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Book Details
Abstract
The past decade has seen significant advances in naphthalenediimide and rylene diimide chemistry. This book discusses the recent advances in this field, and highlights potential and real applications for the molecules. Such applications include organic photovoltaics, anion-slides, DNA binders, and building blocks for complex molecular topologies.
Naphthalenediimide and its Congeners is the first book in this rapidly developing area, and will be essential reference material for postdoctoral researchers and postgraduate students. This text will also provide a solid foundation for further development of naphthalenediimide chemistry.
Written by leaders in the field, the book includes chapters on the supramolecular chemistry of naphthalenediimide; DNA intercalators; ion transport through membranes; naphthalenediimide based photovoltaics; and rylene dyes, amongst others. Naphthalenediimide and its Congeners is a detailed and in depth resource relevant not only to supramolecular and materials chemists, but also to the larger chemistry and materials science fields.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Preface | v | ||
| Dedication | vii | ||
| Contents | ix | ||
| Chapter 1 Supramolecular Chemistry of Naphthalenediimide and its Congeners | 1 | ||
| 1.1 Introduction | 1 | ||
| 1.2 Molecules with Complex Topologies | 3 | ||
| 1.3 Clathrates and Rigid Molecules | 17 | ||
| 1.4 Supramolecular Nanotubes and Receptors | 20 | ||
| 1.5 Biological Applications | 26 | ||
| 1.6 Sensors | 29 | ||
| 1.7 Dyads and Triads for Electron Transfer Studies | 31 | ||
| 1.8 Conclusions | 32 | ||
| References | 33 | ||
| Chapter 2 NDI as a DNA Intercalator | 37 | ||
| 2.1 DNA as a Drug Target | 37 | ||
| 2.2 Overview of DNA Binding Motifs | 38 | ||
| 2.2.1 DNA Structure | 38 | ||
| 2.2.2 Triplex-forming Oligonucleotides | 40 | ||
| 2.2.3 Peptide Nucleic Acid | 42 | ||
| 2.2.4 Minor Groove-binding Polyamides | 42 | ||
| 2.3 Intercalation | 43 | ||
| 2.3.1 Monointercalators | 46 | ||
| 2.3.2 Bisintercalators | 50 | ||
| 2.3.3 NDI Combilexins | 52 | ||
| 2.3.4 Longer Polyintercalator Derivatives | 53 | ||
| 2.4 Threading NDI Polyintercalators | 54 | ||
| 2.4.1 Synthesis | 55 | ||
| 2.4.2 Sequence-specific NDI Bisintercalators | 56 | ||
| 2.4.3 Sequence-specific NDI Tetra- and Hexaintercalators | 59 | ||
| 2.5 Conclusion | 66 | ||
| References | 66 | ||
| Chapter 3 NDI Foldamers, Assemblies and Conformational Switching | 72 | ||
| 3.1 Introduction | 72 | ||
| 3.2 Theory Behind Interactions Between Aromatic Groups | 73 | ||
| 3.2.1 ‘‘Polar/Pi\" Model | 73 | ||
| 3.2.2 ‘‘Local, Direct Interaction\" Model | 74 | ||
| 3.3 Electron-rich/Electron-deficient and Electron-rich/Electron-rich Systems | 76 | ||
| 3.3.1 Interactions Between Aromatic Groups in Aqueous Solution | 76 | ||
| 3.3.2 Survey of Supramolecular Systems | 78 | ||
| 3.4 Systems That Undergo Stacking Geometry Switching | 80 | ||
| 3.4.1 Synthetic Ion Channel | 80 | ||
| 3.4.2 Self-sorting DAN and NDI Monomers | 82 | ||
| 3.4.3 Synthetic Amyloid Fibrils | 82 | ||
