Synthesis 2019; 51(24): 4576-4581
DOI: 10.1055/s-0039-1690206
paper
© Georg Thieme Verlag Stuttgart · New York

Sumanene Hexaester: An Electron-Deficient Buckybowl

Hideaki Toda
a  Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   Email: hsakurai@chem.eng.osaka-u.ac.jp
,
Yuta Uetake
a  Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   Email: hsakurai@chem.eng.osaka-u.ac.jp
,
Yumi Yakiyama
a  Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   Email: hsakurai@chem.eng.osaka-u.ac.jp
,
Hironobu Nakazawa
a  Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   Email: hsakurai@chem.eng.osaka-u.ac.jp
,
Takashi Kajitani
b  Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
,
Takanori Fukushima
b  Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
,
Hidehiro Sakurai
a  Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   Email: hsakurai@chem.eng.osaka-u.ac.jp
› Author Affiliations
This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas ‘π-Figuration’ (no. 26102002 for H.S. and no. 26102008 for T.F.) and ‘Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials’ from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
Further Information

Publication History

Received: 19 August 2019

Accepted after revision: 12 September 2019

Publication Date:
30 September 2019 (online)

Abstract

2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexa­substituted sumanene with CO2Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation­ using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.

Supporting Information

 
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