Li / Wu Hydrogen Bonded Supramolecular Structures

2015
ISBN: 978-3-662-45756-6
Verlag: Springer
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, Band 87, 357 Seiten

Reihe: Lecture Notes in Chemistry

This book covers the advances in the studies of hydrogen-bonding-driven supramolecular systems  made over the past decade. It is divided into four parts, with the first introducing the basics of hydrogen bonding and important hydrogen bonding patterns in solution as well as in the solid state. The second part covers molecular recognition and supramolecular structures driven by hydrogen bonding. The third part introduces the formation of hollow and giant macrocycles directed by hydrogen bonding, while the last part summarizes hydrogen bonded supramolecular polymers.This book is designed to bring together in a single volume the many important aspects of hydrogen bonding supramolecular chemistry and will be a valuable resource for graduates and researchers working in supramolecular and related sciences.Zhan-Ting Li, PhD, is a Professor of Organic Chemistry at the Department of Chemistry, Fudan University, China.Li-Zhu Wu, PhD, is a Professor of Organic Chemistry at the Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, China.

Zhan-Ting Li was born in China in 1966. He received his BS in 1985 from Zhengzhou University and his PhD in organic fluorine chemistry in 1992 under the direction of Prof. Qing-Yun Chen at the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. Following postdoctoral research stays with Prof. Jan Becher at the University of South Denmark and Prof. Steven C. Zimmerman at the University of Illinois at Urbana-Champaign, he served as an Associate Professor and later Full Professor at the SIOC (1996-2010). In 2010, he switched to his present position as a Full Professor at the Department of Chemistry, Fudan University in Shanghai. Prof. Li has co-authored more than 190 peer-reviewed papers and 10 book chapters. His research interests include hydrogen bonding-mediated biomimetic structures and molecular recognition, and conjugated and self-assembled porous structures and functions.Li-Zhu Wu received her BS from Lanzhou University (1990) and PhD from the Technical Institute of Physics and Chemistry (TIPC), Chinese Academy of Sciences (1995) under the direction of Prof. Chen-Ho Tung. She worked as a postdoctoral researcher with Prof. Chi-Ming Che at the University of Hong Kong (1997-1998) and has been a Full Professor at the TIPC since 1998. Prof. Wu has published over 200 research papers, reviews and book chapters. Her research focuses on photochemical conversion, including artificial photosynthesis, visible light-catalysis for efficient and large-scale organic synthesis, photoinduced electron transfer, and energy transfer and chemical reactions in supramolecular systems. She is currently a member of the Editorial Advisory Board of Inorganic Chemistry and Langmuir of ACS.

Autoren/Hrsg.

