Handbook of thiophene-based materials : applications in organic electronics and photonics (2009)

Foreword by Professor Fred Wudl Preface List of Contributors Volume One: Synthesis and Theory 1 Functional oligothiophene-based materials: nanoarchitectures and applications Amaresh Mishra, Chang-Qi Ma, Jose L. Segura and Peter Bauerle 1.1 Introduction 1.2 Functionalized oligothiophenes 1.3 Fused thiophenes 1.4 Macrocyclic thiophenes 1.5 Dendritic and hyperbranched oligothiophenes 1.6 Conclusions and prospects Acknowledgments References 2 Synthesis, characterization and properties of regioregular polythiophene-based materials Paul C. Ewbank, Mihaela C. Stefan, Genevieve Sauve and Richard D. McCullough 2.1 Introduction 2.2 Consequences of regiochemistry 2.3 Synthesis of regioregular polythiophenes 2.4 Purification and fractionation 2.5 Molecular characterization 2.6 Solid-state studies 2.7 Block copolymers containing regioregular polythiophenes 2.8 Conclusions References 3 Fused oligothiophenes Peter J. Skabara 3.1 Introduction 3.2 Synthesis and molecular properties of fused oligothiophenes 3.3 Conclusion References 4 Thiophene- S , S -dioxides as a class of electron-deficient materials for electronics and photonics Giovanna Barbarella and Manuela Melucci 4.1 Introduction 4.2 Electrochemical and photoluminescence properties 4.3 Application in devices 4.4 Conclusion Acknowledgments References 5 Synthesis and properties of oligo- and polythiophenes containing transition metals Michael O. Wolf 5.1 Introduction 5.2 Transition metal-containing oligothiophenes 5.3 Electropolymerization and properties of polymers 5.4 Conclusion and outlook References 6 Selenophenes as hetero-analogues of thiophene-based materials Tetsuo Otsubo and Kazuo Takimiya 6.1 Introduction 6.2 Selenophene-based conducting materials 6.3 Selenophene-based electroactive materials 6.4 Selenophene-based OFET materials 6.5 Conclusion References 7 Energy gaps and their control in thiophene-based polymers and oligomers Miklos Kertesz, Shujiang Yang and Yonghui Tian 7.1 Introduction 7.2 Oligomer vs PBC calculations of the bandgap 7.3 Gap and connectivity 7.4 Bandgap affected by an aromatic vs quinonoid valence tautomerism 7.5 Is a small bandgap thiophene polymer attainable? 7.6 Gaps of ladder-like PThs 7.7 Substitutions and other factors influencing the gap 7.8 Conclusion Acknowledgment References 8 Theoretical studies on thiophene-containing compounds Sanjio S. Zade and Michael Bendikov 8.1 Introduction 8.2 HOMO-LUMO gap and bandgap calculations 8.3 Nature of charge carriers 8.4 Effect of substitutions on different properties 8.5 Twisting (inter-ring deviation from planarity) in oligo- and polythiophene 8.6 IR and Raman spectra 8.7 UV-Vis spectra 8.8 Quinoid oligothiophene 8.9 Cyclic oligothiophene 8.10 New compounds with tailor-made properties 8.11 Conclusion Acknowledgments References Volume Two: Properties and Applications 9 Electrochemistry of oligothiophenes and polythiophenes Philippe Blanchard, Antonio Cravino and Eric Levillain 9.1 Introduction 9.2 Electrochemistry 9.3 Spectroelectrochemistry 9.4 Conclusion References 10 Novel photonic responses from low-dimensional crystals of thiophene/phenylene oligomers Hisao Yanagi, Fumio Sasaki, Shunsuke Kobayashi and Shu Hotta 10.1 Introduction 10.2 Low-dimensional crystals of thiophene/phenylene co-oligomers 10.3 Amplified spontaneous emission 10.4 Stimulated resonance Raman scattering 10.5 Pulse-shaped emission with time delay 10.6 Conclusion Acknowledgments References 11 Novel electronic and photonic