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.

• Authors: Hideki Okamoto, Minoru Yamaji, Shin Gohda, Yoshihiro Kubozono, Noriko Komura, Kaori Sato, Hisako Sugino, Kyosuke Satake
• Journal: Organic letters (Org Lett) Vol. 13 Issue 10 Pg. 2758-61 (May 20 2011) ISSN: 1523-7052 [Electronic] United States
• PMID: 21513300 (Publication Type: Journal Article)