You have all heard of the Cheviot mountains. They are a rough,
rugged, majestic chain of hills, which a poet might term the Roman
wall of nature; crowned with snow, belted with storms, surrounded
by pastures and fruitful fields, and still dividing the northern portion
of Great Britain from the southern. With their proud summits
piercing the clouds, and their dark, rocky declivities frowning upon
the glens below, thay appear symbolical of the wild and untamable
spirits of the Borderers who once inhabited their sides. We say, you
have all heard of the Cheviots, and know them to be very high hills,
like a huge clasp riveting England and Scotland together; but we are
not aware that you may have heard of Marchlaw, an old, gray-looking
farm-house, substantial as a modern fortress, recently, and, for aught
we know to the contrary, still inhabited by Peter Elliot, the proprietor
of some five hundred surrounding acres. The boundaries of Peter’s
farm, indeed, were defined neither by fields, hedges, nor stone walls.
A wooden stake here, and a stone there, at considerable distances
from each other, were the general landmarks; but neither Peter nor
his neighbours considered a few acres worth quarrelling about; and
their sheep frequently visited each other’s pastures in a friendly way,
harmoniously sharing a family dinner, in the same spirit as their
masters made themselves free at each other’s tables.
Peter was placed in very unpleasant circumstances, owing to the
situation of Marchlaw House, which, unfortunately, was built
immediately across the “ideal line,” dividing the two kingdoms; and
his misfortune was, that, being born within it, he knew not whether
he was an Englishman or a Scotchman. He could trace his ancestral
line no farther back than his great-grandfather, who, it appeared
from the family Bible, had, together with his grandfather and father,
claimed Marchlaw as their birthplace. They, however, were not
involved in the same perplexities as their descendant. The parlour
was distinctly acknowledged to be in Scotland, and two-thirds of the
kitchen were as certainly allowed to be in England;—his three
ancestors were born in the room over the parlour, and, therefore,
were Scotchmen beyond question; but Peter, unluckily, being
brought into the world before the death of his grandfather, his
parents occupied a room immediately over the debatable boundary
line which crossed the kitchen. The room, though scarcely eight feet
square, was evidently situated between the two countries; but, no
one being able to ascertain what portion belonged to each, Peter,
after many arguments and altercations upon the subject, was driven
to the disagreeable alternative of confessing he knew not what
countryman he was. What rendered the confession the more painful
was, that it was Peter’s highest ambition to be thought a Scotsman.
All his arable land lay on the Scottish side; his mother was
collaterally related to the Stuarts; and few families were more
ancient or respectable than the Elliots. Peter’s speech, indeed,
bewrayed him to be a walking partition between the two kingdoms—
a living representation of the Union; for in one word he pronounced
the letter r with the broad, masculine sound of the North Briton, and
in the next with the liquid burr of the Northumbrians.
Peter, or, if you prefer it, Peter Elliot, Esquire of Marchlaw, in the
counties of Northumberland and Roxburgh, was, for many years, the
best runner, leaper, and wrestler between Wooler and Jedburgh.
Whirled from his hand, the ponderous bullet whizzed through the air
like a pigeon on the wing; and the best “putter” on the Borders
quailed from competition. As a feather in his grasp, he seized the
unwieldy hammer, swept it round and round his head,
accompanying with agile limb its evolutions, swiftly as swallows play
around a circle, and hurled it from his hands like a shot from a rifle,
till antagonists shrunk back, and the spectators burst into a shout.
“Well done, squire! the squire for ever!” once exclaimed a servile
observer of titles. “Squire! wha are ye squiring at?” returned Peter.
“Confound ye! where was ye when I was christened squire? My
name’s Peter Elliot—your man, or onybody’s man, at whatever they
like!”
