Chirality at the nanoscale: nanoparticles, surfaces, materials and more
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| Format: | Book |
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| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2009
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XXII, 418 S. Ill., graph. Darst. |
| ISBN: | 9783527320134 |
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| 245 | 1 | 0 | |a Chirality at the nanoscale |b nanoparticles, surfaces, materials and more |c ed. by David B. Amabilino |
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| adam_text | Titel: Chirality at the nanoscale
Autor: Amabilino, David B.
Jahr: 2009
Contents
Preface XIII
List of Contributors XVII
List of Abbreviations XXI
1 An Introduction to Chirality at the Nanoscale 1
Laurence D. Barron
1.1 Historical Introduction to Optical Activity and Chirality 1
1.2 Chirality and Life 4
1.2.1 Homochirality 4
1.2.2 Pasteur s Conjecture 7
1.3 Symmetry and Chirality 8
1.3.1 Spatial Symmetry 8
1.3.2 Inversion Symmetry: Parity, Time Reversal and Charge Conjugation 9
1.3.3 True and False Chirality 10
1.3.4 Symmetry Violation 14
1.3.5 Symmetry Violation versus Symmetry BreaMng 16
1.3.6 Chirality in Two Dimensions 17
1.4 Absolute Enantioselection IS
1.4.1 Truly Chiral Influences IS
1.4.2 Falsely Chiral Influences 20
15 Spectroscopic Probes of Chirality in Nanosystems 21
1.5.1 Electronic Optical Activity 22
1.5.2 Vibrational Optical Activity 23
1-6 Conclusion 24
References 24
2 Optically Active Supramolecules 29
ASessandro Scarso and Giuseppe. Borsato
2.1 Introduction to Supramolecular Stereochemistry 29
2.1.1 Survey of Weak Intermolecular Attractive Forces 31
2.1.2 Timescale of Supramolecular Interactions and Racemization
Processes 33
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
VI Contents
2.2 Self-Assembly of Intrinsically Chiral Molecular Capsules 37
2.2.1 Hydrogen-Bonded Assemblies 37
2.2.1.1 Double Rosettes 37
2.2.1.2 Hydrogen-Bonded Capsules 39
2.2.2 Metal-ligand Assemblies 43
2.3 Chiral Induction m the Formation of Supramolecular Systems 46
2.3.1 Chiral Memory Effect in Hydrogen-Bonded Assemblies 46
2.3.2 Chiral Memory Effect in Metal-Ligand Assemblies 49
2.4 Chiral Spaces for Chiral Recogninon 51
2.4.1 Enantioselective Recognition within Chiral Racemic
Self-Assembled Hosts 52
2.4.1.1 Hydrogen-Bonded Hosts 52
2.4.1.2 Metal-Ligand Hosts 53
2.4.2 Interguests Chiral Sensing within Achiral Self-Assembled Hosts 56
2.4.2.1 Hydrogen-Bonded Hosts 57
2.4.2.2 Metal-Ligand Hosts 60
2.5 Conclusion and Outlook 61
References 62
3 Chiral Nanoparticles 67
Cyrille Gautier and Thomas Bürgi
3.1 Introduction 67
3.2 Nanoparticle Properties and Synthesis 68
3.2.1 Nanoparticle Properties 68
3.2.2 Preparation, Purification and Size Separation 71
3.2.2.1 Preparation 71
3.2.3 Purification and Separation of Nanoparticles 74
3.3 Chiroptical Properties of Inorganic Nanoparticles 74
3.3.1 Vibrational Circular Dichroism 74
3.3.2 Circular Dichroism 75
3.3.3 Origin of Optical Activity in Metal-Based Transitions 78
3.4 Optically Active Coordination Clusters 80
3.5 Nanoparticles of Chiral Organic Compounds 81
3.6 Applications 83
3.6.1 Asymmetrie Catalysis 83
3.6.2 Nanoparticles in Liquid-Crystal Media 85
3.6.3 Chiral Discrimination 87
3.7 Outlook 87
References 87
4 Gels as a Media for Functional Chiral Nanofibers 93
Sudip Malik, Norifumi Fujita, and Seiji Shinkai
4.1 A Brief Introduction to Gels 93
4.1.1 Introduction 93
4.1.2 Definition of Gels 94
Contents VII
4.1.3 Classification of Gels 94
4.1.4 Chirality in Gels 95
4.2 Chiral Organogels 96
4.2.1 Steroid-Based Chiral Gelators 96
4.2.2 Pyrene-Based Chiral Gelators 103
4.2.3 Diaminoydohexane-Based Chiral Gelators 103
