TY - JOUR
T1 - Synthesis of Tetra(3-thienyl)biphenoquinone and its Charge Transfer Complex with Perylene
AU - Fujii, Ryotaro
AU - Hossain, Md Awlad
AU - Akimoto, Hisato
AU - Hirabayashi, Kazunori
AU - Shimizu, Toshio
AU - Akiyama, Kazuhiko
AU - Goto, Kenta
AU - Nishikawa, Hiroyuki
AU - Yamashita, Ken Ichi
AU - Sugiura, Ken Ichi
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI Grant Number JP17H05379 (Coordination Asymmetry), the Cooperative Research Program of “Network Joint Research Center for Materials and Devices: Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” Grant Number 20173070, and the Priority Research Program sponsored by the Asian Human Resources Fund of Tokyo Metropolitan Government (TMG). Md. Awlad Hossain is grateful to Tokyo Metropolitan University (TMU) for a pre-doctoral fellowship. We thank Professor Shiro Kubuki for allowing us to use the instruments for DSC. We appreciate the technical assistance provided by Mr. Taisuke Matsumoto (Institute for Materials Chemistry and Engineering, Kyushu University), for diffraction studies, and the Service Centre of the Elementary Analysis of Organic Compounds at Kyushu University.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/1
Y1 - 2018/1
N2 - Tetra(thienyl)biphenoquinones were designed and synthesized. An oxidative coupling of 2,6-bis(3-thienyl)phenol with PbO2 in acetic acid afforded the corresponding biphenoquinone along with 2,6-bis(3-thienyl)-p-benzoquinone. This biphenoquinone showed properties characteristic of a π-expanded quinone, that is, positively shifted reduction potential and light absorption in the visible region. In contrast to kinetically protected biphenoquinones with bulky substituents at the ortho-positions of carbonyls, the title compounds take a planar structure because of the small steric repulsion of the five-membered thiophene rings. Its charge transfer complex with perylene is characterized by a well-overlapped mixed stack.
AB - Tetra(thienyl)biphenoquinones were designed and synthesized. An oxidative coupling of 2,6-bis(3-thienyl)phenol with PbO2 in acetic acid afforded the corresponding biphenoquinone along with 2,6-bis(3-thienyl)-p-benzoquinone. This biphenoquinone showed properties characteristic of a π-expanded quinone, that is, positively shifted reduction potential and light absorption in the visible region. In contrast to kinetically protected biphenoquinones with bulky substituents at the ortho-positions of carbonyls, the title compounds take a planar structure because of the small steric repulsion of the five-membered thiophene rings. Its charge transfer complex with perylene is characterized by a well-overlapped mixed stack.
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U2 - 10.1002/ajoc.201700560
DO - 10.1002/ajoc.201700560
M3 - Article
AN - SCOPUS:85034048811
SN - 2193-5807
VL - 7
SP - 171
EP - 178
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 1
ER -