Chirality at the Nanoscale

Edited by David B. Amabilino

Further Reading
Carreira, E. M., Kvaerno, L.

Classics in Stereoselective Synthesis

2009 ISBN: 978-3-527-32452-1

Amouri, H., Gruselle, M.

Chirality in Transition Metal Chemistry

Molecules, Supramolecular Assemblies and Materials
2009 ISBN: 978-0-470-06053-7

Ding, K. / Uozumi, Y. (eds.)

Handbook of Asymmetric Heterogeneous Catalysis

2008 ISBN-13: 978-3-527-31913-8

Khler, M., Fritzsche, W.

Nanotechnology
An Introduction to Nanostructuring Techniques
2007 ISBN: 978-3-527-31871-1

Wagnire, G. H.

On Chirality and the Universal Asymmetry

Reections on Image and Mirror Image
2007 ISBN: 978-3-906390-38-3

Samori, P. (ed.)

Scanning Probe Microscopies Beyond Imaging

Manipulation of Molecules and Nanostructures
2006 ISBN: 978-3-527-31269-6

Chirality at the Nanoscale

Nanoparticles, Surfaces, Materials and more

Edited by David B. Amabilino

The Editor Dr. David B. Amabilino Institut de Cincia de Materials de Barcelona (CSIC) Campus Universitari 08193 Bellaterra Spain Graphic designer: Adam

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate. Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliograe; detailed bibliographic data are available on the Internet at http://dnb.d-nb.de. # 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form by photoprinting, microlm, or any other means nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specically marked as such, are not to be considered unprotected by law. Typesetting Thomson Digital, Noida, India Printing betz-druck GmbH, Darmstadt Binding Litges & Dopf GmbH, Heppenheim Printed in the Federal Republic of Germany Printed on acid-free paper ISBN: 978-3-527-32013-4

Contents
Preface XIII List of Contributors XVII List of Abbreviations XXI 1 1.1 1.2 1.2.1 1.2.2 1.3 1.3.1 1.3.2 1.3.3 1.3.4 1.3.5 1.3.6 1.4 1.4.1 1.4.2 1.5 1.5.1 1.5.2 1.6 An Introduction to Chirality at the Nanoscale 1 Laurence D. Barron Historical Introduction to Optical Activity and Chirality 1 Chirality and Life 4 Homochirality 4 Pasteurs Conjecture 7 Symmetry and Chirality 8 Spatial Symmetry 8 Inversion Symmetry: Parity, Time Reversal and Charge Conjugation True and False Chirality 10 Symmetry Violation 14 Symmetry Violation versus Symmetry Breaking 16 Chirality in Two Dimensions 17 Absolute Enantioselection 18 Truly Chiral Inuences 18 Falsely Chiral Inuences 20 Spectroscopic Probes of Chirality in Nanosystems 21 Electronic Optical Activity 22 Vibrational Optical Activity 23 Conclusion 24 References 24 Optically Active Supramolecules 29 Alessandro Scarso and Giuseppe Borsato Introduction to Supramolecular Stereochemistry 29 Survey of Weak Intermolecular Attractive Forces 31 Timescale of Supramolecular Interactions and Racemization Processes 33

2 2.1 2.1.1 2.1.2

Chirality at the Nanoscale: Nanoparticles, Surfaces, Materials and more. Edited by David B. Amabilino Copyright 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-32013-4

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2.2 2.2.1 2.2.1.1 2.2.1.2 2.2.2 2.3 2.3.1 2.3.2 2.4 2.4.1 2.4.1.1 2.4.1.2 2.4.2 2.4.2.1 2.4.2.2 2.5

