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Author
Ji, Zhenfei Graduate School of Natural Science and Technology, Okayama University
Cheng, Zeliang Graduate School of Natural Science and Technology, Okayama University
Mori, Hiroki Research Institute for Interdisciplinary Science, Okayama University
Nishihara, Yasushi Research Institute for Interdisciplinary Science, Okayama University ORCID Kaken ID publons researchmap
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, C-8-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 pi-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.
Keywords
phenacene-type compounds
thiophene ring
cross-coupling
alkyl side chains
UV-vis absorption
p-type organic semiconductors
organic field-effect transistor (OFET)
Published Date
2020-08-24
Publication Title
Molecules
Volume
volume25
Issue
issue17
Publisher
MDPI
Start Page
3842
ISSN
1420-3049
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
Copyright Holders
© 2020 by the authors.
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DOI
Web of Science KeyUT
Related Url
isVersionOf https://doi.org/10.3390/molecules25173842
License
http://creativecommons.org/licenses/by/4.0/
Funder Name
Ministry of Education, Culture, Sports, Science and Technology
助成番号
15H00751