{"product_id":"organic-redox-systems-isbn-9781118858745","title":"Organic Redox Systems","description":"\u003cp\u003e\u003cb\u003eProviding a thorough overview of leading research from internationally-recognized contributing authors, this book describes methods for the preparation and application of redox systems for organic electronic materials like transistors, photovoltaics, and batteries.\u003c\/b\u003e\u003c\/p\u003e \u003cul\u003e \u003cli\u003eCovers bond formation and cleavage, supramolecular systems, molecular design, and synthesis and properties\u003c\/li\u003e \u003cli\u003eAddresses preparative methods, unique structural features, physical properties, and material applications of redox active p-conjugated systems\u003c\/li\u003e \u003cli\u003eOffers a useful guide for both academic and industrial chemists involved with organic electronic materials\u003c\/li\u003e \u003cli\u003eFocuses on the transition-metal-free redox systems composed of organic and organo main group compounds\u003c\/li\u003e \u003c\/ul\u003e \u003cp\u003eLIST OF CONTRIBUTO RS xv\u003c\/p\u003e \u003cp\u003ePREFACE xix\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1 Introduction: Basic Concepts and a Brief History of Organic Redox Systems 1\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eTohru Nishinaga\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e1.1 Redox Reaction of Organic Molecules, 1\u003c\/p\u003e \u003cp\u003e1.2 Redox Potential in Nonaqueous Solvents, 3\u003c\/p\u003e \u003cp\u003e1.3 A Brief History of Organic Redox Compounds, 5\u003c\/p\u003e \u003cp\u003eReferences, 10\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Redox©\\Mediated Reversible 𝞂©\\Bond Formation\/Cleavage 13\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eTakanori Suzuki, Hitomi Tamaoki, Jun©\\ichi Nishida, Hiroki Higuchi, Tomohiro Iwai, Yusuke Ishigaki, Keisuke Hanada, Ryo Katoono, Hidetoshi Kawai, Kenshu Fujiwara and Takanori Fukushima\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e2.1 Dynamic Redox (“Dyrex”) Systems, 13\u003c\/p\u003e \u003cp\u003e2.1.1 π©\\Electron Systems Exhibiting Drastic Structural Changes upon Electron Transfer, 13\u003c\/p\u003e \u003cp\u003e2.1.2 Redox Switching of a σ©\\Bond upon Electron Transfer, 16\u003c\/p\u003e \u003cp\u003e2.1.3 Two Types of Dyrex Systems Exhibiting Redox Switching of a σ©\\Bond, 17\u003c\/p\u003e \u003cp\u003e2.2 Advanced Electrochromic Response of “Endo”©\\Type Dyrex Systems Exhibiting Redox Switching of a σ©\\Bond, 19\u003c\/p\u003e \u003cp\u003e2.2.1 Tetraaryldihydrophenanthrenes as Prototypes of “Endo”©\\Dyrex Systems, 19\u003c\/p\u003e \u003cp\u003e2.2.2 Tricolor Electrochromism with Hysteretic Color Change in Non©\\C2©\\Symmetric “Endo”©\\Dyrex Pair, 20\u003c\/p\u003e \u003cp\u003e2.2.3 Electrochromism with Chiroptical Output of Chiral “Endo”©\\Dyrex Pair, 21\u003c\/p\u003e \u003cp\u003e2.2.4 Multi©\\Output Response System Based on Electrochromic “Endo”©\\Dyrex Pair, 24\u003c\/p\u003e \u003cp\u003e2.3 Advanced Electrochromic Response of “Exo”©\\Type Dyrex Systems Exhibiting Redox Switching of a σ©\\Bond, 26\u003c\/p\u003e \u003cp\u003e2.3.1 Bis(diarylethenyl)biphenyls as Prototypes of “Exo”©\\Dyrex Systems, 26\u003c\/p\u003e \u003cp\u003e2.3.2 Electrochromism with Chiroptical Output of Chiral “Exo”©\\Dyrex Systems, 26\u003c\/p\u003e \u003cp\u003e2.3.3 Electrochromism of “Exo”©\\Dyrex