Li, Zhan-Ting

Li, Zhanting

Wu, Li-Zhu

Inhaltsverzeichnis

1;Preface;6
2;Contents;8
3;1 Hydrogen Bonding Motifs: New Progresses;13
3.1;Abstract;13
3.2;1.1 Hydrogen Bonding: The Basic Aspects;13
3.2.1;1.1.1 Definition;13
3.2.2;1.1.2 Hydrogen Bonding Donors and Acceptors;14
3.2.3;1.1.3 The Strength of the Hydrogen Bond;15
3.2.4;1.1.4 Hydrogen Bonding Formed by a Single Functional Group;17
3.3;1.2 Intramolecular Hydrogen Bonding;25
3.3.1;1.2.1 The O--H00B700B700B7X Hydrogen Bonding;25
3.3.2;1.2.2 The N--H00B700B700B7X Hydrogen Bonding;26
3.4;1.3 Intermolecular Hydrogen Bonding;36
3.4.1;1.3.1 Double Hydrogen Bonding;36
3.4.2;1.3.2 Triple Hydrogen Bonding;37
3.4.3;1.3.3 Quadruple Hydrogen Bonding;39
3.5;1.4 Conclusion;45
3.6;Acknowledgments;45
3.7;References;46
4;2 Understanding of Noncovalent Interactions Involving Organic Fluorine;49
4.1;Abstract;49
4.2;2.1 Introduction;49
4.2.1;2.1.1 Why Fluorine Is So Special?;51
4.3;2.2 Debate on Participation of Fluorine as a Hydrogen Bond Donor: Overview of the Weak X--H00B700B700B7F--C; X = N, O, C Hydrogen Bond;52
4.4;2.3 Inputs from Other Interactions Involving Organic Fluorine;65
4.4.1;2.3.1 Insight into Halogen--Halogen Interactions Involving Fluorine;65
4.4.2;2.3.2 Insights into Halogen Bond Formation Involving Fluorine (C--F00B700B700B7X; X = Halogen, N, O, S);69
4.5;2.4 Conclusions;73
4.6;Acknowledgments;74
4.7;References;74
5;3 Hydrogen Bonding in Supramolecular Crystal Engineering;80
5.1;Abstract;80
5.2;3.1 Introduction;80
5.3;3.2 Crystal Engineering Strategies;82
5.3.1;3.2.1 Supramolecular Synthons and Retrosynthesis;82
5.3.2;3.2.2 Reticular Synthesis;83
5.4;3.3 Hydrogen Bonding;84
5.4.1;3.3.1 Definition and Scopes;84
5.4.2;3.3.2 Description of Hydrogen Bonding Motifs: The Graph Sets;85
5.4.3;3.3.3 Hydrogen Bonding Rules;86
5.5;3.4 Interpenetration;86
5.6;3.5 Hydrogen Bonding Structures;88
5.6.1;3.5.1 Discrete Hydrogen Bonding Capsules;88
5.6.1.1;3.5.1.1 Dimeric Capsules;89
5.6.1.2;3.5.1.2 Hexameric Capsules;91
5.6.1.3;3.5.1.3 A Quasi-truncated Octahedron;94
5.6.2;3.5.2 1D Infinite Hydrogen Bonding Nanotubes;95
5.6.2.1;3.5.2.1 Tubes Constructed from Flat Macrocycles;96
5.6.2.2;3.5.2.2 Tubes Constructed from Calixarenes;98
5.6.2.3;3.5.2.3 Tubes Constructed from Acyclic Molecules;99
5.6.3;3.5.3 2D and 3D Borromean Arrayed Organic Crystals;101
5.6.4;3.5.4 2D 2192 3D Parallel Polycatenated Structures;104
5.6.5;3.5.5 3D Interpenetrated dia and pcu Frameworks;106
5.6.6;3.5.6 Unusual Aggregation Phase of Water Molecules;107
5.7;3.6 Applications;110
5.7.1;3.6.1 Crystal Engineering of Solid State Photochemical Reactions;110
5.7.1.1;3.6.1.1 Self-complementary Reactants;110
5.7.1.2;3.6.1.2 Auxiliary Templates;111
5.7.1.3;3.6.1.3 Confined Environments of Cavities;113
5.7.2;3.6.2 Gas Adsorption and Separation;114
5.7.3;3.6.3 Crystal Engineering of Pharmaceutical Cocrystals;116
5.8;References;118
6;4 Hydrogen Bonding-Mediated Self-assembly of Aromatic Supramolecular Duplexes;125
6.1;Abstract;125
6.2;4.1 Introduction;125
6.3;4.2 Oligoamide-Based Molecular Duplex Strands;126
6.3.1;4.2.1 Oligoamide-Based Molecular Duplex Strands;126
6.3.2;4.2.2 Applications;128
6.4;4.3 Oligohydrazide-Based Molecular Duplex Strands;132
6.4.1;4.3.1 From Supramolecular Zipper to Quadruple Hydrogen-Bonded Heterodimer;133
6.4.2;4.3.2 Strict Self-complementary Oligohydrazide-Based Duplexes;134
6.4.3;4.3.3 Shuttle Movement;135
6.4.4;4.3.4 Mutual Responsive Low Molecular Mass Organic Gelators;137
6.4.5;4.3.5 Supramolecular Substitution;137
6.4.6;4.3.6 Amide-Urea-Based Molecular Duplexes;138
6.4.7;4.3.7 ``Hao'' Templated Molecular Duplex;141
6.5;4.4 ``Covalent Casting'' Strategy-Based Molecular Duplexes;141
6.6;4.5 Other Molecular Duplex Strands;143
6.7;4.6 Conclusions and Outlook;145
6.8;References;145
7;5 Hydrogen Bonding-Driven Anion Recognition;147
7.1;Abstract;147
7.2;5.1 Introduction;147
7.3;5.2 Amide-Based Anion Recognition;148
7.4;5.3 Urea-Based Anion Recognition;159