 Peter’s soul was free, bounding, and buoyant as the wind that
carolled in a zephyr, or shouted in a hurricane, upon his native hills;
and his body was thirteen stone of healthy substantial flesh, steeped
in the spirits of life. He had been long married, but marriage had
wrought no change upon him. They who suppose that wedlock
transforms the lark into an owl, offer an insult to the lovely beings
who, brightening our darkest hours with the smiles of affection,
teach us that that only is unbecoming in the husband which is
disgraceful in the man. Nearly twenty years had passed over them;
but Janet was still as kind, and, in his eyes, as beautiful as when,
bestowing on him her hand, she blushed her vows at the altar; and he
was still as happy, as generous, and as free. Nine fair children sat
around their domestic hearth, and one, the youngling of the flock,
smiled upon its mother’s knee. Peter had never known sorrow; he
was blest in his wife, in his children, in his flocks. He had become
richer than his fathers. He was beloved by his neighbours, the tillers
of his ground, and his herdsmen: yea, no man envied his prosperity.
But a blight passed over the harvest of his joys, and gall was rained
into the cup of his felicity.
It was Christmas-day, and a more melancholy-looking sun never
rose on the 25th of December. One vast, sable cloud, like a universal
pall, overspread the heavens. For weeks the ground had been covered
with clear, dazzling snow; and as throughout the day the rain
continued its unwearied and monotonous drizzle, the earth assumed
a character and appearance melancholy and troubled as the heavens.
Like a mastiff that has lost its owner, the wind howled dolefully down
the glens, and was re-echoed from the caves of the mountains, as the
lamentations of a legion of invisible spirits. The frowning, snow-clad
precipices were instinct with motion, as avalanche upon avalanche,
the larger burying the less, crowded downward in their tremendous
journey to the plain. The simple mountain rills had assumed the
majesty of rivers; the broader streams were swollen into the wild
torrent, and, gushing forth as cataracts, in fury and in foam,
enveloped the valleys in an angry flood. But at Marchlaw the fire
blazed blithely; the kitchen groaned beneath the load of preparations
for a joyful feast; and glad faces glided from room to room.
Peter Elliot kept Christmas, not so much because it was Christmas,
as in honour of its being the birthday of Thomas, his first-born, who
that day entered his nineteenth year. With a father’s love, his heart
yearned for all his children; but Thomas was the pride of his eyes.
Cards of apology had not then found their way among our Border
hills; and as all knew that, although Peter admitted no spirits within
his threshold, nor a drunkard at his table, he was, nevertheless, no
niggard in his hospitality, his invitations were accepted without
ceremony. The guests were assembled; and the kitchen being the
only apartment in the building large enough to contain them, the
cloth was spread upon a long, clean, oaken table, stretching from
England into Scotland. On the English end of the board were placed
a ponderous plum-pudding, studded with temptation, and a smoking
sirloin; on Scotland, a savoury and well-seasoned haggis, with a
sheep’shead and trotters; while the intermediate space was filled
with the good things of this life, common to both kingdoms and to
the season.
The guests from the north and from the south were arranged
promiscuously. Every seat was filled—save one. The chair by Peter’s
right hand remained unoccupied. He had raised his hands before his
eyes, and besought a blessing on what was placed before them, and
was preparing to carve for his visitors, when his eyes fell upon the
vacant chair. The knife dropped upon the table. Anxiety flashed
across his countenance, like an arrow from an unseen hand.
“Janet, where is Thomas?” he inquired; “hae nane o’ ye seen him?”
and, without waiting an answer, he continued—“How is it possible he
can be absent at a time like this? And on such a day, too? Excuse me
a minute, friends, till I just step out and see if I can find him. Since
ever I kept this day, as mony o’ ye ken, he has always been at my
right hand, in that very chair; I canna think o’ beginning our dinner
while I see it empty.”
“If the filling of the chair be all,” said a pert young sheep-farmer,
named Johnson, “I will step into it till Master Thomas arrive.”
“Ye’re not a father, young man,” said Peter, and walked out of the
room.
Minute succeeded minute, but Peter returned not. The guests
became hungry, peevish, and gloomy, while an excellent dinner
continued spoiling before them. Mrs Elliot, whose goodnature was
the most prominent feature in her character, strove, by every
possible effort, to beguile the unpleasant impressions she perceived
gathering upon their countenances.
“Peter is just as bad as him,” she remarked, “to hae gane to seek
him when he kenned the dinner wouldna keep. And I’m sure Thomas
kenned it would be ready at one o’clock to a minute. It’s sae
unthinking and unfriendly like to keep folk waiting.” And,
endeavouring to smile upon a beautiful black-haired girl of
seventeen, who sat by her elbow, she continued in an anxious
whisper—“Did ye see naething o’ him, Elizabeth, hinny?”
