Synthesis and physicochemical properties of 2,7-disubstituted phenanthro[2,1-b:7,8-b']dithiophenes

Zhenfei Ji, Zeliang Cheng, Hiroki Mori, Yasushi Nishihara

Research output: Contribution to journalArticlepeer-review

Abstract

We report the design, synthesis, and physicochemical properties of an array of phenanthro[2,1-b:7,8-b']dithiophene (PDT-2) derivatives by introducing five types of alkyl (CnH2n+1; n = 8, 10, 12, 13, and 14) or two types of decylthienyl groups at 2,7-positions of the PDT-2 core. Systematic investigation revealed that the alkyl length and the type of side chains have a great effect on the physicochemical properties. For alkylated PDT-2, the solubility was gradually decreased as the chain length was increased. For instance, C8-PDT-2 exhibited the highest solubility (5.0 g/L) in chloroform. Additionally, substitution with 5-decylthienyl groups showed poor solubility in both chloroform and toluene, whereas PDT-2 with 4-decylthienyl groups resulted in higher solubility. Furthermore, UV-vis absorption of PDT-2 derivatives substituted by decylthienyl groups showed a redshift, indicating the extension of their π-conjugation length. This work reveals that modification of the conjugated core by alkyl or decylthienyl side chains may be an efficient strategy by which to change the physicochemical properties, which might lead to the development of high-performance organic semiconductors.

Original languageEnglish
Article number25173842
JournalMolecules
Volume25
Issue number17
DOIs
Publication statusPublished - Sep 2020

Keywords

  • Alkyl side chains
  • Cross-coupling
  • Organic field-effect transistor (OFET)
  • P-type organic semiconductors
  • Phenacene-type compounds
  • Thiophene ring
  • UV-vis absorption

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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