| 3.4.4 Mesophases Exhibiting Switching Behavior | 83 | ||
| 3.5 Outlook | 87 | ||
| References | 87 | ||
| Chapter 4 Naphthalenediimide in Modular Columnar Liquid Crystals: Key Component of Donor-Acceptor Columnar Liquid Crystals | 90 | ||
| 4.1 Liquid Crystals: Brief Overview | 90 | ||
| 4.1.1 Calamitic Liquid Crystals | 91 | ||
| 4.1.2 Discotic Liquid Crystals | 92 | ||
| 4.1.3 Liquid Crystal Characterization | 95 | ||
| 4.2 Columnar Liquid Crystals and Aromatic Donor-Acceptor Interactions | 96 | ||
| 4.2.1 Stability in Columnar Liquid Crystals | 96 | ||
| 4.2.2 Aromatic Donor-Acceptor Interactions | 97 | ||
| 4.2.3 Aromatic Donor-Acceptor-Based Mesophases | 99 | ||
| 4.3 Naphthalenediimide-Based Donor-Acceptor Columnar Liquid Crystals | 100 | ||
| 4.3.1 Independent Naphthalenediimide | 101 | ||
| 4.3.2 Naphthalenediimide Donor-Acceptor Columnar Liquid Crystals | 103 | ||
| 4.3.3 Thermochromic Phase Properties of NDI-DAN Materials | 105 | ||
| 4.3.4 NDI with Other Electron-Rich Naphthalene Components | 107 | ||
| 4.3.5 Predictable Absorption in Modular NDI DACLC Materials | 108 | ||
| 4.3.6 Strongly Dichroic Thin-Films in NDI-Anthracene DACLC Materials | 110 | ||
| 4.4 Conclusion | 112 | ||
| References | 113 | ||
| Chapter 5 Naphthalene-diimide (NDI) Nanofibre, Gel and Mesoscopic Material | 116 | ||
| 5.1 Introduction | 116 | ||
| 5.2 Various Mesoscopic Materials from Self-assembled NDI | 118 | ||
| 5.3 Assembly of Amphiphilic NDI | 127 | ||
| 5.4 Self-assembled Core-substituted NDI | 135 | ||
| 5.4.1 Naphthalene-diimide-based Gelators | 140 | ||
| 5.5 Conclusion | 161 | ||
| Acknowledgments | 162 | ||
| References | 162 | ||
| Chapter 6 Polymeric Materials Based on NDI and its Congeners | 167 | ||
| 6.1 Introduction | 167 | ||
| 6.1.1 The Structures of NDI-based Polymers | 167 | ||
| 6.2 Conjugated Polymers Containing NDI for Organic Electronic Devices | 168 | ||
| 6.2.1 NDI Polymers for Field-Effect Transistors | 169 | ||
| 6.2.2 NDI Polymers for Photovoltaic Devices | 179 | ||
| 6.2.3 Conclusions for NDI-based Polymers for Organic Electronic Devices | 187 | ||
| 6.3 Chemosensors Containing NDI Residues | 187 | ||
| 6.3.1 NDI Polymers for pH Sensors | 187 | ||
| 6.3.2 Fluoride Sensors from NDI-containing Polymers | 190 | ||
| 6.3.3 Conclusions for NDI-containing Chemosensors | 193 | ||
| 6.4 Self-assembled Poly-NDI Structures through Non-covalent Interactions | 193 | ||
| 6.4.1 Self-assembled Polymers Containing NDI (Acceptor) and Donor Residues in the Main Chain | 194 | ||
| 6.4.2 Self-assembled Polymers with NDI as Pendent Side Groups | 198 | ||
| 6.4.3 Self-assembled Polymers Utilising Electronically Complementary NDI-containing End Groups | 200 | ||
| 6.5 Healable Supramolecular Polymers Utilising NDI | 201 | ||
| 6.5.1 Chain-folding NDI Homopolymers | 203 | ||
| 6.5.2 Chain-folding NDI Copolymers | 205 | ||
| 6.5.3 Nanoparticle-reinforcing Chain-folding NDI Copolymers | 209 | ||
| 6.5.4 Conclusions for Healable Supramolecular Polymers | 211 | ||
| 6.6 Conclusions | 211 | ||
| References | 211 | ||
| Chapter 7 Tunable Electronic Interactions between Aromatic Diimides and Anions | 218 | ||
| 7.1 Introduction | 218 | ||
