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Poly(thiophene)s

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Encyclopedia of Polymeric Nanomaterials

Synonyms

P3AT; P3HT; PT

Definition

Poly(thiophene)s are a class of conjugated polymer that are comprised of repeating units of thiophene or fused aromatic thiophene along the backbone. Often the thiophene rings contain alkyl side chains as solubilizing units to enable good processability of the polymer. They have promising performance in a range of applications.

Introduction

Within the realms of conjugated polymer research, thiophene-containing materials have been one of the most widely investigated materials. Thiophene-containing polymers have been investigated in almost every reported application of conjugated polymers, ranging from organic solar cells and organic field effects transistors to sensors, electrochromics, thermoelectric devices, and more [1]. The prevalence of thiophene as a comonomer in conjugated polymers is likely due to a combination of factors. It is readily available, and the chemistry of thiophene is well developed and understood, enabling the functionalization...

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References

  1. Guo X, Baumgarten M, Müllen K (2013) Designing π-conjugated polymers for organic electronics. Prog Poly Sci 38:1832–1908

    Article  CAS  Google Scholar 

  2. Krebs FC, Nyberg RB, Jorgensen M (2004) Influence of residual catalyst on the properties of conjugated polyphenylenevinylene materials: palladium nonaparticles and poor electrical performance. Chem Mater 16:1313–1318

    Article  CAS  Google Scholar 

  3. McCullough R (1998) The chemistry of conducting polythiophenes. Adv Mater 10:93–116

    Article  CAS  Google Scholar 

  4. Liu J, Kadnikova EN, Liu Y, McGehee MD, Fréchet JMJ (2004) Polythiophene containing thermally removable solubilizing groups enhances the interface and the performance of polymer−titania hybrid solar cells. J Am Chem Soc 126:9486–9487

    Article  CAS  Google Scholar 

  5. Bundgaard E et al (2012) Removal of solubilizing side chains at low temperature: a new route to native poly(thiophene). Macromolecules 45:3644–3646

    Article  CAS  Google Scholar 

  6. Brabec CJ, Heeney M, McCulloch I, Nelson J (2011) Influence of blend microstructure on bulk heterojunction organic photovoltaic performance. Chem Soc Rev 40:1185–1199

    Article  CAS  Google Scholar 

  7. Osaka I, McCullough RD (2008) Advances in molecular design and synthesis of regioregular polythiophenes. Acc Chem Res 41:1202–1214

    Article  CAS  Google Scholar 

  8. Sirringhaus H et al (1999) Two-dimensional charge transport in self-organized, high-mobility conjugated polymers. Nature 401:685–688

    Article  CAS  Google Scholar 

  9. Rivnay J, Mannsfeld SCB, Miller CE, Salleo A, Toney MF (2012) Quantitative determination of organic semiconductor microstructure from the molecular to device scale. Chem Rev 112:5488–5519

    Article  CAS  Google Scholar 

  10. Guo XG, Watson MD (2008) Conjugated polymers from naphthalene bisimide. Org Lett 10:5333–5336

    Article  CAS  Google Scholar 

  11. Ong BS, Wu Y, Li Y, Liu P, Pan H (2008) Thiophene polymer semiconductors for organic thin-film transistors. Chem Eur J 14:4766–4778

    Article  CAS  Google Scholar 

  12. McCulloch I et al (2009) Semiconducting thienothiophene copolymers: design, synthesis, morphology, and performance in thin-film organic transistors. Adv Mater 21:1091–1109

    Article  CAS  Google Scholar 

  13. Noriega R et al (2013) A general relationship between disorder, aggregation and charge transport in conjugated polymers. Nat Mater 12:1038–1044

    Article  CAS  Google Scholar 

  14. He M et al (2010) Importance of C2 symmetry for the device performance of a newly synthesized family of fused-ring thiophenes. Chem Mater 22:2770–2779

    Article  CAS  Google Scholar 

  15. Chochos CL, Choulis SA (2011) How the structural deviations on the backbone of conjugated polymers influence their optoelectronic properties and photovoltaic performance. Prog Polym Sci 36:1326–1414

    Article  CAS  Google Scholar 

  16. Rieger R, Beckmann D, Mavrinskiy A, Kastler M, Müllen K (2010) Backbone curvature in polythiophenes. Chem Mater 22:5314–5318

    Article  CAS  Google Scholar 

  17. Wang C, Dong H, Hu W, Liu Y, Zhu D (2011) Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics. Chem Rev 112:2208–2267

    Article  Google Scholar 

  18. Marrocchi A, Lanari D, Facchetti A, Vaccaro L (2012) Poly(3-hexylthiophene): synthetic methodologies and properties in bulk heterojunction solar cells. Energy Environ Sci 5:8457–8474

    Article  CAS  Google Scholar 

  19. Yokozawa T, Yokoyama A (2009) Chain-growth condensation polymerization for the synthesis of well-defined condensation polymers and pi-conjugated polymers. Chem Rev 109:5595–5619

    Article  CAS  Google Scholar 

  20. Bryan ZJ, McNeil AJ (2013) Conjugated polymer synthesis via catalyst-transfer polycondensation (CTP): mechanism, scope, and applications. Macromolecules 46:8395–8405

    Article  CAS  Google Scholar 

  21. Okamoto K, Luscombe CK (2011) Controlled polymerizations for the synthesis of semiconducting conjugated polymers. Polym Chem 2:2424–2434

    Article  CAS  Google Scholar 

  22. Marshall N, Sontag SK, Locklin J (2011) Surface-initiated polymerization of conjugated polymers. Chem Comm 47:5681–5689

    Article  CAS  Google Scholar 

  23. Scherf U, Gutacker A, Koenen N (2008) All-conjugated block copolymers. Acc Chem Res 41:1086–1097

    Article  CAS  Google Scholar 

  24. Sakamoto J, Rehahn M, Wegner G, Schluter AD (2009) Suzuki polycondensation: polyarylenes à la carte. Macromol Rapid Commun 30:653–687

    Article  CAS  Google Scholar 

  25. Liu M et al (2013) Synthesis of thiophene-containing conjugated polymers from 2,5-thiophenebis(boronic ester)s by Suzuki polycondensation. Polym Chem 4:895–899

    Article  CAS  Google Scholar 

  26. Carsten B, He F, Son HJ, Xu T, Yu L (2011) Stille polycondensation for synthesis of functional materials. Chem Rev 111:1493–1528

    Article  CAS  Google Scholar 

  27. Okamoto K, Zhang J, Housekeeper JB, Marder SR, Luscombe CK (2013) C–H arylation reaction: atom efficient and greener syntheses of π-conjugated small molecules and macromolecules for organic electronic materials. Macromolecules 46:8059–8078

    Article  CAS  Google Scholar 

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Barnes, G., Yau, C.P. (2014). Poly(thiophene)s. In: Kobayashi, S., Müllen, K. (eds) Encyclopedia of Polymeric Nanomaterials. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-36199-9_120-1

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  • DOI: https://doi.org/10.1007/978-3-642-36199-9_120-1

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