Systems in Aqueous Media, 28\u003c\/p\u003e \u003cp\u003e2.4 Prospect: Redox Systems With Multiple Dyrex Units, 31\u003c\/p\u003e \u003cp\u003eReferences, 33\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Redox©\\Controlled Intramolecular Motions Triggered by π©\\Dimerization and Pimerization Processes 39\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eChristophe Kahlfuss, Eric Saint©\\Aman and Christophe Bucher\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e3.1 Introduction, 39\u003c\/p\u003e \u003cp\u003e3.2 Oligothiophenes, 40\u003c\/p\u003e \u003cp\u003e3.3 Phenothiazine, 44\u003c\/p\u003e \u003cp\u003e3.4 Naphthalene and Perylene Bisimides, 45\u003c\/p\u003e \u003cp\u003e3.5 para©\\Phenylenediamine, 47\u003c\/p\u003e \u003cp\u003e3.6 Pyridinyl Radicals, 49\u003c\/p\u003e \u003cp\u003e3.7 Viologen Derivatives, 50\u003c\/p\u003e \u003cp\u003e3.8 Verdazyl, 60\u003c\/p\u003e \u003cp\u003e3.9 Phenalenyl, 60\u003c\/p\u003e \u003cp\u003e3.10 Porphyrins, 61\u003c\/p\u003e \u003cp\u003e3.11 Benzenoid, 62\u003c\/p\u003e \u003cp\u003e3.12 Cyclophane, 64\u003c\/p\u003e \u003cp\u003e3.13 Tetrathiafulvalene, 68\u003c\/p\u003e \u003cp\u003e3.14 Conclusion, 80\u003c\/p\u003e \u003cp\u003eAcknowledgments, 80\u003c\/p\u003e \u003cp\u003eReferences, 81\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Tetrathiafulvalene: a Redox Unit for Functional Materials and a Building Block for Supramolecular Self©\\Assembly 89\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMasashi Hasegawa and Masahiko Iyoda\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e4.1 Introduction: Past and Present of TTF Chemistry, 89\u003c\/p\u003e \u003cp\u003e4.2 Basic Redox Properties of TTF and Stacked TTF, 90\u003c\/p\u003e \u003cp\u003e4.2.1 Monomeric TTFs, 90\u003c\/p\u003e \u003cp\u003e4.2.2 Interactions in Stacked TTF Dimer, 92\u003c\/p\u003e \u003cp\u003e4.2.3 Interactions in Stacked TTF Oligomers, 97\u003c\/p\u003e \u003cp\u003e4.2.4 Head©\\to©\\Tail TTF Dimer, 98\u003c\/p\u003e \u003cp\u003e4.3 TTF as a Faithful Redox Active Unit in Functional Materials, 100\u003c\/p\u003e \u003cp\u003e4.3.1 Electrochromic Materials, 100\u003c\/p\u003e \u003cp\u003e4.3.2 Optically Active TTFs, 102\u003c\/p\u003e \u003cp\u003e4.3.3 Uses as Positive Electrode Materials for Rechargeable Batteries, 108\u003c\/p\u003e \u003cp\u003e4.4 Electroconducting Properties of TTF Derivatives Based on Supramolecular Self©\\Assembly, 112\u003c\/p\u003e \u003cp\u003e4.4.1 Redox©\\Active Nanostructure Formation in the Solid State, 113\u003c\/p\u003e \u003cp\u003e4.4.2 Conducting Nanostructure Formation, 115\u003c\/p\u003e \u003cp\u003e4.4.3 Conducting Nanofibers by Iodine Doping, 116\u003c\/p\u003e \u003cp\u003e4.4.4 Conducting Nanofibers Based on Cation Radicals, 120\u003c\/p\u003e \u003cp\u003e4.4.5 Conducting Nanowires of Neutral TTF Derivatives, 123\u003c\/p\u003e \u003cp\u003e4.5 Summary and Outlook, 124\u003c\/p\u003e \u003cp\u003eReferences, 125\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Robust Aromatic Cation Radicals as Redox Tunable Oxidants 131\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMarat R. Talipov and Rajendra Rathore\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction, 131\u003c\/p\u003e \u003cp\u003e5.2 Designing Molecules for the Formation of Stable Cation Radicals (Crs)—A Case Study, 135\u003c\/p\u003e \u003cp\u003e5.2.1 