4.2.4 OPV-Based Chiral Gelators 105
4.3 Chiral Hydrogels 108
4.3.1 Chiral Fatty Acids 108
4.3.2 Chiral Sugar-Based Gelators 109
4.3.3 Miscellaneous Chiral Hydrogelators 110
4.3.3.1 The Future of Chiral Gels in Nanoscience and Nanotechnology 111
References 111
5 Expression of Chirality in Polymers 115
Teresa Sierra
5.1 Histoncal Perspective on Chiral Polymers 115
5.2 Chiral Architecture Control in Polymer Synthesis 117
5.2.1 Polymenzation of Chiral Assemblies 117
5.2.1.1 Chiral Organization Through H-Bondmg Interactions 118
5.2.1.2 Chiral Organization Through n-Stackmg Interactions 120
5.2.1.3 Chiral Organization Through Mesogenic Drivmg Forces 121
5.2.2 Control of Chiral Architecture During Polymenzation 123
5.2.2.1 Polymenzation in Chiral Solvents 123
5.2.2.2 Polymenzation with Chiral Templates 127
5.2.2.3 Polymerization of Chiral Assemblies by Circularly Polarized
Radiation 128
5.2.3 Chiral Architecture Control upon Polymerization: Noncovalent
Interactions 129
5.2.3.1 Control ofthe Chiral Architecture by H-Bondmg Interactions 129
5.2.3.2 Control ofthe Chiral Architecture by n-Stacking and Steric Factors 133
5.2.3.3 Chiral Superstructures by 7i-Interactions: Chiral Aggregates 134
5.3 Asymmetry Induction in Nonchiral Polymers 137
5.3.1 Induction Through Noncovalent Interaction with Chiral Molecules 137
5.3.1.1 Chiral Induction by Acid-Base Interactions 137
5.3.1.2 Chiral Induction by Host-Cation Interactions 143
5.3.1.3 Chiral Induction by Metal Coordination 143
5.3.2 Induction Through Noncovalent Interaction with Chiral Polymers 146
5.3.3 Induction Through the Formation of Inclusion Complexes 147
5.3.4 Induction by a Chiral External Stimulus 150
5.3.4.1 Solvent-Induced Chirality 150
5.3.4.2 LighMnduced Chirality 151
5.4 Chiral Memory Effects. Tuning Helicity 154
5.4.1 Memory Effects from Chiral Polymers 154
5.4.1.1 Temperature- and/or Solvent-Driven Memory Effects 154
VIII Contents
5.4.1.2 Light-Dnven Memory Effects 157
5.4.2 Memory Effects from Achiral Polymers 158
5.5 Chiral Block-Copolymers and Nanoscale Segregation 161
5.5.1 Chiral Block-Copolymers: Nanoscale Segregation in the Bulk 162
5.5.2 Chiral Block-Copolymers: Nanoscale Segregation in the Mesophase 162
5.5.3 Chiral Block-Copolymers: Nanoscale Segregation in Solvents.
Amphiphilic Block-Copolymers 165
5.6 Templates for Chiral Objects 169
5.6.1 Templates for Chiral Supramolecular Aggregates 169
5.6.1.1 Templating with Natural Helical Polymers 169
5.6.1.2 Templating with Synthetic Helical Polymers 172
5.6.2 Molecular Imprinting with Helical Polymers 174
5.6.3 Templating by Wrapping with Helical Polymers 175
5.6.4 Alignment of Functional Groups 176
5.6.4.1 Polyisocyamdes 176
5.6.4.2 Polypeptides 178
5.6.4.3 Polyacetylenes 178
5.6.4.4 Foldamers 179
5.7 Outlook 180
References 181
6 Nanoscale Exploration of Molecular and Supramolecular Chirality
at Metal Surfaces under Ultrahigh-Vacuum Conditions 191
Rasmita Raval
6.1 Introduction 191
6.2 The Creation of Surface Chirality in 1D Superstructures 192
6.3 The Creation of2D Surface Chirality 196
6.3.1 2D Supramolecular Chiral Clusters at Surfaces 196
6.3.2 2D Covalent Chiral Clusters at Surfaces 199
6.3.3 Large Macroscopic 2-D Chiral Arrays 200
6.3.4 Chiral Nanocavity Arrays 204
6.4 Chiral Recognition Mapped at the Single-Molecule Level 205
6.4.1 Homochiral Seif-Recognition 205
6.4.2 Diastereomenc Chiral Recognition 207
6.4.2.1 Diastereomeric Chiral Recognition by Homochiral Structures 207
6.4.2.2 Diastereomeric Chiral Recognition by Heterochiral Structures 209
6.5 Summary 211
References 212
7 Expression of Chirality in Physisorbed Monolayers Observed
by Scanning Tunneling Microscopy 215
Steven De Feyter, Patrizia lavicoli, and Hong Xu
7.1 Introduction 215
