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Polycyclic Arenes and Heteroarenes

Synthesis, Properties, and Applications
1. Aufl.

von: Qian Miao
142,99 €
Verlag:	Wiley-VCH
Format:	EPUB
Veröffentl.:	22.09.2015
ISBN/EAN:	9783527689576
Sprache:	englisch
Anzahl Seiten:	360

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Titelbeschreibung

The first book of its kind to focus on the chemistry of this promising class of molecules. Edited by an innovator in the field, who has gathered an international team of well-established experts, this is a comprehensive overview of the rapidly developing field of polycyclic (hetero)arenes, specifically highlighting on their molecular design and the latest synthetic procedures, as well as chemical and physical properties. Each chapter is dedicated to a specific compound class, the first eight covering polycyclic arenes, including both planar and non-planar conjugated molecules, while chapters nine to twelve deal with polycylic heteroarenes according to the heteroatoms, namely N, B, S and P. Important current and emergent applications in the field are also discussed, ranging from molecular sensors to electronic devices. The result is an essential reference for researchers in synthetic and physical organic chemistry, supramolecular chemistry, and materials science.

Inhaltsverzeichnis

Preface XI List of Contributors XIII Part I Polycyclic Arenes 1 1 Open-Shell Benzenoid Polycyclic Hydrocarbons 3 Soumyajit Das and JishanWu 1.1 Introduction 3 1.2 Higher Order Acenes 6 1.3 Phenalenyl-Based Diradicaloids 9 1.3.1 Bis(phenalenyl)s 10 1.3.2 Zethrenes 14 1.4 Anthenes and Periacenes 21 1.5 π-Extended p-Quinodimethane 27 1.6 Triangulene-Based Triplet Biradicals 31 1.7 Potential Applications 32 1.8 Conclusion 33 References 33 2 Planar Cyclopenta-Fused Polycyclic Arenes 37 Gabriel E. Rudebusch andMichael M. Haley 2.1 Introduction 37 2.2 Acenaphthylenes 37 2.3 Dibenzopentalenes 43 2.4 Indenofluorenes 51 2.5 Conclusions 57 Acknowledgment 58 References 58 3 Growing Buckybowl Chemistry 61 Shuhei Higashibayashi and Hidehiro Sakurai 3.1 Introduction 61 3.2 π-Extended Buckybowls 62 3.3 Chiral Buckybowl 65 3.4 Heterobuckybowl 68 3.5 Columnar Crystal Packing of Buckybowls 75 3.6 Summary and Conclusions 80 References 80 4 Polycyclic Arenes Containing Seven-Membered Carbocycles 85 Kwan Yin Cheung and QianMiao 4.1 Introduction 85 4.2 Azulene, Oligo-azulenes, and Fused Azulenes 85 4.3 Polycyclic Arenes Containing 5H-Dibenzo[a,d]cycloheptene Units 92 4.4 Cyclohepta[de]naphthalene, dicyclohepta[de,ij]naphthalene, and Their Benzannulated Derivatives 97 4.5 Curved Polycyclic Arenes Containing Highly Fused Cycloheptatriene 101 4.6 Conclusions 107 Acknowledgment 107 References 107 5 Polycyclic Arenes Containing Eight-Membered Carbocycles 111 Chun-Lin Deng, Xiao-Shui Peng, and Henry N. C.Wong 5.1 Introduction 111 5.2 [8]Annulenes 112 5.2.1 Dehydro[8]annulenes 112 5.2.2 Benzo-Fused [8]annulenes 116 5.2.3 Biphenylene-Fused [8]annulenes 119 5.3 Tetraphenylenes 122 5.3.1 Synthesis 122 5.3.1.1 Ring Opening of the Strained Four-Membered Ring of Biphenylene Derivatives 123 5.3.1.2 Transition-Metal-Mediated Oxidative Coupling 123 5.3.1.3 Cycloaddition–Deoxygenation Protocol 124 5.3.1.4 Synthesis of Enantiopure Tetraphenylenes 125 5.3.2 Properties and Potential Applications 127 5.4 [8]Circulene 133 5.5 Concluding Remarks 138 References 138 6 Cycloparaphenylenes and Carbon Nanorings 143 Shigeru Yamago, Eiichi Kayahara, and Sigma Hashimoto 6.1 Introduction 143 6.2 Early Developments 144 6.3 Strain and HOMO/LUMO Energies of CPPs 146 6.4 Synthesis of CPPs 147 6.5 Properties of CPPs 154 6.5.1 Photophysical Properties 154 6.5.2 Redox Properties of CPPs 155 6.5.3 Host–Guest Chemistry 158 6.6 Summary and Conclusions 160 References 160 7 Advances in Chemistry of Dehydrobenzoannulenes 163 Shunpei Nobusue and Yoshito Tobe 7.1 Introduction 163 7.2 Synthesis and Properties of New DBAs 164 7.2.1 Single-Ring DBAs 164 7.2.2 Multiple-Ring DBAs 166 7.3 DBAs as Graphyne and Graphdiyne Motifs 169 7.3.1 Theoretical and Synthetic Studies on Graphyne and Graphdiyne 170 7.3.2 Synthesis of Graphyne and Graphdiyne Motifs and Related Multiple DBA Systems 171 7.4 DBAs as Supramolecular Building Blocks 171 7.4.1 Crystal Engineering 172 7.4.2 3D Assemblies: Gels, Fibers, Vesicles, and Liquid Crystals 174 7.4.3 2D Self-Assembly on Surfaces and Interfaces 175 7.5 DBAs in Optoelectronic Applications 