Exploring the Cause of Exceptional Stability of The©\\Orange+·, 137\u003c\/p\u003e \u003cp\u003e5.3 Methods of Preparative Isolation of Aromatic Cation Radicals, 142\u003c\/p\u003e \u003cp\u003e5.3.1 Nitrosonium (NO+) Salts, 143\u003c\/p\u003e \u003cp\u003e5.3.2 Antimony Pentachloride (SbCl5), 144\u003c\/p\u003e \u003cp\u003e5.3.3 Triethyloxonium Hexachloroantimonate (Et3O+ SbCl6 –), 148\u003c\/p\u003e \u003cp\u003e5.3.4 Ddq and HBF4©\\Ether Complex, 149\u003c\/p\u003e \u003cp\u003e5.4 Q uantitative Oxidation of Electron Donors using THE-Orange+·SbCl6 – as One©\\Electron Oxidant, 150\u003c\/p\u003e \u003cp\u003e5.4.1 Analysis of Two©\\Electron Oxidation Processes Using MF\/D Plots, 157\u003c\/p\u003e \u003cp\u003e5.5 Readily Available Electron Donors for the Redox©\\Tunable Aromatic Oxidants, 164\u003c\/p\u003e \u003cp\u003e5.5.1 Triptycene Based Electron Donors, 164\u003c\/p\u003e \u003cp\u003e5.5.2 Tetrabenzodifurans, 166\u003c\/p\u003e \u003cp\u003e5.5.3 Polyaromatic Hydrocarbons, 168\u003c\/p\u003e \u003cp\u003e5.5.4 Multi©\\Electron Redox Systems, 168\u003c\/p\u003e \u003cp\u003e5.6 Conclusion, 171\u003c\/p\u003e \u003cp\u003eReferences, 173\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 Air©\\Stable Redox©\\Active Neutral Radicals: Topological Symmetry Control of Electronic©\\Spin, Multicentered Chemical Bonding, and Organic Battery Application 177\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eShinsuke Nishida and Yasushi Morita\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e6.1 Introduction, 177\u003c\/p\u003e \u003cp\u003e6.2 Open©\\Shell Graphene Fragment : Design and Synthesis of Air©\\Stable Carbon©\\Centered Neutral Radicals Based on Fused©\\Polycyclic π©\\System, 179\u003c\/p\u003e \u003cp\u003e6.3 Topological Symmetry Control of Electronic©\\Spin Density Distribution by Redox and other External Stimuli, 181\u003c\/p\u003e \u003cp\u003e6.3.1 Redox©\\Based Spin Diversity of Oxophenalenoxyl Sytems, 181\u003c\/p\u003e \u003cp\u003e6.3.2 Spin©\\Center Transfer and Solvato©\\\/Thermochromism of Tetrathiafulvalene©\\Substituted 6©\\Oxophenalenoxyl Neutral Radical, 183\u003c\/p\u003e \u003cp\u003e6.4 Control of Electronic©\\Spin Structure and Optical Properties of Multicentered C©¤C Bonds, 184\u003c\/p\u003e \u003cp\u003e6.4.1 Strong Somo–Somo Interaction within π©\\Dimeric Structure of Phenalenyl Derivatives, 184\u003c\/p\u003e \u003cp\u003e6.4.2 Thermochromism Induced by Thermal Equilibrium of π©\\Dimeric Structure and σ©\\Dimeric Structure, 188\u003c\/p\u003e \u003cp\u003e6.4.3 Weak Somo–Somo Interactions by Molecular Modification of Phenalenyl System, 190\u003c\/p\u003e \u003cp\u003e6.4.4 Multidimensional Spin–Spin Interaction and π©\\Staked Radical Polymer, 193\u003c\/p\u003e \u003cp\u003e6.5 Rechargeable Batteries Using Organic Electrode©\\Active Materials, 195\u003c\/p\u003e \u003cp\u003e6.5.1 Closed©\\Shell Organic Molecules as Electrode©\\Active Materials, 196\u003c\/p\u003e \u003cp\u003e6.5.2 Closed©\\Shell Organic Polymers, 214\u003c\/p\u003e \u003cp\u003e6.5.3 Stable Organic Neutral Radicals, 218\u003c\/p\u003e \u003cp\u003e6.5.4 Stable Organic Neutral Radical Polymers, 220\u003c\/p\u003e \u003cp\u003e6.6 Molecular Spin Batteries : Design Criteria and Performance of High Capacity Organic Rechargeable Battery Materials, 223\u003c\/p\u003e \u003cp\u003e6.6.1 Molecular Crystalline Secondary