Self-Assembly of Intrinsically Chiral Molecular Capsules 37 Hydrogen-Bonded Assemblies 37 Double Rosettes 37 Hydrogen-Bonded Capsules 39 Metalligand Assemblies 43 Chiral Induction in the Formation of Supramolecular Systems 46 Chiral Memory Effect in Hydrogen-Bonded Assemblies 46 Chiral Memory Effect in MetalLigand Assemblies 49 Chiral Spaces for Chiral Recognition 51 Enantioselective Recognition within Chiral Racemic Self-Assembled Hosts 52 Hydrogen-Bonded Hosts 52 MetalLigand Hosts 53 Interguests Chiral Sensing within Achiral Self-Assembled Hosts 56 Hydrogen-Bonded Hosts 57 MetalLigand Hosts 60 Conclusion and Outlook 61 References 62 Chiral Nanoparticles 67 Cyrille Gautier and Thomas Brgi Introduction 67 Nanoparticle Properties and Synthesis 68 Nanoparticle Properties 68 Preparation, Purication and Size Separation 71 Preparation 71 Purication and Separation of Nanoparticles 74 Chiroptical Properties of Inorganic Nanoparticles 74 Vibrational Circular Dichroism 74 Circular Dichroism 75 Origin of Optical Activity in Metal-Based Transitions 78 Optically Active Coordination Clusters 80 Nanoparticles of Chiral Organic Compounds 81 Applications 83 Asymmetric Catalysis 83 Nanoparticles in Liquid-Crystal Media 85 Chiral Discrimination 87 Outlook 87 References 87 Gels as a Media for Functional Chiral Nanofibers Sudip Malik, Norifumi Fujita, and Seiji Shinkai A Brief Introduction to Gels 93 Introduction 93 Denition of Gels 94 93

3 3.1 3.2 3.2.1 3.2.2 3.2.2.1 3.2.3 3.3 3.3.1 3.3.2 3.3.3 3.4 3.5 3.6 3.6.1 3.6.2 3.6.3 3.7

4 4.1 4.1.1 4.1.2

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VII

4.1.3 4.1.4 4.2 4.2.1 4.2.2 4.2.3 4.2.4 4.3 4.3.1 4.3.2 4.3.3 4.3.3.1

Classication of Gels 94 Chirality in Gels 95 Chiral Organogels 96 Steroid-Based Chiral Gelators 96 Pyrene-Based Chiral Gelators 103 Diaminoyclohexane-Based Chiral Gelators 103 OPV-Based Chiral Gelators 105 Chiral Hydrogels 108 Chiral Fatty Acids 108 Chiral Sugar-Based Gelators 109 Miscellaneous Chiral Hydrogelators 110 The Future of Chiral Gels in Nanoscience and Nanotechnology References 111

111

5 5.1 5.2 5.2.1 5.2.1.1 5.2.1.2 5.2.1.3 5.2.2 5.2.2.1 5.2.2.2 5.2.2.3 5.2.3 5.2.3.1 5.2.3.2 5.2.3.3 5.3 5.3.1 5.3.1.1 5.3.1.2 5.3.1.3 5.3.2 5.3.3 5.3.4 5.3.4.1 5.3.4.2 5.4 5.4.1 5.4.1.1

Expression of Chirality in Polymers 115 Teresa Sierra Historical Perspective on Chiral Polymers 115 Chiral Architecture Control in Polymer Synthesis 117 Polymerization of Chiral Assemblies 117 Chiral Organization Through H-Bonding Interactions 118 Chiral Organization Through p-Stacking Interactions 120 Chiral Organization Through Mesogenic Driving Forces 121 Control of Chiral Architecture During Polymerization 123 Polymerization in Chiral Solvents 123 Polymerization with Chiral Templates 127 Polymerization of Chiral Assemblies by Circularly Polarized Radiation 128 Chiral Architecture Control upon Polymerization: Noncovalent Interactions 129 Control of the Chiral Architecture by H-Bonding Interactions 129 Control of the Chiral Architecture by p-Stacking and Steric Factors 133 Chiral Superstructures by p-Interactions: Chiral Aggregates 134 Asymmetry Induction in Nonchiral Polymers 137 Induction Through Noncovalent Interaction with Chiral Molecules 137 Chiral Induction by AcidBase Interactions 137 Chiral Induction by HostCation Interactions 143 Chiral Induction by Metal Coordination 143 Induction Through Noncovalent Interaction with Chiral Polymers 146 Induction Through the Formation of Inclusion Complexes 147 Induction by a Chiral External Stimulus 150 Solvent-Induced Chirality 150 Light-Induced Chirality 151 Chiral Memory Effects. Tuning Helicity 154 Memory Effects from Chiral Polymers 154 Temperature- and/or Solvent-Driven Memory Effects 154

