Bandgap engineering through controlled oxidation of polythiophenes

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

Research output: Contribution to journalArticle

Abstract

The use of Rozen's reagent (HOF×CH3CN) 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×CH3CN) 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

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Bandgap engineering through controlled oxidation of polythiophenes'. Together they form a unique fingerprint.

  • Cite this

    Wei, S., Xia, J., Dell, E. J., Jiang, Y., Song, R., Lee, H., Rodenbough, P., Briseno, A. L., & 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