Batteries, 223\u003c\/p\u003e \u003cp\u003e6.6.2 Trioxotriangulene Neutral Radical (Tot) Derivatives, 224\u003c\/p\u003e \u003cp\u003e6.6.3 Molecular Spin Batteries, 227\u003c\/p\u003e \u003cp\u003e6.7 Conclusion, 229\u003c\/p\u003e \u003cp\u003eAcknowledgement, 231\u003c\/p\u003e \u003cp\u003eReferences, 231\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Triarylamine©\\Based Organic Mixed©\\Valence Compounds: The Role of the Bridge 245\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eChristoph Lambert\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e7.1 Introduction, 245\u003c\/p\u003e \u003cp\u003e7.2 The Mv Concept, 246\u003c\/p\u003e \u003cp\u003e7.3 The Redox Center, 250\u003c\/p\u003e \u003cp\u003e7.4 The Bridge, 251\u003c\/p\u003e \u003cp\u003e7.5 The Length of the Bridge, 254\u003c\/p\u003e \u003cp\u003e7.6 Changing the Connectivity, 256\u003c\/p\u003e \u003cp\u003e7.7 Twisting the Bridge, 258\u003c\/p\u003e \u003cp\u003e7.8 Saturated vs Unsaturated Bridge, 258\u003c\/p\u003e \u003cp\u003e7.9 Meta vs Para Conjugation, 260\u003c\/p\u003e \u003cp\u003e7.10 Switching the Bridge, 262\u003c\/p\u003e \u003cp\u003e7.11 Metal Atoms as the Bridge, 263\u003c\/p\u003e \u003cp\u003e7.12 And Finally: Without a Bridge, 264\u003c\/p\u003e \u003cp\u003eAcknowledgment, 265\u003c\/p\u003e \u003cp\u003eReferences, 265\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Magnetic Properties of Multiradicals Based on Triarylamine Radical Cations 269\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eShuichi Suzuki and Keiji Okada\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e8.1 Introduction, 269\u003c\/p\u003e \u003cp\u003e8.2 Triarylamine Radical Cations as Synthetic Reagents for Preparation of Donor Radical Cations with Various Counter Anions, 270\u003c\/p\u003e \u003cp\u003e8.2.1 Syntheses of Tbpa +·Pf6− and Its Counteranion Analogues, 270\u003c\/p\u003e \u003cp\u003e8.3 Stable Triarylamines without para©\\Substituents, 270\u003c\/p\u003e \u003cp\u003e8.4 Models of Intermolecular Exchange Interaction in Heteroatomic Systems, 271\u003c\/p\u003e \u003cp\u003e8.4.1 Dynamic Spin Polarization Model and Disjoint–Nondisjoint Model, 271\u003c\/p\u003e \u003cp\u003e8.4.2 Dynamic Spin Polarization and Spin Delocalization, 272\u003c\/p\u003e \u003cp\u003e8.4.3 Effect of Large Dihedral Angle between Spacer and Spin Source, 273\u003c\/p\u003e \u003cp\u003e8.4.4 p©\\Phenylene Methodology or π©\\Conjugation Using Topologically Different Spin Sources, 275\u003c\/p\u003e \u003cp\u003e8.5 Magnetic Susceptibility and Temperature Dependence, 275\u003c\/p\u003e \u003cp\u003e8.6 Poly(Diarylamino benzene) Poly(Radical Cation)s, 276\u003c\/p\u003e \u003cp\u003e8.7 Radical Substituted Triarylamines, 278\u003c\/p\u003e \u003cp\u003e8.7.1 tbuno©\\Substituted Triarylamines, 278\u003c\/p\u003e \u003cp\u003e8.7.2 Nn©\\Substituted Triarylamines, 279\u003c\/p\u003e \u003cp\u003e8.8 Towards Further Developments, 282\u003c\/p\u003e \u003cp\u003eReferences, 283\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 Open©\\Shell π©\\Conjugated Hydrocarbons 287\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eTakashi Kubo\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e9.1 Introduction, 287\u003c\/p\u003e \u003cp\u003e9.2 Monoradicals, 288\u003c\/p\u003e \u003cp\u003e9.2.1 Triphenylmethyl, 288\u003c\/p\u003e \u003cp\u003e9.2.2 Phenalenyl, 