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 journalArticle

29 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 languageEnglish
Pages (from-to)2758-2761
Number of pages4
JournalOrganic Letters
Volume13
Issue number10
DOIs
Publication statusPublished - May 20 2011

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Ethane
Photolysis
ethane
photolysis
Photosensitivity Disorders
Cyclization
cross coupling
Cross Reactions
synthesis
musculoskeletal system
naphthalene
Skeleton
ethylene
Substitution reactions
substitutes
Substrates
9-fluorenone
picene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Facile synthesis of picene from 1,2-Di(1-naphthyl)ethane by 9-fluorenone-sensitized photolysis. / Okamoto, Hideki; Yamaji, Minoru; Gohda, Shin; Kubozono, Yoshihiro; Komura, Noriko; Sato, Kaori; Sugino, Hisako; Satake, Kyosuke.

In: Organic Letters, Vol. 13, No. 10, 20.05.2011, p. 2758-2761.

Research output: Contribution to journalArticle

Okamoto, Hideki ; Yamaji, Minoru ; Gohda, Shin ; Kubozono, Yoshihiro ; Komura, Noriko ; Sato, Kaori ; Sugino, Hisako ; Satake, Kyosuke. / Facile synthesis of picene from 1,2-Di(1-naphthyl)ethane by 9-fluorenone-sensitized photolysis. In: Organic Letters. 2011 ; Vol. 13, No. 10. pp. 2758-2761.
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