Synthesis and Crystal Structure of a [70]Fullerene–Pentacene Monoadduct

We succeeded in the first isolation of a single pure regioisomer of a C70–acene monoadduct. 1,9-Diels–Alder monoadducts of C70 with pentacene derivatives were obtained by not only the Diels–Alder reaction but also a one-pot reaction using stable dihydropentacene derivatives, 2,3-dichloro-5,6-dicyano...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2016-04, Vol.89 (4), p.437-443
Main Authors: Shirai, Hitoshi, Tajima, Tomoyuki, Kubo, Kentaro, Nishihama, Takuya, Miyake, Hideaki, Takaguchi, Yutaka
Format: Article
Language:English
Subjects:
Crystal structure
Derivatives
Diels-Alder reactions
Linkages
Pentacene
Stacks
Synthesis
X-rays
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Summary:We succeeded in the first isolation of a single pure regioisomer of a C70–acene monoadduct. 1,9-Diels–Alder monoadducts of C70 with pentacene derivatives were obtained by not only the Diels–Alder reaction but also a one-pot reaction using stable dihydropentacene derivatives, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), and C70. The X-ray crystallographic study of a single pure regioisomer 2b confirmed positions of the linkage between C70 and acenes for the first time, and revealed unique columnar stacks.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20150378