Facile synthesis of picene from 1,2-Di(1-naphthyl)ethane by 9-fluorenone-sensitized photolysis

Hideki Okamoto; Minoru Yamaji; Shin Gohda; Yoshihiro Kubozono; Noriko Komura; Kaori Sato; Hisako Sugino; Kyosuke Satake

doi:10.1021/ol200874q

Facile synthesis of picene from 1,2-Di(1-naphthyl)ethane by 9-fluorenone-sensitized photolysis

Hideki Okamoto, Minoru Yamaji, Shin Gohda, Yoshihiro Kubozono, Noriko Komura, Kaori Sato, Hisako Sugino, Kyosuke Satake

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

35 Citations (Scopus)

Abstract

A facile formation of picene was achieved by photosensitization of 1,2-di(1-naphthyl)ethane using 9-fluorenone as a sensitizer. This sensitized photoreaction is the first photochemical cyclization of ethylene-bridged naphthalene moieties to afford the picene skeleton. 5,8-Dibromopicene, prepared by this procedure using 1,2-di[1-(4-bromonaphthyl)]ethane as the substrate, was readily converted to novel functionalized picenes by conventional substitution and cross-coupling reactions.

Original language	English
Pages (from-to)	2758-2761
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	10
DOIs	https://doi.org/10.1021/ol200874q
Publication status	Published - May 20 2011

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Facile synthesis of picene from 1,2-Di(1-naphthyl)ethane by 9-fluorenone-sensitized photolysis",

abstract = "A facile formation of picene was achieved by photosensitization of 1,2-di(1-naphthyl)ethane using 9-fluorenone as a sensitizer. This sensitized photoreaction is the first photochemical cyclization of ethylene-bridged naphthalene moieties to afford the picene skeleton. 5,8-Dibromopicene, prepared by this procedure using 1,2-di[1-(4-bromonaphthyl)]ethane as the substrate, was readily converted to novel functionalized picenes by conventional substitution and cross-coupling reactions.",

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T1 - Facile synthesis of picene from 1,2-Di(1-naphthyl)ethane by 9-fluorenone-sensitized photolysis

AU - Okamoto, Hideki

AU - Yamaji, Minoru

AU - Gohda, Shin

AU - Kubozono, Yoshihiro

AU - Komura, Noriko

AU - Sato, Kaori

AU - Sugino, Hisako

AU - Satake, Kyosuke

PY - 2011/5/20

Y1 - 2011/5/20

N2 - A facile formation of picene was achieved by photosensitization of 1,2-di(1-naphthyl)ethane using 9-fluorenone as a sensitizer. This sensitized photoreaction is the first photochemical cyclization of ethylene-bridged naphthalene moieties to afford the picene skeleton. 5,8-Dibromopicene, prepared by this procedure using 1,2-di[1-(4-bromonaphthyl)]ethane as the substrate, was readily converted to novel functionalized picenes by conventional substitution and cross-coupling reactions.

AB - A facile formation of picene was achieved by photosensitization of 1,2-di(1-naphthyl)ethane using 9-fluorenone as a sensitizer. This sensitized photoreaction is the first photochemical cyclization of ethylene-bridged naphthalene moieties to afford the picene skeleton. 5,8-Dibromopicene, prepared by this procedure using 1,2-di[1-(4-bromonaphthyl)]ethane as the substrate, was readily converted to novel functionalized picenes by conventional substitution and cross-coupling reactions.

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Facile synthesis of picene from 1,2-Di(1-naphthyl)ethane by 9-fluorenone-sensitized photolysis

Abstract

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