2013 Fiscal Year Final Research Report
Synthesis of novel redox systems having thiophenes highly integrated with quinone methides structure
| Project/Area Number |
23550053
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Fukui University of Technology (2013)
Osaka University (2011-2012) |
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Principal Investigator |
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| Project Period (FY) |
2011 – 2013
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| Keywords | キノメチド / チオフェン / フェノール / キノン / 酸化還元 / 立体障害 |
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| Research Abstract |
We have been interested in conjugated thiophene systems whose all hydrogen atoms are substituted by 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dienone (quinone-methide) structure. We have prepared thiophene and bithiophene derivatives (we named them "tetraquinothiophene"(1) and "hexaquinobithiohene"(2), respectively). These attract attention in term of dynamic multi-stage redox system as well as cross conjugated system adopting sulfur atom. Compounds 1 and 2 were synthesized from bromothiophene derivatives via Suzuki-Miyaura coupling. The structure of 1 was determined by X-ray analysis. There were little torsion of pinch-bonds and central five membered ring formed twist boat like conformation. The electrochemical properties of 1 and 2 were examined by cyclic voltammetry and the first reduction waves of them were observed irreversibly. It indicates conformational changes occur with one-electron reduction about both 1 and 2.
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[Journal Article] 3, 14-Bis(p-nitro phenyl)-17, 17-dipentyltetrabenzo[a, c, g, i]-fluo rene : A New Fluorophore Displaying Both Remarkable Solvatochromism and Crystalline-Induced Emission2013
Author(s)
Yoshiaki Ueda, Yusuke Tanigawa, Chitoshi Kitamura, Hiroshi Ikeda, Yuichi Yoshimoto, Mirai Tanaka, Kazuhiko Mizuno, Hiroyuki Kurata, Takeshi Kawase
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Journal Title
Chemistry- An Asian Journal
Volume: 8(2)
Pages: 392-399
DOI
Peer Reviewed
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