The maiden blushed deeply; the question evidently gave freedom
to a tear, which had, for some time, been an unwilling prisoner in the
brightest eyes in the room; and the monosyllable, “No,” that
trembled from her lips, was audible only to the ear of the inquirer. In
vain Mrs Elliot despatched one of her children after another, in quest
of their father and brother; they came and went, but brought no
tidings more cheering than the moaning of the hollow wind. Minutes
rolled into hours, yet neither came. She perceived the prouder of her
guests preparing to withdraw, and, observing that “Thomas’s
absence was so singular and unaccountable, and so unlike either him
or his father, she didna ken what apology to make to her friends for
such treatment; but it was needless waiting, and begged they would
use no ceremony, but just begin.”
No second invitation was necessary. Good humour appeared to be
restored, and sirloins, pies, pasties, and moorfowl began to disappear
like the lost son. For a moment, Mrs Elliot apparently partook in the
restoration of cheerfulness; but a low sigh at her elbow again drove
the colour from her rosy cheeks. Her eye wandered to the farther end
of the table, and rested on the unoccupied seat of her husband, and
the vacant chair of her first-born. Her heart fell heavily within her;
all the mother gushed into her bosom; and, rising from the table,
“What in the world can be the meaning o’ this?” said she, as she
hurried, with a troubled countenance, towards the door. Her
husband met her on the threshold.
“Where hae ye been, Peter?” said she, eagerly. “Hae ye seen
naething o’ him?”
“Naething, naething,” replied he; “is he no cast up yet?” And, with
a melancholy glance, his eyes sought an answer in the deserted chair.
His lips quivered, his tongue faltered.
 “Gude forgie me,” said he, “and such a day for even an enemy to be
out in! I’ve been up and doun every way that I can think on, but not a
living creature has seen or heard tell o’ him. Ye’ll excuse me,
neebors,” he added, leaving the house; “I must awa again, for I canna
rest.”
“I ken by mysel, friends,” said Adam Bell, a decent-looking
Northumbrian, “that a faither’s heart is as sensitive as the apple o’
his e’e; and I think we would show a want o’ natural sympathy and
respect for our worthy neighbour, if we didna every one get his foot
into the stirrup without loss o’ time, and assist him in his search. For,
in my rough, country way o’ thinking, it must be something
particularly out o’ the common that would tempt Thomas to be
amissing. Indeed, I needna say tempt, for there could be no
inclination in the way. And our hills,” he concluded, in a lower tone,
“are not ower chancy in other respects, besides the breaking up o’ the
storm.”
“Oh!” said Mrs Elliot, wringing her hands, “I have had the coming
o’ this about me for days and days. My head was growing dizzy with
happiness, but thoughts came stealing upon me like ghosts, and I felt
a lonely soughing about my heart, without being able to tell the
cause; but the cause is come at last! And my dear Thomas—the very
pride and staff o’ my life—is lost—lost to me for ever!”
“I ken, Mrs Elliot,” replied the Northumbrian, “it is an easy matter
to say compose yourself, for them that dinna ken what it is to feel.
But, at the same time, in our plain, country way o’ thinking, we are
always ready to believe the worst. I’ve often heard my father say, and
I’ve as often remarked it myself, that, before anything happens to a
body, there is a something comes ower them, like a cloud before the
face o’ the sun; a sort o’ dumb whispering about the breast from the
other world. And though I trust there is naething o’ the kind in your
case, yet as you observe, when I find myself growing dizzy, as it were,
with happiness, it makes good a saying o’ my mother’s, poor body.
‘Bairns, bairns,’ she used to say, ‘there is ower muckle singing in your
heads to-night; we will have a shower before bedtime.’ And I never,
in my born days, saw it fail.”
At any other period, Mr Bell’s dissertation on presentiments would
have been found a fitting text on which to hang all the dreams,
wraiths, warnings, and marvellous circumstances, that had been
handed down to the company from the days of their grandfathers;
but, in the present instance, they were too much occupied in
consultation regarding the different routes to be taken in their
search.