properties of thiophene-based oligomers Shu Hotta 11.1 Introduction 11.2 Materials and molecular alignments: thin films and crystals 11.3 Charge transport: FET device applications 11.4 Photonic features: laser oscillation 11.5 Implications of the optoelectronic data of the crystals 11.6 Conclusion and future prospects Acknowledgments References 12 Liquid crystalline and electroresponsive polythiophenes Kazuo Akagi 12.1 Introduction 12.2 Synthesis and properties of LC polythiophene derivatives 12.3 FLC Polythiophene derivatives Acknowledgments References 13 Self-assembly of thiophene-based materials: a scanning tunneling microscopy perspective Clara Santato, Fabio Cicoira and Federico Rosei 13.1 Introduction 13.2 STM studies of thiophene-based materials 13.3 Conclusions and perspectives References 14 PEDOT - properties and technical relevance Knud Reuter, Stephan Kirchmeyer and Andreas Elschner 14.1 Introduction 14.2 Synthesis 14.3 Properties 14.4 Processing 14.5 Uses 14.6 Conclusion Acknowledgments References 15 Polythiophenes as active electrode materials for electrochemical capacitors Daniel Belanger 15.1 Introduction 15.2 Electrochemical capacitors 15.3 Polythiophene derivatives 15.4 Types of electrochemical capacitors 15.5 Performance and prototypes 15.6 Conclusion Acknowledgments References 16 Electroactive oligothiophenes and polythiophenes for organic field effect transistors Antonio Facchetti 16.1 Introduction 16.2 Field effect transistors 16.3 Thiophene-based oligomers for OFETs 16.4 Thiophene-based polymers for OFETs 16.5 Conclusions and outlook References 17 Thienothiophene-containing polymers for field effect transistor applications Iain McCulloch and Martin Heeney 17.1 Introduction to organic electronics 17.2 Organic field effect transistors 17.3 Organic semiconductors 17.4 Thienothiophene polymers 17.5 Conclusion References 18 Photovoltaics based on thiophene polymers: a short overview Suren A. Gevorgyan and Frederik C. Krebs 18.1 Introduction 18.2 Processing at higher levels 18.3 Thermal processing to alter morphology 18.4 Solvent vapor treatment to alter morphology 18.5 Thermocleavage 18.6 Other methods to control morphology 18.7 Conclusion Acknowledgments References 19 T hiophene-based materials for electroluminescent applications Igor F. Perepichka, Dmitrii F. Perepichka and Hong Meng 19.1 Introduction 19.2 General synthetic routes to PTs 19.3 Thiophene homopolymers 19.4 Thiophene oligomers 19.5 Copolymers of thiophenes with other conjugated moieties 19.6 Oligomers and polymers with thiophene- S , S -dioxide moiety 19.7 Thiophene materials for unconventional and advanced electroluminescent applications 19.8 Conclusions Abbreviations References 20 Thiophene-based electrochromic materials Muge Acik, Michael A. Invernale and Gregory A. Sotzing 20.1 Electrochromism and electrochromics 20.2 Electrochromism in polythiophene derivatives 20.3 Organic versus inorganic 20.4 Electrochromics in applications 20.5 Conclusion References 21 Photoresponsive thiophene-based molecules and materials Luc Ubaghs, David Sud and Neil R. Branda 21.1 Introduction 21.2 Photochromism in single crystals 21.3 Photochromism in amorphous films 21.4 Photochromism in polymers 21.5 Photochromism on metal surfaces 21.6 New architectures 21.7 Conclusion References 22 Chemical and biological sensors based on polythiophenes Hoang-Anh Ho and Mario Leclerc 22.1 Introduction 22.2 Different types of polythiophenes for chemical and biological sensors 22.3 Chemical sensors 22.4 Biological sensors 22.5 Conclusions References Index