289\u003c\/p\u003e \u003cp\u003e9.2.3 Cyclopentadienyl, Indenyl, Fluorenyl, 291\u003c\/p\u003e \u003cp\u003e9.2.4 Cycloheptatrienyl, 293\u003c\/p\u003e \u003cp\u003e9.2.5 Bdpa , 294\u003c\/p\u003e \u003cp\u003e9.2.6 Dinaphthofluorenyl, 294\u003c\/p\u003e \u003cp\u003e9.3 Biradicals, 295\u003c\/p\u003e \u003cp\u003e9.3.1 Triplet Biradicals, 295\u003c\/p\u003e \u003cp\u003e9.3.2 Singlet Biradicals: Quinodimethanes, 296\u003c\/p\u003e \u003cp\u003e9.3.3 Singlet Biradicals: Bisphenalenyl System, 298\u003c\/p\u003e \u003cp\u003e9.3.4 Singlet Biradicals: Acences, 300\u003c\/p\u003e \u003cp\u003e9.3.5 Singlet Biradicals: Anthenes, 301\u003c\/p\u003e \u003cp\u003e9.3.6 Singlet Biradicals: Zethrenes, 303\u003c\/p\u003e \u003cp\u003e9.3.7 Singlet Biradicals: Indenofluorenes, 304\u003c\/p\u003e \u003cp\u003e9.4 Polyradicals, 304\u003c\/p\u003e \u003cp\u003eReferences, 305\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 Indenofluorenes and Related Structures 311\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eJonathan L. Marshall and Michael M. Haley\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e10.1 Introduction, 311\u003c\/p\u003e \u003cp\u003e10.2 Indeno[1,2©\\a]fluorenes, 313\u003c\/p\u003e \u003cp\u003e10.2.1 Indeno[1,2©\\a]fluorene©\\7,12©\\dione, 313\u003c\/p\u003e \u003cp\u003e10.2.2 Truxenone, An Indeno[1,2©\\a]fluorene Related Structure, 314\u003c\/p\u003e \u003cp\u003e10.3 Indeno[1,2©\\b]fluorenes, 320\u003c\/p\u003e \u003cp\u003e10.3.1 Indeno[1,2©\\b]fluorene©\\6,12©\\diones, 320\u003c\/p\u003e \u003cp\u003e10.3.2 Dicyanomethylene Indeno[1,2©\\b]fluorenes, 325\u003c\/p\u003e \u003cp\u003e10.3.3 Fully Conjugated Indeno[1,2©\\b]fluorenes, 327\u003c\/p\u003e \u003cp\u003e10.4 Indeno[2,1©\\a]fluorenes, 333\u003c\/p\u003e \u003cp\u003e10.5 Indeno[2,1©\\b]fluorenes, 336\u003c\/p\u003e \u003cp\u003e10.6 Indeno[2,1©\\c]fluorenes, 339\u003c\/p\u003e \u003cp\u003e10.6.1 Indenofluorene-Related Structures, 341\u003c\/p\u003e \u003cp\u003e10.7 Fluoreno[4,3©\\c]fluorene, 342\u003c\/p\u003e \u003cp\u003e10.8 Indacenedithiophenes, 345\u003c\/p\u003e \u003cp\u003e10.8.1 Indacenedithiophene Diones, 345\u003c\/p\u003e \u003cp\u003e10.8.2 Tetrathiofulvalene and Dicyanomethylene Indacenedithiophenes, 347\u003c\/p\u003e \u003cp\u003e10.8.3 Fully Conjugated Indacenedithiophenes, 349\u003c\/p\u003e \u003cp\u003e10.9 Diindeno[n]thiophenes, 351\u003c\/p\u003e \u003cp\u003e10.10 Conclusions, 354\u003c\/p\u003e \u003cp\u003eAcknowledgment, 354\u003c\/p\u003e \u003cp\u003eReferences, 354\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 Thienoacenes 359\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eKazuo Takimiya\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e11.1 Introduction, 359\u003c\/p\u003e \u003cp\u003e11.2 Synthesis of Thienoacenes via Thienannulation, 361\u003c\/p\u003e \u003cp\u003e11.2.1 Bdt and Adt Derivatives, 361\u003c\/p\u003e \u003cp\u003e11.2.2 Thienannulation to Construct Thienoacenes with Terminal Thiophene Ring(s), 362\u003c\/p\u003e \u003cp\u003e11.2.3 Thienannulation to Construct Thienoacenes with Internal Thiophene Ring(s), 366\u003c\/p\u003e \u003cp\u003e11.3 Molecular Electronic Structures, 370\u003c\/p\u003e \u003cp\u003e11.4 Application to Electronic Devices, 373\u003c\/p\u003e \u003cp\u003e11.4.1 Molecular Organic Semiconductors for p©\\Type OFET Devices, 373\u003c\/p\u003e \u003cp\u003e11.4.2 