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5.4.1.2 5.4.2 5.5 5.5.1 5.5.2 5.5.3 5.6 5.6.1 5.6.1.1 5.6.1.2 5.6.2 5.6.3 5.6.4 5.6.4.1 5.6.4.2 5.6.4.3 5.6.4.4 5.7

Light-Driven Memory Effects 157 Memory Effects from Achiral Polymers 158 Chiral Block-Copolymers and Nanoscale Segregation 161 Chiral Block-Copolymers: Nanoscale Segregation in the Bulk 162 Chiral Block-Copolymers: Nanoscale Segregation in the Mesophase 162 Chiral Block-Copolymers: Nanoscale Segregation in Solvents. Amphiphilic Block-Copolymers 165 Templates for Chiral Objects 169 Templates for Chiral Supramolecular Aggregates 169 Templating with Natural Helical Polymers 169 Templating with Synthetic Helical Polymers 172 Molecular Imprinting with Helical Polymers 174 Templating by Wrapping with Helical Polymers 175 Alignment of Functional Groups 176 Polyisocyanides 176 Polypeptides 178 Polyacetylenes 178 Foldamers 179 Outlook 180 References 181 Nanoscale Exploration of Molecular and Supramolecular Chirality at Metal Surfaces under Ultrahigh-Vacuum Conditions 191 Rasmita Raval Introduction 191 The Creation of Surface Chirality in 1D Superstructures 192 The Creation of 2D Surface Chirality 196 2D Supramolecular Chiral Clusters at Surfaces 196 2D Covalent Chiral Clusters at Surfaces 199 Large Macroscopic 2-D Chiral Arrays 200 Chiral Nanocavity Arrays 204 Chiral Recognition Mapped at the Single-Molecule Level 205 Homochiral Self-Recognition 205 Diastereomeric Chiral Recognition 207 Diastereomeric Chiral Recognition by Homochiral Structures 207 Diastereomeric Chiral Recognition by Heterochiral Structures 209 Summary 211 References 212 Expression of Chirality in Physisorbed Monolayers Observed by Scanning Tunneling Microscopy 215 Steven De Feyter, Patrizia Iavicoli, and Hong Xu Introduction 215 How to Recognize Chirality at the Liquid/Solid Interface 217 Chirality at the Level of the Monolayer Symmetry 217

6.1 6.2 6.3 6.3.1 6.3.2 6.3.3 6.3.4 6.4 6.4.1 6.4.2 6.4.2.1 6.4.2.2 6.5

7.1 7.2 7.2.1

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7.2.2 7.2.3 7.3 7.4 7.5 7.6 7.6.1 7.6.2 7.7 7.8 7.9

Chirality at the Level of the Monolayer Substrate Orientation 219 Determination Absolute Conguration 220 Chirality in Monolayers Composed of Enantiopure Molecules 221 Polymorphism 228 Is Chirality Always Expressed? 230 Racemic Mixtures: Spontaneous Resolution? 231 Chiral Molecules 231 Achiral Molecules 234 Multicomponent Structures 237 Physical Fields 240 Outlook 240 References 243 Structure and Function of Chiral Architectures of Amphiphilic Molecules at the Air/Water Interface 247 Isabelle Weissbuch, Leslie Leiserowitz, and Meir Lahav An introduction to Chiral Monolayers on Water Surface 247 Two-Dimensional Crystalline Self-Assembly of Enantiopure and Racemates of Amphiphiles at the Air/Water Interface; Spontaneous Segregation of Racemates into Enantiomorphous 2D Domains 248 Langmuir Monolayers of Amphiphilic a-Amino Acids 249 Domain Morphology and Energy Calculations in Monolayers of N-acyl-a-Amino Acids 253 Stochastic Asymmetric Transformations in Two Dimensions at the Water Surface 254 Self-Assembly of Diastereoisomeric Films at the Air/Water Interface 255 Interactions of the Polar Head Groups with the Molecules of the Aqueous Environment 256 Interdigitated Bi- or Multilayer Films on the Water Surface 261 Structural Transfer from 2D Monolayers to 3D Crystals 263 Homochiral Peptides from Racemic Amphiphilic Monomers at the Air/Water Interface 265 Conclusions 268 References 268 Nanoscale Stereochemistry in Liquid Crystals 271 Carsten Tschierske The Liquid-Crystalline State 271 Chirality in Liquid Crystals Based on Fixed Molecular Chirality Chiral Nematic Phases and Blue Phases 274 Chirality in Smectic Phases 276 Polar Order and Switching in Chiral LC Phases 276 Ferroelectric and Antiferroelectric Switching 276 Electroclinic Effect 279

