Synthesis of Tetrasilatetrathia[8]circulenes by a Fourfold Intramolecular Dehydrogenative Silylation of C−H Bonds

Yuma Serizawa; Shuhei Akahori; Shohei Kato; Hayato Sakai; Taku Hasobe; Yoshihiro Miyake; Hiroshi Shinokubo

doi:10.1002/chem.201700729

Synthesis of Tetrasilatetrathia[8]circulenes by a Fourfold Intramolecular Dehydrogenative Silylation of C−H Bonds

Yuma Serizawa, Shuhei Akahori, Shohei Kato, Hayato Sakai, Taku Hasobe, Yoshihiro Miyake, Hiroshi Shinokubo

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

The first two examples of a tetrasilatetrathia[8]circulene were synthesized in two steps from a tetraiodotetrathienylene by using a fourfold intramolecular dehydrogenative silylation of C−H bonds as the key step. A single-crystal X-ray diffraction analysis revealed that tetrasilatetrathia[8]circulene contains a perfectly planar [8]radialene skeleton. The excited-state dynamics of tetrasilatetrathia[8]circulene were evaluated by steady-state and time-resolved spectroscopic measurements, revealing an efficient intersystem crossing in the excited state.

Original language	English
Pages (from-to)	6948-6952
Number of pages	5
Journal	Chemistry - A European Journal
Volume	23
Issue number	29
DOIs	https://doi.org/10.1002/chem.201700729
Publication status	Published - 2017 May 23

Keywords

annulation
circulenes
silylation
thiophenes

ASJC Scopus subject areas

Chemistry(all)
Catalysis
Organic Chemistry

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10.1002/chem.201700729

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abstract = "The first two examples of a tetrasilatetrathia[8]circulene were synthesized in two steps from a tetraiodotetrathienylene by using a fourfold intramolecular dehydrogenative silylation of C−H bonds as the key step. A single-crystal X-ray diffraction analysis revealed that tetrasilatetrathia[8]circulene contains a perfectly planar [8]radialene skeleton. The excited-state dynamics of tetrasilatetrathia[8]circulene were evaluated by steady-state and time-resolved spectroscopic measurements, revealing an efficient intersystem crossing in the excited state.",

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AU - Serizawa, Yuma

AU - Akahori, Shuhei

AU - Kato, Shohei

AU - Sakai, Hayato

AU - Hasobe, Taku

AU - Miyake, Yoshihiro

AU - Shinokubo, Hiroshi

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AB - The first two examples of a tetrasilatetrathia[8]circulene were synthesized in two steps from a tetraiodotetrathienylene by using a fourfold intramolecular dehydrogenative silylation of C−H bonds as the key step. A single-crystal X-ray diffraction analysis revealed that tetrasilatetrathia[8]circulene contains a perfectly planar [8]radialene skeleton. The excited-state dynamics of tetrasilatetrathia[8]circulene were evaluated by steady-state and time-resolved spectroscopic measurements, revealing an efficient intersystem crossing in the excited state.

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KW - circulenes

KW - silylation

KW - thiophenes

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Synthesis of Tetrasilatetrathia[8]circulenes by a Fourfold Intramolecular Dehydrogenative Silylation of C−H Bonds

Abstract

Keywords

ASJC Scopus subject areas

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