Semiconducting Polymers for Pscs, 377\u003c\/p\u003e \u003cp\u003e11.5 Summary, 379\u003c\/p\u003e \u003cp\u003eReferences, 379\u003c\/p\u003e \u003cp\u003e\u003cb\u003e12 Cationic Oligothiophenes: p©\\Doped Polythiophene Models and Applications 383\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eTohru Nishinaga\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e12.1 Introduction, 383\u003c\/p\u003e \u003cp\u003e12.2 Design Principle and Synthetic Methods, 384\u003c\/p\u003e \u003cp\u003e12.3 Electrochemistry, 390\u003c\/p\u003e \u003cp\u003e12.4 Structural and Spectroscopic Properties as p©\\Doped Polythiophene Models, 397\u003c\/p\u003e \u003cp\u003e12.5 Application to Supramolecular Systems, 403\u003c\/p\u003e \u003cp\u003e12.6 Conclusion and Outlook, 406\u003c\/p\u003e \u003cp\u003eReferences, 406\u003c\/p\u003e \u003cp\u003e\u003cb\u003e13 Electron©\\Deficient Conjugated Heteroaromatics 411\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eYutaka Ie and Yoshio Aso\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e13.1 Introduction, 411\u003c\/p\u003e \u003cp\u003e13.2 Hexafluorocyclopenta[c]thiophene and its Containing Oligothiiophenes, 412\u003c\/p\u003e \u003cp\u003e13.3 Difluoromethylene©\\Bridged Bithiophene and its Containing Oligothiiophenes, 416\u003c\/p\u003e \u003cp\u003e13.4 π©\\Conjugated Systems Having Thiazole©\\Based Carbonyl©\\Bridged Compounds, 419\u003c\/p\u003e \u003cp\u003e13.5 Difluorodioxocyclopentene©\\Annelated Thiophene and its Containing Oligothiiophenes, 427\u003c\/p\u003e \u003cp\u003e13.6 Dioxocycloalkene©\\Annelated Thiophene and its Containing Oligothiiophenes, 433\u003c\/p\u003e \u003cp\u003e13.7 Dicyanomethylene©\\Substituted Cyclopenta[b]thiophene and its Containing π©\\Conjugated System, 434\u003c\/p\u003e \u003cp\u003e13.8 Electron©\\Deficient π©\\Conjugated System Containing Dicyanomethylene©\\Substituted Cyclopenta[b]thiophene Toward Organic Photovoltaics, 437\u003c\/p\u003e \u003cp\u003e13.9 Conclusion, 440\u003c\/p\u003e \u003cp\u003eReferences, 441\u003c\/p\u003e \u003cp\u003e\u003cb\u003e14 Oligofurans 445\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eOri Gidron\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e14.1 Background, 445\u003c\/p\u003e \u003cp\u003e14.2 Synthesis and Reactivity, 446\u003c\/p\u003e \u003cp\u003e14.3 Properties of Oligofurans in the Neutral State, 449\u003c\/p\u003e \u003cp\u003e14.4 Properties of Cationic Oligofurans, 452\u003c\/p\u003e \u003cp\u003e14.5 Polyfurans, 454\u003c\/p\u003e \u003cp\u003e14.6 Devices with Furan©\\Containing Materials, 455\u003c\/p\u003e \u003cp\u003e14.7 Summary and Outlook, 459\u003c\/p\u003e \u003cp\u003eReferences, 459\u003c\/p\u003e \u003cp\u003e\u003cb\u003e15 Oligopyrroles and Related Compounds 463\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMasayoshi Takase\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e15.1 Introduction, 463\u003c\/p\u003e \u003cp\u003e15.2 Linear Oligopyrroles, 464\u003c\/p\u003e \u003cp\u003e15.2.1 Synthesis, 464\u003c\/p\u003e \u003cp\u003e15.2.2 Optical and Redox Properties, 465\u003c\/p\u003e \u003cp\u003e15.2.3 π©\\Dimer of Oligopyrrole Radical Cations, 466\u003c\/p\u003e \u003cp\u003e15.3 Cyclic Oligopyrroles, 467\u003c\/p\u003e \u003cp\u003e15.3.1 Synthesis, 468\u003c\/p\u003e \u003cp\u003e15.3.2 Optical and Redox Properties, 469\u003c\/p\u003e \u003cp\u003e15.4 