Handbook of Thiophene-Based Materials

Dr. Igor F. Perepichka is a senior research associate in the chemistry department of Durham University (UK), working with Professor Martin Bryce on self-organised nanostructures as part of the European Science Foundation programme. He was educated at Donetstsk Polytechnic and completed his PhD in organic chemistry in the Institute of Physical Organic and Coal Chemistry of the National Academy of Sciences of the Ukraine, where he started his career as an engineer and was later promoted to senior research scientist in 1989. Dr. Perepichka has been a Humboldt Fellow at Wuerzburg University, a visiting scientist at CNRS in Angers and an invited professor at Angers University.Professor Dmitrii F. Perepichkais an assistant professor in the department of chemistry at McGill University in Montreal (Canada). He was educated at Donetsk State University (Ukraine) and completed his PhD in organic chemistry at the Ukraine National Academy of Science in the Ukraine in 1999. He spent two years as a postdoctoral researcher with Professor Martin Bryce and then from 2001 to 2003 he worked in the lab of Professor Fred Wudl at UCLA, working on a number of projects including the synthesis of conjugated polymers and the functionalisation of carbon nanotubes. His main research interests are materials chemistry, organic synthesis, molecular electronics, surface and nanoscience.

"A well-referenced introduction to the broad field of thiophene-based materials and their applications. ... A worthy addition to the collection of both those looking to enter the field and the seasoned researcher of conjugated polymers." (Angewandte Chemie International Edition, 2010)

