Synthesis of self-threading bithiophenes and their structure-property relationships regarding cyclic side-chains with atomic precision

Yuki Ouchi, Kazunori Sugiyasu, Soichiro Ogi, Akira Sato, Masayuki Takeuchi

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

We have recently reported a self-threading polythiophene as a new family of insulated molecular wires. Herein, we focused on the structure-property relationships of the unique three-dimensional architecture of the monomer. We have synthesized nine self-threading bithiophene monomers that have cyclic side-chains of different size and flexibility: i.e., 21-, 22-, 23-, 24-, 26-, and 30-membered rings composed of paraffinic, olefinic, or alkynic chains. To investigate their structure-property relationships, 1H NMR spectroscopy, UV absorption, and fluorescence spectroscopy measurements were conducted. We found that cyclic side-chains define the movable range of the dihedral angle of the bithiophene backbone, thereby affecting its photophysical properties. Therefore, the ability to design a structure with atomic precision as described herein would lead to the fine-tuning of the electronic properties of insulated molecular wires.

Original languageEnglish
Pages (from-to)75-84
Number of pages10
JournalChemistry - An Asian Journal
Volume7
Issue number1
DOIs
Publication statusPublished - 2012 Jan 2
Externally publishedYes

Keywords

  • molecular wires
  • oligomers
  • side-chains
  • structure-property relationships
  • thiophenes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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