Twelve horsemen, and some half-dozen pedestrians, were seen
hurrying in divers directions from Marchlaw, as the last faint lights
of a melancholy day were yielding to the heavy darkness which
appeared pressing in solid masses down the sides of the mountains.
The wives and daughters of the party were alone left with the
disconsolate mother, who alternately pressed her weeping children
to her heart, and told them to weep not, for their brother would soon
return; while the tears stole down her own cheeks, and the infant in
her arms wept because its mother wept. Her friends strove with each
other to inspire hope, and poured upon her ear their mingled and
loquacious consolation. But one remained silent. The daughter of
Adam Bell, who sat by Mrs Elliot’s elbow at table, had shrunk into an
obscure corner of the room. Before her face she held a handkerchief
wet with tears. Her bosom throbbed convulsively; and, as
occasionally her broken sighs burst from their prison house, a
significant whisper passed among the younger part of the company.
Mrs Elliot approached her, and taking her hand tenderly within
both of hers—“Oh, hinny! hinny!” said she, “yer sighs gae through my
heart like a knife! An’ what can I do to comfort ye? Come, Elizabeth,
my bonny love, let us hope for the best. Ye see before ye a sorrowin’
mother—a mother that fondly hoped to see you an’—I canna say it—
an’ I am ill qualified to gie comfort, when my own heart is like a
furnace! But, oh! let us try and remember the blessed portion,
‘Whom the Lord loveth He chasteneth,’ an’ inwardly pray for
strength to say ‘His will be done!’”
Time stole on towards midnight, and one by one the unsuccessful
party returned. As foot after foot approached, every breath was held
to listen.
“No, no, no,” cried the mother, again and again, with increasing
anguish, “it’s no the foot o’ my ain bairn;” while her keen gaze still
remained riveted upon the door, and was not withdrawn, nor the
hope of despair relinquished, till the individual entered, and with a
silent and ominous shake of his head, betokened his fruitless efforts.
The clock had struck twelve; all were returned, save the father. The
wind howled more wildly; the rain poured upon the windows in
ceaseless torrents; and the roaring of the mountain rivers gave a
character of deeper ghostliness to their sepulchral silence; for they
sat, each wrapt in forebodings, listening to the storm; and no sounds
were heard, save the groans of the mother, the weeping of her
children, and the bitter and broken sobs of the bereaved maiden,
who leaned her head upon her father’s bosom, refusing to be
comforted.
At length the barking of the farm dog announced footsteps at a
distance. Every ear was raised to listen, every eye turned to the door;
but, before the tread was yet audible to the listeners—“Oh! it is only
Peter’s foot!” said the miserable mother, and, weeping, rose to meet
him.
“Janet, Janet!” he exclaimed, as he entered, and threw his arms
around her neck, “what’s this come upon us at last?”
He cast an inquisitive glance around his dwelling, and a convulsive
shiver passed over his manly frame, as his eye again fell on the
vacant chair, which no one had ventured to occupy. Hour succeeded
hour, but the company separated not; and low, sorrowful whispers
mingled with the lamentations of the parents.
“Neighbours,” said Adam Bell, “the morn is a new day, and we will
wait to see what it may bring forth; but, in the meantime, let us read
a portion o’ the Divine Word, an’ kneel together in prayer, that,
whether or not the day-dawn cause light to shine upon this singular
bereavement, the Sun o’ Righteousness may arise wi’ healing on His
wings, upon the hearts o’ this afflicted family, an’ upon the hearts o’
all present.”
“Amen!” responded Peter, wringing his hands; and his friend,
taking down the “Ha’ Bible,” read the chapter wherein it is written
—“It is better to be in the house of mourning than in the house of
feasting;” and again the portion which saith—“It is well for me that I
have been afflicted, for before I was afflicted I went astray.”
The morning came, but brought no tidings of the lost son. After a
solemn farewell, all the visitants, save Adam Bell and his daughter,
returned every one to their own house; and the disconsolate father,
with his servants, again renewed the search among the hills and
surrounding villages.