7.2 How to Recognize Chirality at the liquid/Solid Interface 217
7.2.1 Chirality at the Level of the Monolayer Symmetry 217
Contents IX
7.2.2 Chirality at the Level of the Monolayer - Substrate Orientation 219
7.2.3 Determination Absolute Configuration 220
7.3 Chirality in Monolayers Composed of Enantiopure Molecules 221
7.4 Polymorphism 228
7.5 Is Chirality Always Expressed? 230
7.6 Racemic Mixtures: Spontaneous Resolution? 231
7.6.1 Chiral Molecules 231
7.6.2 Achiral Molecules 234
7.7 Multicomponent Structures 237
7.8 Physical Fields 240
7.9 Outlook 240
References 243
8 Structure and Function of Chiral Architectures of Amphiphilic
Molecules at the Air/Water Interface 247
Isabelle Weissbuch, Leslie Leiserowitz, and Meir Lahav
8.1 An introduction to Chiral Monolayers on Water Surface 247
8.2 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
8.3 Langmuir Monolayers of Amphiphilic a-Ammo Acids 249
8.3.1 Domain Morphology and Energy Calculations in Monolayers
of N-acyl-cc-Amino Acids 253
8.4 Stochastic Asymmetric Transformations in Two Dimensions at the
Water Surface 254
8.5 Self-Assembly of Diastereoisomeric Films at the Air/Water
Interface 255
8.6 Interactions of the Polar Head Groups with the Molecules of the
Aqueous Environment 256
8.7 Interdigitated Bi- or Multilayer Films on the Water Surface 261
8.8 Structural Transfer from 2D Monolayers to 3D Crystals 263
8.9 Homochiral Peptides from Racemic Amphiphilic Monomers at the
Air/Water Interface 265
8.10 Conclusions 268
References 268
9 Nanoscale Stereochemistry in Liquid Crystals 271
Carsten Tschierske
9.1 The Liquid-Crystalline State 271
9.2 Chirality in Liquid Crystals Based on Fixed Molecular Chirality 273
9.2.1 Chiral Nematic Phases and Blue Phases 274
9.2.2 Chirality in Smectic Phases 276
9.2.3 Polar Order and Switching in Chiral LC Phases 276
9.2.3.1 Ferroelectric and Antiferroelectric Switching 276
9.2.3.2 Electroclinic Effect 279
X Contents
9.2.3.3 Electric-Field-Driven Deracemization 279
9.2.4 Chirality Transfer via Guest-Host Interactions 279
9.2.5 Induction of Phase Chirality by External Chiral Stimuli 281
9.2.6 Chirality in Columnar LC Phases 282
9.3 Chirality Due to Molecular Self-Assembly of Achiral Molecules 284
9.3.1 Helix Formation in Columnar Phases 284
9.3.2 Helical Filaments in Lamellar Mesophases 287
9.4 Polar Order and Chirality in LC Phases Formed by Achiral
Bent-Core Molecules 288
9.4.1 Phase Structures and Polar Order 288
9.4.2 Superstructural Chirality and Diastereomerism 290
9.4.3 Switching of Superstructural Chirality 291
9.4.4 Macroscopic Chirality and Spontaneous Reflection Symmetry
Breaking in Banana Phases 292
9.4.4.1 Layer Chirality 292
9.4.4.2 Dark Conglomerate Phases 292
9.5 Spontaneous Reflection-Symmetry Breaking in Other LC Phases 295
9.5.1 Chirality in Nematic Phases of Achiral Bent-Core Molecules 295
9.5.2 Spontaneous Resolution of Racemates in LC Phases of Rod-Like
Mesogens 295
9.5.3 Deracemization of Fluxional Conformers via Diastereomeric
Interactions 296
9.5.4 Chirality in Nematic, Smectic and Cubic Phases of Achiral
Rod-Like Molecules 296
9.5.5 Segregation of Chiral Conformers in Fluids, Fact or Fiction? 296
9.6 Liquid Crystals as Chiral Templates 298
9.7 Perspective 299
References 299
10 The Nanoscale Aspects of Chirality in Crystal Growth: Structure
and Heterogeneous Equilibria 305
Cirard Coquerel and David B. Amabilino
10.1 An introduction to Crystal Symmetry and Growth for Chiral
Systems. Messages for Nanoscience 305
10.2 Supramolecular Interactions in Crystals 308
10.2.1 Hydrogen Bonds 309
10.2.2 Interaromatic Interactions 310
10.2.3 Electrostatic Interactions 311
10.2.4 Modulation of Noncovalent Interactions with Solvent 312
10.2.5 Polymorphism 312
10.3 Symmetry Breaking in Crystal Formation 312
