Structural and electronic effects of 1,3,4-thiadiazole units incorporated into polythiophene chains

Hao Pang, Peter J. Skabara, David J. Crouch, Warren Duffy, Martin Heeney, Iain McCulloch, Simon J. Coles, Peter N. Horton, Michael B. Hursthouse

Research output: Contribution to journalArticlepeer-review

50 Scopus citations

Abstract

A series of conjugated triaryl compounds have been synthesized, consisting of thiophene or selenophene peripheral units and a central 1,3,4-thiadiazole (TDA) heterocycle. X-ray crystallographic studies on four of the materials reveal that the molecules are planar in the solid state and feature an array of intramolecular (heteroatomic) and intermolecular (heteroatomic and π-π) noncovalent close contacts. Electrochemical oxidative polymerization affords insoluble polymers for EDOT-TDA-EDOT and EDTT-TDA-EDTT. The band gaps of the polymers have been deduced by cyclic voltammetry and electronic absorption spectroscopy and were found to be 1.8-1.9 eV. Both polymers show good stability toward n-doping and the EDTT analogue is more readily reduced than the EDOT-containing system. The enhanced stability toward n-doping, compared with the homopolymers PEDTT and PEDOT, is attributed to the presence of the electron deficient thiadiazole unit. The LUMO of poly(EDTT-TDA-EDTT) is 0.3 eV lower than that of poly(EDOT-TDA-EDOT), demonstrating that the substituent effect of the chalcogen atom is an important contributor to the electronic properties of the polymers. © 2007 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)6585-6593
Number of pages9
JournalMacromolecules
Volume40
Issue number18
DOIs
StatePublished - Sep 4 2007
Externally publishedYes

Bibliographical note

Generated from Scopus record by KAUST IRTS on 2023-02-14

ASJC Scopus subject areas

  • Materials Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

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