• Foreword by Professor Fred Wudl PrefaceList of ContributorsVolume One: Synthesis and Theory1 Functional oligothiophene-based materials: nanoarchitectures and applicationsAmaresh Mishra, Chang-Qi Ma, José L. Segura and Peter Bäuerle1.1 Introduction1.2 Functionalized oligothiophenes1.3 Fused thiophenes1.4 Macrocyclic thiophenes1.5 Dendritic and hyperbranched oligothiophenes1.6 Conclusions and prospectsAcknowledgmentsReferences2 Synthesis, characterization and properties of regioregular polythiophene-based materialsPaul C. Ewbank, Mihaela C. Stefan, Geneviève Sauvé and Richard D. McCullough2.1 Introduction2.2 Consequences of regiochemistry2.3 Synthesis of regioregular polythiophenes2.4 Purification and fractionation2.5 Molecular characterization2.6 Solid-state studies2.7 Block copolymers containing regioregular polythiophenes2.8 ConclusionsReferences3 Fused oligothiophenesPeter J. Skabara3.1 Introduction3.2 Synthesis and molecular properties of fused oligothiophenes3.3 ConclusionReferences4 Thiophene-S,S-dioxides as a class of electron-deficient materials for electronics and photonicsGiovanna Barbarella and Manuela Melucci4.1 Introduction4.2 Electrochemical and photoluminescence properties4.3 Application in devices4.4 ConclusionAcknowledgmentsReferences5 Synthesis and properties of oligo- and polythiophenes containing transition metalsMichael O. Wolf5.1 Introduction5.2 Transition metal-containing oligothiophenes5.3 Electropolymerization and properties of polymers5.4 Conclusion and outlookReferences6 Selenophenes as hetero-analogues of thiophene-based materialsTetsuo Otsubo and Kazuo Takimiya6.1 Introduction6.2 Selenophene-based conducting materials6.3 Selenophene-based electroactive materials6.4 Selenophene-based OFET materials6.5 ConclusionReferences7 Energy gaps and their control in thiophene-based polymers and oligomersMiklos Kertesz, Shujiang Yang and Yonghui Tian7.1 Introduction7.2 Oligomer vs PBC calculations of the bandgap7.3 Gap and connectivity7.4 Bandgap affected by an aromatic vs quinonoid valence tautomerism7.5 Is a small bandgap thiophene polymer attainable?7.6 Gaps of ladder-like PThs7.7 Substitutions and other factors influencing the gap7.8 ConclusionAcknowledgmentReferences8 Theoretical studies on thiophene-containing compoundsSanjio S. Zade and Michael Bendikov8.1 Introduction8.2 HOMO–LUMO gap and bandgap calculations8.3 Nature of charge carriers8.4 Effect of substitutions on different properties8.5 Twisting (inter-ring deviation from planarity) in oligo- and polythiophene8.6 IR and Raman spectra8.7 UV–Vis spectra8.8 Quinoid oligothiophene8.9 Cyclic oligothiophene8.10 New compounds with tailor-made properties8.11 ConclusionAcknowledgmentsReferencesVolume Two: Properties and Applications9 Electrochemistry of oligothiophenes and polythiophenesPhilippe Blanchard, Antonio Cravino and Eric Levillain9.1 Introduction9.2 Electrochemistry9.3 Spectroelectrochemistry9.4 ConclusionReferences10 Novel photonic responses from low-dimensional crystals of thiophene/phenylene oligomersHisao Yanagi, Fumio Sasaki, Shunsuke Kobayashi and Shu Hotta10.1 Introduction10.2 Low-dimensional crystals of thiophene/phenylene co-oligomers10.3 Amplified spontaneous emission10.4 Stimulated resonance Raman scattering10.5 Pulse-shaped emission with time delay10.6 ConclusionAcknowledgmentsReferences11 Novel electronic and photonic properties of thiophene-based oligomersShu Hotta11.1 Introduction11.2 Materials and molecular alignments: thin films and crystals11.3 Charge transport: FET device applications11.4 Photonic features: laser oscillation11.5 Implications of the optoelectronic data of the crystals11.6 Conclusion and future prospectsAcknowledgmentsReferences12 Liquid crystalline and electroresponsive polythiophenesKazuo Akagi12.1 Introduction12.2 Synthesis and properties of LC polythiophene derivatives12.3 FLC Polythiophene derivativesAcknowledgmentsReferences13 Self-assembly of thiophene-based materials: a scanning tunneling microscopy perspectiveClara Santato, Fabio Cicoira and Federico Rosei13.1 Introduction13.2 STM studies of thiophene-based materials13.3 Conclusions and perspectivesReferences14 PEDOT – properties and technical relevanceKnud Reuter, Stephan Kirchmeyer and Andreas Elschner14.1 Introduction14.2 Synthesis14.3 Properties14.4 Processing14.5 Uses14.6 ConclusionAcknowledgmentsReferences15 Polythiophenes as active electrode materials for electrochemical capacitors Daniel Bélanger15.1 Introduction15.2 Electrochemical capacitors15.3 Polythiophene derivatives15.4 Types of electrochemical capacitors15.5 Performance and prototypes15.6 ConclusionAcknowledgmentsReferences16 Electroactive oligothiophenes and polythiophenes for organic field effect transistorsAntonio Facchetti16.1 Introduction16.2 Field effect transistors16.3 Thiophene-based oligomers for OFETs16.4 Thiophene-based polymers for OFETs16.5 Conclusions and outlookReferences17 Thienothiophene-containing polymers for field effect transistor applicationsIain McCulloch and Martin Heeney17.1 Introduction to organic electronics17.2 Organic field effect transistors17.3 Organic semiconductors17.4 Thienothiophene polymers17.5 ConclusionReferences18 Photovoltaics based on thiophene polymers: a short overviewSuren A. Gevorgyan and Frederik C. Krebs18.1 Introduction18.2 Processing at higher levels18.3 Thermal processing to alter morphology18.4 Solvent vapor treatment to alter morphology18.5 Thermocleavage18.6 Other methods to control morphology18.7 ConclusionAcknowledgmentsReferences19 Thiophene-based materials for electroluminescent applicationsIgor F. Perepichka, Dmitrii F. Perepichka and Hong Meng19.1 Introduction19.2 General synthetic routes to PTs19.3 Thiophene homopolymers19.4 Thiophene oligomers19.5 Copolymers of thiophenes with other conjugated moieties19.6 Oligomers and polymers with thiophene-S,S-dioxide moiety19.7 Thiophene materials for unconventional and advanced electroluminescent applications19.8 ConclusionsAbbreviationsReferences20 Thiophene-based electrochromic materialsMuge Acik, Michael A. Invernale and Gregory A. Sotzing20.1 Electrochromism and electrochromics20.2 Electrochromism in polythiophene derivatives20.3 Organic versus inorganic20.4 Electrochromics in applications20.5 ConclusionReferences21 Photoresponsive thiophene-based molecules and materialsLuc Ubaghs, David Sud and Neil R. Branda21.1 Introduction21.2 Photochromism in single crystals21.3 Photochromism in amorphous films21.4 Photochromism in polymers21.5 Photochromism on metal surfaces21.6 New architectures21.7 ConclusionReferences22 Chemical and biological sensors based on polythiophenesHoang-Anh Ho and Mario Leclerc22.1 Introduction22.2 Different types of polythiophenes for chemical and biological sensors22.3 Chemical sensors22.4 Biological sensors22.5 ConclusionsReferencesIndex