8.1 8.2

8.3 8.3.1 8.4 8.5 8.6 8.7 8.8 8.9 8.10

9 9.1 9.2 9.2.1 9.2.2 9.2.3 9.2.3.1 9.2.3.2

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Contents

9.2.3.3 9.2.4 9.2.5 9.2.6 9.3 9.3.1 9.3.2 9.4 9.4.1 9.4.2 9.4.3 9.4.4 9.4.4.1 9.4.4.2 9.5 9.5.1 9.5.2 9.5.3 9.5.4 9.5.5 9.6 9.7

Electric-Field-Driven Deracemization 279 Chirality Transfer via GuestHost Interactions 279 Induction of Phase Chirality by External Chiral Stimuli 281 Chirality in Columnar LC Phases 282 Chirality Due to Molecular Self-Assembly of Achiral Molecules 284 Helix Formation in Columnar Phases 284 Helical Filaments in Lamellar Mesophases 287 Polar Order and Chirality in LC Phases Formed by Achiral Bent-Core Molecules 288 Phase Structures and Polar Order 288 Superstructural Chirality and Diastereomerism 290 Switching of Superstructural Chirality 291 Macroscopic Chirality and Spontaneous Reection Symmetry Breaking in Banana Phases 292 Layer Chirality 292 Dark Conglomerate Phases 292 Spontaneous Reection-Symmetry Breaking in Other LC Phases 295 Chirality in Nematic Phases of Achiral Bent-Core Molecules 295 Spontaneous Resolution of Racemates in LC Phases of Rod-Like Mesogens 295 Deracemization of Fluxional Conformers via Diastereomeric Interactions 296 Chirality in Nematic, Smectic and Cubic Phases of Achiral Rod-Like Molecules 296 Segregation of Chiral Conformers in Fluids, Fact or Fiction? 296 Liquid Crystals as Chiral Templates 298 Perspective 299 References 299 The Nanoscale Aspects of Chirality in Crystal Growth: Structure and Heterogeneous Equilibria 305 Grard Coquerel and David B. Amabilino An introduction to Crystal Symmetry and Growth for Chiral Systems. Messages for Nanoscience 305 Supramolecular Interactions in Crystals 308 Hydrogen Bonds 309 Interaromatic Interactions 310 Electrostatic Interactions 311 Modulation of Noncovalent Interactions with Solvent 312 Polymorphism 312 Symmetry Breaking in Crystal Formation 312 Spontaneous Resolution of Chiral Compounds 313 Spontaneous Resolution of Achiral Compounds 315 Resolutions of Organic Compounds 317

10

10.1 10.2 10.2.1 10.2.2 10.2.3 10.2.4 10.2.5 10.3 10.3.1 10.3.2 10.4

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10.5 10.6 10.6.1 10.6.2 10.7 10.7.1 10.7.2 10.8 10.9

Resolutions of Coordination Compounds with Chiral Counterions 320 Thermodynamic Considerations in the Formation of Chiral Crystals 322 What is the Order of a System Composed of Two Enantiomers? Resolution by Diastereomeric Associations 331 Inuencing the Crystallization of Enantiomers 335 Solvent 335 Preferential Nucleation and Inhibition 336 Chiral HostGuest Complexes 338 Perspectives 341 References 341

322

11

11.1 11.2 11.3 11.4 11.5 11.6 11.7 11.8 11.9 11.10 11.11 11.12 11.13

Switching at the Nanoscale: Chiroptical Molecular Switches and Motors 349 Wesley R. Browne, Dirk Pijper, Michael M. Pollard, and Ben L. Feringa Introduction 349 Switching of Molecular State 351 Azobenzene-Based Chiroptical Photoswitching 354 Diarylethene-Based Chiroptical Switches 359 Electrochiroptical Switching 364 Molecular Switching with Circularly Polarized Light 366 Diastereomeric Photochromic Switches 368 Chiroptical Switching of Luminescence 370 Switching of Supramolecular Organization and Assemblies 372 Molecular Motors 373 Chiral Molecular Machines 374 Making Nanoscale Machines Work 380 Challenges and Prospects 386 References 387 Chiral Nanoporous Materials 391 Wenbin Lin and Suk Joong Lee Classes of Chiral Nanoporous Materials 391 Porous Chiral Metal-Organic Frameworks 392 Porous Oxide Materials 397 Chiral Immobilization of Porous Silica Materials Outlook 406 References 407 Index 411