180 7.6 DBAs as Synthetic Precursors 181 7.6.1 Transannular Bond Formation Leading to Unconventional Aromatic Molecules 181 7.6.2 Strain-Assisted Cycloaddition and Biological Applications 185 7.7 Summary and Conclusions 187 References 187 8 Tetraarylethenes and Aggregation-Induced Emission 193 Zujin Zhao and Ben Zhong Tang 8.1 Introduction 193 8.2 Fundamentals 194 8.2.1 Pristine Tetraphenylethene (TPE) 194 8.2.2 Rigidified TPE Derivatives 195 8.2.3 Adducts of TPE and Planar Chromophores 200 8.2.4 Emission Color Tuning of TPE Derivatives 202 8.2.5 Complex Tetraarylethenes 204 8.3 Applications 210 8.3.1 Chemosensors 210 8.3.2 Mechanochromic Luminescent Materials 211 8.3.3 Light-Emitting Materials 213 8.4 Outlook 218 References 219 Part II Polycyclic Heteroarenes 223 9 N-Containing Polycyclic Heteroarenes 225 Arun Naibi Lakshminarayana and Chunyan Chi 9.1 Introduction 225 9.2 Linear and Extended N-Heteroarenes 226 9.2.1 N-Heteroacenes 226 9.2.1.1 History and Synthesis 226 9.2.1.2 Properties and Applications 228 9.2.2 Extended N-Heteroarenes 232 9.2.2.1 Unconventional N-Heteroacenes 232 9.2.2.2 N-Annulated Perylenes 235 9.3 Nitrogen-Rich Macrocyclic Arenes 236 9.3.1 Porphyrin and Porphyrinoids 236 9.3.1.1 Synthesis 237 9.3.1.2 General Properties 237 9.3.1.3 Diversity of Porphyrinoids 239 9.3.1.4 Applications 241 9.3.2 Phthalocyanines 242 9.3.2.1 History and Synthesis 242 9.3.2.2 General Properties and Applications 243 9.4 Miscellaneous 244 9.5 Summary and Conclusion 246 References 247 10 Boron-Containing Polycyclic Aromatics 251 David R. Levine and John D. Tovar 10.1 Introduction 251 10.2 Historical Perspective and Representative Structures 251 10.3 General Synthetic Strategies 253 10.3.1 Metalation/Ring Closure 253 10.3.2 Element–Boron Exchange (Metathesis) 254 10.3.3 Intramolecular Cascade Cyclizations 255 10.3.4 Photoisomerization/Thermal Isomerization 256 10.3.5 Oxidative and Radical Cyclizations – Toward Two-Dimensional π-Systems 257 10.3.6 Functionalization at Boron: Hydroboration Chemistry 258 10.4 Recent Developments in B-PAH Structures and Properties 259 10.4.1 Linear Ladder-Type π-Systems 259 10.4.1.1 Borole-Based PAHs 259 10.4.1.2 Borepin-Based PAHs 261 10.4.1.3 Boraacenes andTheir Congeners 262 10.4.1.4 Tetravalent Boron: B–N Coordinated and Other Zwitterionic Systems 265 10.4.2 Two-Dimensionally Fused π-Systems 267 10.4.2.1 Fundamental Impacts of Enforced Planarity in Triarylboranes 267 10.4.2.2 Fully Conjugated Two-Dimensional Materials 270 10.5 Conclusions/Outlook 272 References 273 11 S-Containing Polycyclic Heteroarenes: Thiophene-Fused and Thiadiazole-Fused Arenes as Organic Semiconductors 277 Masashi Mamada and Yoshiro Yamashita 11.1 Introduction 277 11.2 Electronic Structures of FusedThiophenes andThiadiazoles 278 11.3 p-Type Semiconductors with Fused Thiophenes 282 11.3.1 Acenothiophenes (AcTs) and Acenodithiophenes (AcDTs) 282 11.3.1.1 Overview 282 11.3.1.2 AcT and AcDT Derivatives 284 11.3.1.3 AcT and AcDT Derivatives with Trialkylsilylethynyl Groups 284 11.3.2 [n]Thienoacenes ([n]TAcs) and Related Compounds 286 11.3.2.1 Overview 286 11.3.2.2 [n]TAc Derivatives 286 11.3.3 Alternating Rings of Fused Benzene and Thiophene Molecules (ABTs) 288 11.3.3.1 Overview 288 11.3.3.2 Isoelectronic Analogs of Dibenzo[a,h]anthracene 290 11.3.3.3 Isoelectronic Analogs of Pentaphene 290 11.3.3.4 Isoelectronic Analogs of Benzo[a]tetracene 290 11.3.4 Diacene-Fused Thienothiophenes (DAcTTs) 290 11.3.4.1 Overview 290 11.3.4.2 Symmetric DAcTTs 291 11.3.4.3 Asymmetric DAcTTs 291 11.3.5 Others (2-D π-Extended Fused Thiophenes) 293 11.3.5.1 Overview 293 11.3.5.2 2-D π-Extended Fused Thiophenes 293 11.4 n-Type Semiconductors with Fused Thiophenes 293 11.4.1 Overview 293 11.4.2 n-Type Semiconductors with Fused Thiophenes 295 11.5 Thiadiazole Derivatives 297 11.5.1 Overview 297 11.5.2 Thiadiazole Derivatives for p-Type Semiconductors 298 11.5.3 Thiadiazole Derivatives for Ambipolar Semiconductors 298 11.5.4 Thiadiazole Derivatives for n-Type Semiconductors 300 11.6 Summary and Conclusions 300 References 303 12 P-Containing Heteroarenes: Synthesis, Properties, Applications 309 Monika Stolar and Thomas Baumgartner 12.1 Introduction 309 12.2 Five-Membered Ring Systems 309 12.3 Six-Membered Ring Systems 321 12.4 Seven-Membered Ring Systems 323 12.5 Other Phosphorus-Containing Diketo-Ring Systems 325 12.6 Summary and Conclusions 326 Acknowledgments 327 References 327 Index 331