Pyrrole©\\Fused Azacoronenes, 469\u003c\/p\u003e \u003cp\u003e15.4.1 Synthesis, 470\u003c\/p\u003e \u003cp\u003e15.4.2 Optical and Redox Properties, 470\u003c\/p\u003e \u003cp\u003e15.4.3 Aromaticity, 473\u003c\/p\u003e \u003cp\u003e15.5 Conclusions, 474\u003c\/p\u003e \u003cp\u003eReferences, 474\u003c\/p\u003e \u003cp\u003e\u003cb\u003e16 Phospholes and Related Compounds: Syntheses, Redox Properties, and Applications to Organic Electronic Devices 477\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eYoshihiro Matano\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e16.1 Introduction, 477\u003c\/p\u003e \u003cp\u003e16.2 Synthesis of π©\\Conjugated Phosphole Derivatives, 478\u003c\/p\u003e \u003cp\u003e16.3 Redox Potentials of Phosphole Derivatives, 483\u003c\/p\u003e \u003cp\u003e16.4 Electrochemical Behaviors of Phosphole Derivatives, 493\u003c\/p\u003e \u003cp\u003e16.5 Applications of Phosphole©\\Based Materials to Organic Electronic Devices, 495\u003c\/p\u003e \u003cp\u003eReferences, 497\u003c\/p\u003e \u003cp\u003e\u003cb\u003e17 Electrochemical Behavior and Redox Chemistry of Boroles 503\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eHolger Braunschweig and Ivo Krummenacher\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e17.1 Introduction, 503\u003c\/p\u003e \u003cp\u003e17.2 Preparation, 505\u003c\/p\u003e \u003cp\u003e17.3 Chemical Reactivity, 507\u003c\/p\u003e \u003cp\u003e17.3.1 Lewis Acid–Base Adducts, 507\u003c\/p\u003e \u003cp\u003e17.3.2 Cycloaddition Reactions, 508\u003c\/p\u003e \u003cp\u003e17.3.3 σ©\\Bond Activation Reactions, 509\u003c\/p\u003e \u003cp\u003e17.4 Redox Chemistry, 510\u003c\/p\u003e \u003cp\u003e17.4.1 Electrochemistry, 510\u003c\/p\u003e \u003cp\u003e17.4.2 Preparative Reduction Chemistry, 514\u003c\/p\u003e \u003cp\u003e17.5 Conclusions and Outlook, 518\u003c\/p\u003e \u003cp\u003eReferences, 519\u003c\/p\u003e \u003cp\u003e\u003cb\u003e18 Isolation and Crystallization of Radical Cations by Weakly Coordinating Anions 523\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eXinping Wang\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e18.1 Introduction, 523\u003c\/p\u003e \u003cp\u003e18.2 Radical Cations and Dications Based on Triarylamines, 524\u003c\/p\u003e \u003cp\u003e18.3 Radical Cations Containing Phosphorus, 528\u003c\/p\u003e \u003cp\u003e18.4 The Radical Cation Containing a Selenium–Selenium Three©\\Electron σ©\\Bond, 534\u003c\/p\u003e \u003cp\u003e18.5 Radical Cations of Organic Oligomers (π©\\Dimerization), 536\u003c\/p\u003e \u003cp\u003e18.6 σ©\\Dimerization of Radical Cations, 540\u003c\/p\u003e \u003cp\u003e18.7 Conclusion, 541\u003c\/p\u003e \u003cp\u003eReferences, 542\u003c\/p\u003e \u003cp\u003e\u003cb\u003e19 Heavier Group 14 Element Redox Systems 545\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eVladimir Ya. Lee and Akira Sekiguchi\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e19.1 Introduction, 545\u003c\/p\u003e \u003cp\u003e19.2 Redox Systems of the Heavier Group 14 Elements E (E = Si–Pb), 547\u003c\/p\u003e \u003cp\u003e19.2.1 Interconversion between Cations R3E+, Radicals R3E ·, and Anions R3E−, 547\u003c\/p\u003e \u003cp\u003e19.2.2 Anion and Cation©\\Radicals of the Heavy Analogs of Carbenes R2E:, 552\u003c\/p\u003e \u003cp\u003e19.2.3 Anion©\\ and Cation©\\Radicals of the Heavy Analogs of Alkenes R2E¨TER2 and Heavy Analogs