Comparison of thiophene-pyrrole oligomers with oligothiophenes: A joint experimental and theoretical investigation of their structural and spectroscopic properties

María Moreno Oliva, Ted M. Pappenfus, Jacob H. Melby, Kathryn M. Schwaderer, Jared C. Johnson, Kari A. McGee, Demetrio A. Da Silva Filho, Jean-Luc Bredas, Juan Casado, Juan T. López Navarrete

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

We have prepared a new series of mixed thiophene-pyrrole oligomers to investigate the electronic benefits arising from the combination of these two heterocycles. The oligomers are functionalized with several hexyl and aryl groups to improve both processability and chemical robustness. An analysis of their spectroscopic (absorption and emission), photophysical, electrochemical, solid state, and vibrational properties is performed in combination with quantum-chemical calculations. This analysis provides relevant information regarding the use of these materials as organic semiconductors. The balance between the high aromatic character of pyrrole and the moderate aromaticity of thiophene allows us to address the impact of the coupling of these heterocycles in conjugated systems. The data are interpreted on the basis of the aromaticity, molecular conformations, ground and excited electronic state structures, frontier orbital topologies and energies, oxidative states, and quinoidal versus aromatic competition.

Original languageEnglish (US)
Pages (from-to)6866-6876
Number of pages11
JournalChemistry - A European Journal
Volume16
Issue number23
DOIs
StatePublished - Jun 18 2010

Keywords

  • Heterocycles
  • Oligomers
  • Oligothiophenes
  • Quantum chemistry
  • Semiconductors

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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