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Systematic structure-property investigations on a series of alternating carbazole-thiophene oligomers.

Authors
  • Kato, Shin-ichiro
  • Shimizu, Satoru
  • Kobayashi, Atsushi
  • Yoshihara, Toshitada
  • Tobita, Seiji
  • Nakamura, Yosuke
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Jan 17, 2014
Volume
79
Issue
2
Pages
618–629
Identifiers
DOI: 10.1021/jo402416f
PMID: 24364802
Source
Medline
License
Unknown

Abstract

A series of alternating carbazole-thiophene oligomers, namely 2,7-linked carbazole-thiophene oligomers 1, 3, 5, 7, and 9 and 3,6-linked ones 2, 4, 6, 8, and 10, in which the molecular length was systematically elongated, were synthesized by Suzuki-Miyaura coupling reactions. The effects of the conjugation connectivity between the carbazole and thiophene moieties and the molecular length on the electronic, photophysical, and electrochemical properties of 1-10 were comprehensively investigated. In the present oligomer architectures, the connection with thiophene at the 2,7-positions of carbazole ensures π-conjugation to a high extent and high fluorescence quantum yields, while that at the 3,6-positions enhances the donor ability. The increase in the molecular length of the 2,7-linked oligomers effectively extends π-conjugation. The relationship between structural variations and photophysical properties was examined by fluorescence lifetime measurements in detail. The X-ray crystal structure of 6 was also disclosed.

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