Bandgap engineering through controlled oxidation of polythiophenes

Sujun Wei, Jianlong Xia, Emma J. Dell, Yivan Jiang, Rui Song, Hyunbok Lee, Philip P. Rodenbough, Alejandro L. Briseno, Luis M. Campos

Research output: Contribution to journalArticle

Abstract

The use of Rozen's reagent (HOF×CH 3 CN) to convert polythiophenes to polymers containing thiophene-1,1-dioxide (TDO) is described. The oxidation of polythiophenes can be controlled with this potent, yet orthogonal reagent under mild conditions. The oxidation of poly(3- alkylthiophenes) proceeds at room temperature in a matter of minutes, introducing up to 60 % TDO moieties in the polymer backbone. The resulting polymers have a markedly low-lying lowest unoccupied molecular orbital (LUMO), consequently exhibiting a small bandgap. This approach demonstrates that modulating the backbone electronic structure of well-defined polymers, rather than varying the monomers, is an efficient means of tuning the electronic properties of conjugated polymers. Rusted root: Rozen's reagent (HOF×CH 3 CN) can convert polythiophenes to polythiophene-1,1- dioxides. The oxidation of thiophene-containing polymers, including telechelic polythiophenes, can be controlled with this potent, yet orthogonal reagent under mild conditions. By modulating the backbone of well-defined polymers, rather than varying the monomers, this approach provides an efficient means to tune their electronic properties.

Original languageEnglish (US)
Pages (from-to)1832-1836
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number7
DOIs
StatePublished - Feb 10 2014

Fingerprint

Polymers
Energy gap
Thiophenes
Oxidation
Electronic properties
Thiophene
Monomers
Conjugated polymers
Molecular orbitals
Electronic structure
polythiophene
Tuning
Temperature

Keywords

  • donor-acceptor systems
  • n-type materials
  • polythiophene
  • Rozen's reagent

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Wei, S., Xia, J., Dell, E. J., Jiang, Y., Song, R., Lee, H., ... Campos, L. M. (2014). Bandgap engineering through controlled oxidation of polythiophenes. Angewandte Chemie - International Edition, 53(7), 1832-1836. https://doi.org/10.1002/anie.201309398

Bandgap engineering through controlled oxidation of polythiophenes. / Wei, Sujun; Xia, Jianlong; Dell, Emma J.; Jiang, Yivan; Song, Rui; Lee, Hyunbok; Rodenbough, Philip P.; Briseno, Alejandro L.; Campos, Luis M.

In: Angewandte Chemie - International Edition, Vol. 53, No. 7, 10.02.2014, p. 1832-1836.

Research output: Contribution to journalArticle

Wei, S, Xia, J, Dell, EJ, Jiang, Y, Song, R, Lee, H, Rodenbough, PP, Briseno, AL & Campos, LM 2014, 'Bandgap engineering through controlled oxidation of polythiophenes', Angewandte Chemie - International Edition, vol. 53, no. 7, pp. 1832-1836. https://doi.org/10.1002/anie.201309398
Wei, Sujun ; Xia, Jianlong ; Dell, Emma J. ; Jiang, Yivan ; Song, Rui ; Lee, Hyunbok ; Rodenbough, Philip P. ; Briseno, Alejandro L. ; Campos, Luis M. / Bandgap engineering through controlled oxidation of polythiophenes. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 7. pp. 1832-1836.
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