| 7.1.1 Electronic Properties and Utilities of Aromatic Diimides | 218 | ||
| 7.1.2 Importance of Anions and Anion Recognition | 219 | ||
| 7.1.3 Scope and Limitations of Traditional Anion Receptors | 220 | ||
| 7.1.4 Anion-π Interactions: A New Paradigm of Anion Recognition Chemistry\r | 220 | ||
| 7.2 Transmembrane Anion Channels Based on Rigid NDI and PDI Rods | 221 | ||
| 7.2.1 The Significance and Mechanism of Anion Channels | 221 | ||
| 7.2.2 Anion Antiport through Rigid NDI Rod-based Anion Channels | 222 | ||
| 7.2.3 Can Weak Anion-π Interactions Overcome Dehydration Penalties of Anions?\r | 225 | ||
| 7.3 Photosynthetic Activity of PDI Rods | 226 | ||
| 7.4 Tunable Noncovalent Interactions between Anions and π-acidic NDIs and PDIs\r | 228 | ||
| 7.4.1 Electronic Constraints of Donor-Acceptor ET and CT Interactions | 228 | ||
| 7.4.2 UV/Vis Spectroscopic Evidence of Anion-induced ET and CT Events | 229 | ||
| 7.4.3 Electron-donating Abilities of Anions in Aprotic Solvents | 232 | ||
| 7.4.4 NMR and EPR Evidence of Anion-induced Reduction of π-Acids\r | 233 | ||
| 7.4.5 Anion-induced Reduction and Deprotonation of NDI Derivatives | 235 | ||
| 7.4.6 Cation-induced Oxidation of Electron-rich Amino-NDI Derivatives | 235 | ||
| 7.5 Radical Reactions via Anion-induced ET to π-acidic Imides and Diimides\r | 236 | ||
| 7.6 Crystal Structures of Anion-NDI Complexes | 237 | ||
| 7.7 Conclusions and Outlook | 239 | ||
| Acknowledgments | 239 | ||
| References | 239 | ||
| Chapter 8 Naphthalene Diimide-based Photovoltaics | 244 | ||
| 8.1 Introduction | 244 | ||
| 8.1.1 Naphthalene Diimides | 245 | ||
| 8.1.2 Core-substituted NDIs | 248 | ||
| 8.2 Overview of Energy and Electron Transfer Processes | 249 | ||
| 8.2.1 Energy Transfer | 250 | ||
| 8.2.2 Electron Transfer | 253 | ||
| 8.3 Naphthalene Diimides in Donor-Acceptor Systems | 254 | ||
| 8.4 Naphthalene Diimides in Organic Photovoltaic (OPV) Systems | 259 | ||
| 8.4.1 NDIs as Small Molecule OFET Materials | 260 | ||
| 8.4.2 NDIs as OFET Materials in Polymers | 263 | ||
| 8.4.3 NDIs as Solar Cell Materials | 265 | ||
| 8.4.4 NDIs as Ambipolar Materials | 269 | ||
| 8.5 Conclusion | 272 | ||
| Reference | 272 | ||
| Chapter 9 Perylenetetracarboxylic Diimide and its Covalently-linked Molecular Arrays | 277 | ||
| 9.1 Introduction | 277 | ||
| 9.2 Modification of the Molecular Structure of PDI | 280 | ||
| 9.2.1 Introducing Substituents at N-Positions | 280 | ||
| 9.2.2 Introducing Substituents at the Bay Positions | 283 | ||
| 9.2.3 Introducing Substituents at the ortho-Positions | 288 | ||
| 9.3 Basic Properties of PDIs | 290 | ||
| 9.3.1 Structure | 290 | ||
| 9.3.2 Spectroscopic Properties | 291 | ||
| 9.3.3 Redox Properties | 293 | ||
| 9.3.4 Solubility and Aggregation | 294 | ||
| 9.4 Construction of PDI Molecular Arrays by Covalent Bonds | 297 | ||
| 9.4.1 General Concepts | 298 | ||
| 9.4.2 Cofacial Arrays of PDI | 300 | ||
| 9.4.3 Orthogonal Arrays of PDIs | 312 | ||
| 9.4.4 Linear Arrays of PDIs | 316 | ||
| 9.4.5 Cyclic or Hyperbranched Arrays of PDIs | 321 | ||
| 9.5 Outlook and Perspective | 326 | ||
| References | 328 | ||
| Subject Index | 337 |