Autorenportrait

Qian Miao is Associate Professor at the Department of Chemistry at the Chinese University of Hong Kong Shatin. He obtained his B.Sc. degree from the University of Science and Technology of China in 2000 and received his Ph.D. degree from Columbia University, USA, in 2005, under direction of Prof. Colin Nuckolls. He then did postdoctoral research with Prof. Fred Wudl at the University of California, Los Angeles, before he joined the Chinese University of Hong Kong as an assistant professor in 2006. He was promoted to associate professor in 2012. His research aims at the design and synthesis of functional organic materials with high performance and novel functions, and currently focuses on organic semiconductor materials and devices.

Back cover copy

Graphene, a giant molecule containing carbon atoms packed in a honeycomb lattice, is an extreme case of the compound class known as polycyclic arenes. Introduction of hetero-atoms, such as B and N, to the _-backbones of polycyclic arenes results in interesting heteroarene molecules that are structurally similar to their hydrocarbon analogues but which show different properties. Polycyclic arenes and heteroarenes play an important role in various fields such as organic electronics, medicine or energy. The editor, one of the leaders in the field, has gathered an international team of well-established experts, to provide this comprehensive overview of the rapidly developing field of polycyclic (hetero) arenes. Their molecular design and the latest synthetic procedures, as well as chemical and physical properties are specifically highlighted. Each chapter is dedicated to a specific compound class, the first eight covering polycyclic arenes, including both planar and non-planar conjugated molecules, while chapters nine to twelve deal with polycylic heteroarenes according to the heteroatoms, namely N, B, S and P. Important current and emergent applications in the field are also discussed, ranging from molecular sensors to electronic devices. The result is an essential reference for researchers in synthetic and physical organic chemistry, supra-molecular chemistry, and materials science.