7.5;5.4 Pyrrole-Based Anion Recognition;174
7.6;5.5 CH Donor-Based Anion Recognition;185
7.7;5.6 OH-Based Anion Recognition;188
7.8;5.7 Conclusion;191
7.9;References;191
8;6 Formation of Hydrogen-Bonded Self-assembled Structures in Polar Solvents;196
8.1;Abstract;196
8.2;6.1 Introduction;196
8.3;6.2 Nucleobase Pairing and Nanostructure Formation in Water;197
8.4;6.3 Self-sorting/Orthogonal Self-assembly;202
8.5;6.4 Supramolecular Polymers;210
8.6;6.5 Supramolecular Gels in Aqueous and Polar Organic Media;216
8.7;6.6 Vesicles, Bilayers, Micelles Through H-Bonding;223
8.8;References;233
9;7 Hydrogen Bonded Capsules: Chemistry in Small Spaces;235
9.1;Abstract;235
9.2;7.1 Why Study Encapsulated Molecules?;235
9.3;7.2 The Capsules and Their Contents;236
9.3.1;7.2.1 The Tennis Ball;236
9.3.2;7.2.2 The Softball;238
9.3.3;7.2.3 A Cylindrical Capsule;239
9.3.4;7.2.4 The Volleyball;239
9.4;7.3 What's It Like Inside the Capsules?;240
9.5;7.4 How Do Molecules Get In and Out of the Capsules?;242
9.6;7.5 Amplified Intermolecular Forces;243
9.7;7.6 Arrangements in Encapsulation Space: New Stereochemistry;245
9.7.1;7.6.1 Social Isomers;245
9.7.2;7.6.2 Single Molecule Solvation;247
9.7.3;7.6.3 Isotope Effects;247
9.7.4;7.6.4 Constellations;248
9.7.5;7.6.5 Diastereomers;250
9.8;7.7 Chiral Spaces;251
9.9;7.8 Reactivity;253
9.10;7.9 Conclusion;254
9.11;Acknowledgments;254
9.12;References;255
10;8 Hydrogen Bonded Organic Nanotubes;257
10.1;Abstract;257
10.2;8.1 Introduction;257
10.3;8.2 Strategies for the Construction of Hydrogen Bonding-Driven Organic Nanotubes;258
10.4;8.3 Nanotubes from Hydrogen Bonding-Induced Helical Structures;259
10.5;8.4 Nanotubes from Tubular Molecules;262
10.6;8.5 Nanotubes from Hydrogen Bonded Rod-like Molecular Units;264
10.7;8.6 Nanotubes from Hydrogen Bonded Cyclic Molecules;266
10.7.1;8.6.1 Nanotubes from Hydrogen Bonded Cyclic Peptides;266
10.7.2;8.6.2 Nanotubes from Hydrogen Bonded Cyclic Ureas;269
10.8;8.7 Nanotubes from Hydrogen Bonded Wedge- or Sector-like Molecules;270
10.9;8.8 Conclusions and Outlooks;273
10.10;References;273
11;9 H-Bonding-Assisted One-Pot Macrocyclization for Rapid Construction of H-Bonded Macrocyclic Aromatic Foldamers;276
11.1;Abstract;276
11.2;9.1 Introduction;276
11.3;9.2 Concept Formulation;278
11.4;9.3 Aryl Amide Macrocycles;281
11.4.1;9.3.1 Non-fivefold Symmetric Aryl Amide Macrocycles;281
11.4.2;9.3.2 Fivefold Symmetric Aryl Amide Macrocycles;284
11.4.2.1;9.3.2.1 Evolution of Fivefold Symmetric Macrocycles;284
11.4.2.2;9.3.2.2 Fivefold Symmetric Macrocyclic Alkoxybenzene Pentamers;286
11.4.2.3;9.3.2.3 Fivefold Symmetric Macrocyclic Pyridone Pentamers;291
11.4.3;9.3.3 Highly Selective Production of Strained Aromatic Hexamers;295
11.4.4;9.3.4 Chemo- and Regio-Selective Demethylations;299
11.5;9.4 Macrocycles Containing Non-amide Linkages;300
11.6;9.5 Mechanism of One-Pot Macrocyclization;304
11.6.1;9.5.1 Variable Functionalizations Around the Pentameric Periphery;305
11.6.2;9.5.2 A Chain-Growth Mechanism Underlying the Formation of Aromatic Pentamers;309
11.6.3;9.5.3 A Non-chain Growth Mechanism Underlying the Formation of Strained Aromatic Hexamers and Heptamers;318
11.7;9.6 Conclusion;323
11.8;References;324
12;10 Hydrogen-Bonded Supramolecular Polymers;328
12.1;Abstract;328
12.2;10.1 Introduction;328
12.3;10.2 Hydrogen-Bonding Building Blocks;330
12.4;10.3 Hydrogen-Bonded Main-Chain Supramolecular Polymers Constructed by Low-Molecular-Weight Monomers;334
12.5;10.4 Hydrogen-Bonded Supramolecular Polymers Constructed by High-Molecular-Weight Conventional Polymers that Are Functionalized by Hydrogen-Bonded Motifs;341
12.5.1;10.4.1 Telechelic Supramolecular Polymers;341
12.5.2;10.4.2 ``Side-Chain'' Supramolecular Polymer Networks;344
12.6;10.5 Supramolecular Polymers Constructed by Orthogonal Hydrogen Bonding-Driven Self-assembly and Other Non-covalent Interactions;347
12.7;10.6 Conclusions;355
12.8;References;356