 Days, weeks, months, and years rolled on. Time had subdued the
anguish of the parents into a holy calm; but their lost first-born was
not forgotten, although no trace of his fate had been discovered. The
general belief was, that he had perished on the breaking up of the
snow; and the few in whose remembrance he still lived, merely spoke
of his death as a “very extraordinary circumstance,” remarking that
“he was a wild, venturesome sort o’ lad.”
Christmas had succeeded Christmas, and Peter Elliot still kept it in
commemoration of the birthday of him who was not. For the first few
years after the loss of their son, sadness and silence characterized the
party who sat down to dinner at Marchlaw, and still at Peter’s right
hand was placed the vacant chair. But, as the younger branches of
the family advanced in years, the remembrance of their brother
became less poignant. Christmas was, with all around them, a day of
rejoicing, and they began to make merry with their friends; while
their parents partook in their enjoyment, with a smile, half of
approval and half of sorrow.
Twelve years had passed away; Christmas had again come. It was
the counterpart of its fatal predecessor. The hills had not yet cast off
their summer verdure; the sun, although shorn of its heat, had lost
none of its brightness or glory, and looked down upon the earth as
though participating in its gladness; and the clear blue sky was
tranquil as the sea sleeping beneath the moon. Many visitors had
again assembled at Marchlaw. The sons of Mr Elliot, and the young
men of the party, were assembled upon a level green near the house,
amusing themselves with throwing the hammer, and other Border
games, while himself and the elder guests stood by as spectators,
recounting the deeds of their youth. Johnson, the sheep-farmer,
whom we have already mentioned, now a brawny and gigantic fellow
of two-and-thirty, bore away in every game the palm from all
competitors. More than once, as Peter beheld his sons defeated, he
felt the spirit of youth glowing in his veins, and, “Oh!” muttered he,
in bitterness, “had my Thomas been spared to me, he would hae
thrown his heart’s blude after the hammer, before he would hae been
beat by e’er a Johnson in the country!”
While he thus soliloquized, and with difficulty restrained an
impulse to compete with the victor himself, a dark, foreign-looking,
strong-built seaman, unceremoniously approached, and, with his
arms folded, cast a look of contempt upon the boasting conqueror.
Every eye was turned with a scrutinizing glance upon the stranger. In
height he could not exceed five feet nine, but his whole frame was the
model of muscular strength; his features open and manly, but deeply
sunburnt and weather-beaten; his long, glossy, black hair, curled into
ringlets by the breeze and the billow, fell thickly over his temples and
forehead; and whiskers of a similar hue, more conspicuous for size
than elegance, gave a character of fierceness to a countenance
otherwise possessing a striking impress of manly beauty. Without
asking permission, he stepped forward, lifted the hammer, and,
swinging it around his head, hurled it upwards of five yards beyond
Johnson’s most successful throw. “Well done!” shouted the
astonished spectators. The heart of Peter Elliott warmed within him,
and he was hurrying forward to grasp the stranger by the hand, when
the words groaned in his throat, “It was just such a throw as my
Thomas would have made!—my own lost Thomas!” The tears burst
into his eyes, and, without speaking, he turned back, and hurried
towards the house to conceal his emotion.
Successively, at every game, the stranger had defeated all who
ventured to oppose him, when a messenger announced that dinner
waited their arrival. Some of the guests were already seated, others
entering; and, as heretofore, placed beside Mrs Elliot was Elizabeth
Bell, still in the noontide of her beauty; but sorrow had passed over
her features, like a veil before the countenance of an angel. Johnson,
crest-fallen and out of humour at his defeat, seated himself by her
side. In early life he had regarded Thomas Elliot as a rival for her
affections; and, stimulated by the knowledge that Adam Bell would
be able to bestow several thousands upon his daughter for a dowry,
he yet prosecuted his attentions with unabated assiduity, in despite
of the daughter’s aversion and the coldness of her father. Peter had
taken his place at the table; and still by his side, unoccupied and
sacred, appeared the vacant chair, the chair of his first-born,
whereon none had sat since his mysterious death or disappearance.
“Bairns,” said he, “did nane o’ye ask the sailor to come up and tak
a bit o’ dinner wi’ us?”
“We were afraid it might lead to a quarrel with Mr Johnson,”
whispered one of the sons.