12 12.1 12.2 12.3 12.4 12.5

400

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Preface
The left- or right-handedness of things chirality to the scientist surrounds us on Earth. The importance of the phenomenon is clear when one considers that, at the submicroscopic scale, it can have either dramatic and triumphal or tragic consequences in and around us. Preparation of chiral systems and the effects they produce are vital for certain chemical processes, such as catalysis, and physical phenomena, such as the switching in displays. Understanding and inuencing these processes at the atomic and molecular level the nanometer scale is essential for their development. This book sets out to explain the foundations of the formation and characterization of asymmetric structures as well as the effects they produce, and reveals the tremendous insight the tenets and tools of nanoscience provide to help in understanding them. The chapters trace the development of the preparative methods used for the creation of chiral nanostructures, in addition to the experimental techniques used to characterize them, and the surprising physical effects that can arise from these minuscule materials. Every category of material is covered, from organic, to coordination compounds, metals and composites, in zero, one, two and three dimensions. The structural, chemical, optical, and other physical properties are reviewed, and the future for chiral nanosystems is considered. In this interdisciplinary area of science, the book aims to combine physical, chemical and material science views in a synergistic way, and thereby to stimulate further this rapidly growing area of science. The rst chapter is an overview of chirality and all the phenomena related with it, written by one of the most eminent present-day authorities on stereochemistry, Laurence Barron from the University of Glasgow. With the scene set, the views of chirality in different systems of increasing dimensionality are covered. In zero dimensions, well-dened supramolecular clusters formed by purely organic and metallo-organic complexes are elegantly presented by Alessandro Scarso and Giuseppe Borsato (Universit C Foscari di Venezia) and the preparation and properties of chiral nanoparticles of all types, and the many exciting challenges associated with them, are reviewed comprehensively by Cyrille Gautier and Thomas Brgi (Universit de Neuchtel). The expression of chirality in essentially one-dimensional objects of a supramolecular or covalent kind has been observed widely in gels and polymers. For the gel

Chirality at the Nanoscale: Nanoparticles, Surfaces, Materials and more. Edited by David B. Amabilino Copyright 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-32013-4

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systems Sudip Malik, Norifumi Fujita and Seiji Shinkai from Kyushu University (Japan) provide an enlightening vision of when, where and how chirality is seen. My close colleague Teresa Sierra from the Materials Science Institute in Saragossa (CSIC) provides an authoritative and comprehensive view of the many aspects of chiral induction in polymeric systems, one of the most prolic areas of research in terms of chiral induction phenomena, and one that affords many opportunities that remain to be exploited in terms of nanoscale materials. Two-dimensional systems are extremely interesting for exploring the transmission of chirality, both because of their symmetry requirements, which limit packing possibilities, as well as for the range of techniques that exist for probing them. This situation is made patently clear in the chapters by Rasmita Raval (University of Liverpool) who describes research done on metal surfaceadsorbate systems, Steven De Feyter, Patrizia Iavicoli, and Hong Xu (Katholieke Universiteit Leuven and ICMAB CSIC), who summarize chirality in physisorbed monolayers in solution, and Isabelle Weissbuch, Leslie Leiserowitz and Meir Lahav (Weizmann Institute of Science, Rehovot) who provide an overview of the tremendous contributions they and others have made to the exploration of chirality in Langmuir-type monolayer systems. These complementary chapters show just how much the tools of nanoscience can reveal about the transfer and expression of chirality in low-dimensional systems, an area that is truly blossoming at the present time. The creation and manifestations of handedness in bulk uids and solids are then reviewed, with special emphasis on the mechanisms of induction of chirality with a view at the scale of nanometers. Carsten Tschierske (Martin-Luther-University HalleWittenberg, Germany) provides an instructive overview of the occurrence of chirality in liquid-crystal systems, in which many remarkable effects are witnessed, and perhaps where nanoscientists can draw inspiration. The supramolecular and thermodynamic aspects of chiral bulk crystals, where a wealth of valuable information can be gleaned in terms of structure and phenomenology, are the subject of an extensive review by Grard Coquerel (Universit de Rouen) and myself. In particular, the construction of phase diagrams is shown to be a crucial part of understanding chiral selection in crystalline systems. This part concludes the path through the structures of different chiral systems. In the remaining chapters, particular properties of chiral nanoscale systems are divulged. Wesley R. Browne, Dirk Pijper, Michael M. Pollard and Ben Feringa (University of Groningen) provide an accessible expert view of chiral molecular machines and switches, perhaps one of the most attractive areas in contemporary stereochemistry. Finally, Wenbin Lin and Suk Joong Lee (University of North Carolina, USA) review another fascinating family of materials, that of chiral nanoporous solids, in which spaces available for molecular recognition and catalysis are available. Thus, the exceptional contributions and their combination in this volume make a unique and useful resource for those entering or established in research concerning stereochemical aspects of nanoscale systems. This book came about largely because of the Marie Curie Research Training Network CHEXTAN (Chiral Expression and Transfer at the Nanoscale) funded by the European Commission. The Network, coming to its end as these lines are

