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Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics, 2 Volume Set

ISBN: 978-0-470-74554-0
910 pages
July 2009
Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics, 2 Volume Set (0470745541) cover image
This essential resource consists of a series of critical reviews written by leading scientists, summarising the progress in the field of conjugated thiophene materials. It is an application-oriented book, giving a chemists’ point of view on the state-of-art and perspectives of the field. While presenting a comprehensive coverage of thiophene-based materials and related applications, the aim is to show how the rational molecular design of materials can bring a new breadth to known device applications or even aid the development of novel application concepts. The main topics covered include synthetic methodologies to thiophene-based materials (including the chemistry of thiophene, preparation of oligomers and polymerisation approaches) and the structure and physical properties of oligo- and polythiophenes (discussion of structural effects on electronic and optical properties). Part of the book is devoted to the optical and semiconducting properties of conjugated thiophene materials for electronics and photonics, and the role of thiophene-based materials in nanotechnology.
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Foreword by Professor Fred Wudl


List of Contributors

Volume One: Synthesis and Theory

1 Functional oligothiophene-based materials: nanoarchitectures and applications

Amaresh Mishra, Chang-Qi Ma, José L. Segura and Peter Bäuerle

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



2 Synthesis, characterization and properties of regioregular polythiophene-based materials

Paul C. Ewbank, Mihaela C. Stefan, Geneviève Sauvé 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


3 Fused oligothiophenes

Peter J. Skabara

3.1 Introduction

3.2 Synthesis and molecular properties of fused oligothiophenes

3.3 Conclusion


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



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


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


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



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



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


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



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



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



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


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



15 Polythiophenes as active electrode materials for electrochemical capacitors Daniel Bélanger

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



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


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


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



19 Thiophene-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



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


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


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



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"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)
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