title: Pinpoint-fluorinated phenacenes: new synthesis and solubility enhancement strategies.
abstract: The Pd(II)-catalyzed cyclizations of 2,2-difluorovinylated biaryls, following a Friedel-Crafts-type mechanism, provide a new route to pinpoint-fluorinated phenacenes. The single fluorine substituent stabilized the synthesized fluoropicenes (fluoro[5]phenacenes) toward aerial oxidation and contributed to their solubility in organic solvents. For example, 6- and 13-fluoropicenes were 25- and 15-fold more soluble in THF than nonfluorinated picene. X-ray crystal structure analysis revealed that the fluorine substituent did not alter molecular planarity.
authors: Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba , Tsukuba, Ibaraki 305-8571, Japan.
authors: Kohei
authors: K
authors: Fuchibe
authors: Toshiyuki
authors: T
authors: Morikawa
authors: Kento
authors: K
authors: Shigeno
authors: Takeshi
authors: T
authors: Fujita
authors: Junji
authors: J
authors: Ichikawa