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written, brought together eight groups some of which contribute to this book with the aim of training young scientists in this interdisciplinary area of science. I thank wholeheartedly all those who participated in the Network the senior scientists and excellent group of young researchers for helping to give an impetus to the area. As a consequence of the Network, the International Conference Chirality at the Nanoscale was held (in Sitges, Spain in September 2007) and proved to be a signicant stimulus to thinking for many of the groups working on nanosystems and chirality. I thank everyone who helped make that meeting a success, the lecturers and all the participants, and for such a special moment. I have to thank the Spanish Research Council (the CSIC) who employs me, the staff of the Barcelona Materials Science Institute (ICMAB) for providing such a pleasant environment to work in, and everyone in the Molecular Nanoscience and Organic Materials Department for the healthy environment in which to carry out research. Finally, and most importantly, I am indebted to all the authors for the great effort they have put into producing these excellent summaries that make up the book. With the many pressures we have to write nowadays it is difcult to dedicate time to this kind of enterprise, but they collaborated magnicently and the combined effort is one that I hope you, the readers will appreciate. Institut de Cincia de Materials de Barcelona (CSIC) September 2008

David Amabilino

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List of Contributors
David B. Amabilino Institut de Cincia de Materials de Barcelona (CSIC) Campus Universitari de Bellaterra 08193 Cerdanyola del Valls Catalonia Spain Laurence D. Barron Department of Chemistry University of Glasgow Glasgow G12 8QQ UK Giuseppe Borsato Universit Ca Foscari di Venezia Dipartimento Chimica Dorsoduro 2137 30123 Venezia Italy Wesley R. Browne Stratingh Institute for Chemistry & Zernike Institute for Advanced Materials Faculty of Mathematics and Natural Sciences University of Groningen, Nijenborgh 4 9747 AG Groningen The Netherlands Thomas Brgi Institute for Physical Chemistry Rupert-Karls University Heidelberg Im Neuenheimer Feld 253 69120 Heidelberg Germany Grard Coquerel UC2M2, UPRES EA 3233 Universit de Rouen-IRCOF 76821 Mont Saint Aignan Cedex France Steven De Feyter Laboratory of Photochemistry and Spectroscopy Molecular and Nano Materials Department of Chemistry, and INPAC Institute for Nanoscale Physics and Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200-F 3001 Leuven Belgium

Chirality at the Nanoscale: Nanoparticles, Surfaces, Materials and more. Edited by David B. Amabilino Copyright 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-32013-4

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List of Contributors

Ben L. Feringa Stratingh Institute for Chemistry & Zernike Institute for Advanced Materials Faculty of Mathematics and Natural Sciences University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands Norifumi Fujita Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University Moto-oka 744, Nishi-ku Fukuoka 819-0395 Japan Cyrille Gautier Universit de Neuchtel Institut de Microtechnique Rue Emile-Argand 11 2009 Neuchtel Switzerland Patrizia Iavicoli Institut de Cincia de Materials de Barcelona (CSIC) Campus Universitari 08193 Bellaterra Catalonia Spain Meir Lahav Department of Materials and Interfaces Weizmann Institute of Science 76100-Rehovot Israel

