π-Conjugated oligothiophene-anthracene co-oligomers: Synthesis, physical properties, and self-assembly

Jing Luo, Hemi Qu, Jun Yin, Xiaojie Zhang, Kuo-Wei Huang, Chunyan Chi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

A new class of oligothiophene-anthracene co-oligomers, 9,10-bis(2- dodecyloligothienylvinyl)anthracene T n A (n = 1, 2 and 3), were synthesized and characterized. The photophysical and electrochemical properties of these oligomers demonstrated an increased conjugation length with increasing number of thiophene units. These oligomers also exhibited relatively larger ionization potential values compared with pentacene and sexithiophene and thus are expected to show improved stability. The strong aggregation tendency and excimer formation for T 1 A and obvious aggregation effect for T 2 A in solution were observed from the concentration and temperature-dependent fluorescence spectra. In contrast, no obvious aggregation behavior could be observed for T 3 A in solution. Thermal behavior and self-assembly of these co-oligomers in solid state were studied by a combination of TGA, DSC, powder X-ray diffraction and polarizing optical microscope. Liquid crystalline phases were observed in T 2 A and T 3 A at elevated temperature while only a crystalline phase was found for T 1 A. Single-crystal structures of T 1 A and T 2 A revealed a lamellar packing mode with ordered intermolecular anthracene-to-anthracene and oligothiophene-to-oligothiophene π-π stacking and these qualify them as potential semiconductors in electronic devices.

Original languageEnglish (US)
Pages (from-to)8202-8211
Number of pages10
JournalJournal of Materials Chemistry
Volume19
Issue number43
DOIs
StatePublished - Nov 10 2009

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

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