of Alkynes R©¤E≡E©¤R, 555\u003c\/p\u003e \u003cp\u003e19.3 Summary, 559\u003c\/p\u003e \u003cp\u003eReferences, 559\u003c\/p\u003e \u003cp\u003e\u003cb\u003e20 π©\\Electron Redox Systems of Heavier Group 15 Elements 563\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eTakahiro Sasamori, Norihiro Tokitoh and Rainer Streubel\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e20.1 Introduction, 563\u003c\/p\u003e \u003cp\u003e20.2 The Redox Behavior of Dipnictenes, 564\u003c\/p\u003e \u003cp\u003e20.3 The Redox Behavior of π©\\Conjugated Systems of Heavier Dipnictenes, 571\u003c\/p\u003e \u003cp\u003e20.4 The Redox Behavior of d–π Electron Systems Containing Heavier Dipnictenes, 572\u003c\/p\u003e \u003cp\u003e20.5 Conclusion, 575\u003c\/p\u003e \u003cp\u003eReferences, 575\u003c\/p\u003e \u003cp\u003eIndex 579\u003c\/p\u003e \u003cp\u003e\u003cb\u003eTohru Nishinaga, PhD,\u003c\/b\u003e is an Associate Professor of Chemistry at Tokyo Metropolitan University. His current research interest is the design, synthesis and application of pi-electron systems with novel electronic properties. Dr. Nishinaga has published over 80 scientific papers and 10 book chapters.\u003c\/p\u003e \u003cp\u003eRedox (reduction-oxidation) reactions include all chemical reactions in which atoms have their oxidation state changed — that is, redox reactions involve the transfer of electrons between species. The design of new redox active conjugated systems is essential for developing organic functional materials and has been the subject of intense research in recent years.\u003c\/p\u003e \u003cp\u003eProviding a thorough overview of leading research from internationally-recognized contributing authors, \u003ci\u003eOrganic Redox Systems\u003c\/i\u003e offers a valuable guide for chemists whose work touches on design and synthesis of these conjugated systems. The book covers preparative methods, unique structural features, physical properties, material applications, and potential of redox active pi-conjugated systems. Such a fundamental understanding of the structure-property relationship of these systems is one of the important research fields in physical organic chemistry. It features coverage of bond formation and cleavage of radicals, supramolecular systems based on redox reactions, molecular design, synthesis and properties, and device applications that include transistors, photovoltaics, and batteries.\u003c\/p\u003e \u003cp\u003eChemists relying on this book will find a valuable resource for research across organic and materials chemistry, with key chapters that include such topics as:\u003c\/p\u003e \u003cul\u003e \u003cli\u003eBond formation and cleavage and supramolecular assembly of radicals\u003c\/li\u003e \u003cli\u003eOxidant, mixed valence systems, and multi radicals\u003c\/li\u003e \u003cli\u003ePolycyclic aromatic hydrocarbons and heteroles\u003c\/li\u003e \u003cli\u003eWeakly coordinating anions and pi-systems of heavier group 14 and 15 elements\u003c\/li\u003e \u003c\/ul\u003e","brand":"Wiley","offers":[{"title":"Default Title","offer_id":47989732671717,"sku":"NP9781118858745","price":218.95,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/1842\/7735\/files\/9781118858745.jpg?v=1761785289","url":"https:\/\/k12savings.com\/es\/products\/organic-redox-systems-isbn-9781118858745","provider":"K12savings","version":"1.0","type":"link"}