Suk Joong Lee Department of Chemistry CB#3290 University of North Carolina at Chapel Hill NC 27599 USA Leslie Leiserowitz Department of Materials and Interfaces Weizmann Institute of Science 76100-Rehovot Israel Sudip Malik Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University Moto-oka 744, Nishi-ku Fukuoka 819-0395 Japan Dirk Pijper Stratingh Institute for Chemistry & Zernike Institute for Advanced Materials Faculty of Mathematics and Natural Sciences University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands

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XIX

Michael M. Pollard Stratingh Institute for Chemistry & Zernike Institute for Advanced Materials Faculty of Mathematics and Natural Sciences University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands Rasmita Raval The Surface Science Research Centre and Department of Chemistry University of Liverpool Liverpool, L69 3BX UK Alessandro Scarso Universit Ca Foscari di Venezia Dipartimento di Chimica Dorsoduro 2137 30123 Venezia Italy Seiji Shinkai Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University Moto-oka 744, Nishi-ku Fukuoka 819-0395 Japan Teresa Sierra Instituto de Ciencia de Materiales de Aragn Facultad de Ciencias Universidad de Zaragoza-CSIC Zaragoza-50009 Spain

Wenbin Lin Department of Chemistry CB#3290 University of North Carolina at Chapel Hill NC 27599 USA Carsten Tschierske Institute of Chemistry Martin-Luther University Halle Kurt-Mothes Str. 2 06120 Halle Germany Isabelle Weissbuch Department of Materials and Interfaces Weizmann Institute of Science 76100-Rehovot Israel Hong Xu Laboratory of Photochemistry and Spectroscopy Molecular and Nano Materials Department of Chemistry, and INPAC Institute for Nanoscale Physics and Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200-F 3001 Leuven Belgium

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List of Abbreviations
AFM AIEE APS BAR CCW CD CLG CN CPL CPL CW CYA 1D 2D 3D DFT DSC 2DSD ECD ee EM EPJ EPL FE-SEM FLC GIXD HBC HTP IUPAC LB LC LC LDH atomic force microscopy aggregate-induced enhanced emission aminopropyltrimethoxysilane barbiturates counterclockwise circular dichroism cholesteryl-S-glutamate cinchonine circularly polarized light circular polarization of luminescence clockwise cyanurate one dimensional two-dimensional three-dimensional Density functional theory differential scanning calorimetry two-dimensional structural database electronic circular dichroism enantiomeric excess electron microscopy European Physical Journal elliptically polarized light eld emission scanning electron microscopy ferroelectric liquid crystals grazing-incidence X-ray diffraction hexabenzocoronenes helical twisting power International Union of Pure and Applied Chemistry Langmuir-Blodgett liquid crystal(line) liquid crystalline layered double hydroxides

Chirality at the Nanoscale: Nanoparticles, Surfaces, Materials and more. Edited by David B. Amabilino Copyright 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-32013-4

XXII

List of Abbreviations

LEED LMW LMWG MALDI-TOF MS MBETs MD ML MOFs N-LC NIC NIR NPs NRDs ONPs ORD PAGE PS PVA PVED QSEs RA RAIRS ROA RW SEC SP STM Tm TA TEOS THF TOAB TPP TTF UHV VCD VDSA WORM XPD XPS

low-energy electron diffraction Low molecular weight low molecular weight gelators matrix-assisted laser desorption-ionization time-of-ight mass spectrometry metal-based electronic transitions Marks decahedron monolayers metalorganic frameworks nematic LC N-isobutyryl-cysteine near-infrared nanoparticles nanorods organic nanoparticles optical rotatory dispersion polyacrylamide gel electrophoresis polystyrene poly(vinyl alcohol) parity-violating energy difference quantum size effects resolving agent reection absorption infrared spectroscopy Raman optical activity re-writable size exclusion chromatography surface plasmon scanning tunnelling microscopy melting temperature tartaric acid tetraethoxylsilane tetrahydrofuran tetraoctylammonium bromide triphenylphosphine tetrathiafulvalene ultra-high vacuum vibrational circular dichroism vapor-driven self-assembly write-once read many X-ray photoelectron diffraction X-ray photoelectron spectroscopy