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

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, 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

Acknowledgments

References

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

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 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

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 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

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