10.3.1 Spontaneous Resolution of Chiral Compounds 313
10.3.2 Spontaneous Resolution of Achiral Compounds 315
10.4 Resolutions of Organic Compounds 317
Contents XI
10.5 Resolutions of Coordination Compounds with Chiral
Countenons 320
10.6 Thermodynamic Considerations in the Formation of Chiral
Crystals 322
10.6.1 What is the Order of a System Composed of Two Enantiomers? 322
10.6.2 Resolution by Diastereomeric Associations 331
10.7 Influencing the Crystallization of Enantiomers 335
10.7.1 Solvent 335
10.7.2 Preferential Nucleation and Inhibition 336
10.8 Chiral Host-Guest Complexes 338
10.9 Perspectives 341
References 341
11 Switching at the Nanoscale: Chiroptical Molecular Switches
and Motors 349
Wesley R. Browne, Dirk Pijper, Michael M. Pollard, and Ben L Feringa
11.1 Introduction 349
11.2 Switching of Molecular State 351
11.3 Azobenzene-Based Chiroptical Photoswitching 354
11.4 Diarylethene^Based Chiroptical Switches 359
11.5 Electrochiroptical Switching 364
11.6 Molecular Switching with Circularly Polarized Light 366
11.7 Diastereomeric Photochromic Switches 368
11.8 Chiroptical Switching of Luminescence 370
11.9 Switching of Supramolecular Organization and Assemblies 372
11.10 Molecular Motors 373
11.11 Chiral Molecular Machines 374
11.12 Making Nanoscale Machines Work 380
11.13 Challenges and Prospects 386
References 387
12 Chiral Nanoporous Materials 391
Wenbin Lin and Sukjoong Lee
12.1 Classes of Chiral Nanoporous Materials 391
12.2 Porous Chiral Metal-Organic Frameworks 392
12.3 Porous Oxide Materials 397
VIA Chiral Immobilization of Porous Silica Materials 400
12.5 Outlook 406
References 407
Index 411
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| spelling | Chirality at the nanoscale nanoparticles, surfaces, materials and more ed. by David B. Amabilino Weinheim Wiley-VCH 2009 XXII, 418 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Nanostrukturiertes Material (DE-588)4342626-8 gnd rswk-swf Chiralität Chemie (DE-588)4147732-7 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Chiralität Chemie (DE-588)4147732-7 s Nanostrukturiertes Material (DE-588)4342626-8 s DE-604 Amabilino, David B. Sonstige oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017051746&sequence=000004&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Chirality at the nanoscale nanoparticles, surfaces, materials and more Nanostrukturiertes Material (DE-588)4342626-8 gnd Chiralität Chemie (DE-588)4147732-7 gnd |
| subject_GND | (DE-588)4342626-8 (DE-588)4147732-7 (DE-588)4143413-4 |
| title | Chirality at the nanoscale nanoparticles, surfaces, materials and more |
| title_auth | Chirality at the nanoscale nanoparticles, surfaces, materials and more |
| title_exact_search | Chirality at the nanoscale nanoparticles, surfaces, materials and more |
| title_full | Chirality at the nanoscale nanoparticles, surfaces, materials and more ed. by David B. Amabilino |
| title_fullStr | Chirality at the nanoscale nanoparticles, surfaces, materials and more ed. by David B. Amabilino |
| title_full_unstemmed | Chirality at the nanoscale nanoparticles, surfaces, materials and more ed. by David B. Amabilino |
| title_short | Chirality at the nanoscale |
| title_sort | chirality at the nanoscale nanoparticles surfaces materials and more |
| title_sub | nanoparticles, surfaces, materials and more |
| topic | Nanostrukturiertes Material (DE-588)4342626-8 gnd Chiralität Chemie (DE-588)4147732-7 gnd |
| topic_facet | Nanostrukturiertes Material Chiralität Chemie Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017051746&sequence=000004&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT amabilinodavidb chiralityatthenanoscalenanoparticlessurfacesmaterialsandmore |