Pinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement Strategies

被引：52

作者：

Fuchibe, Kohei ^{[1
]}

Morikawa, Toshiyuki ^{[1
]}

Shigeno, Kento ^{[1
]}

Fujita, Takeshi ^{[1
]}

Ichikawa, Junji ^{[1
]}

机构：

[1] Univ Tsukuba, Fac Pure & Appl Sci, Div Chem, Tsukuba, Ibaraki 3058571, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 05期

关键词：

CRAFTS-TYPE CYCLIZATION; THIN-FILM TRANSISTORS; PENTACENE; 1,1-DIFLUORO-1-ALKENES; 1,1-DIFLUOROALLENES; DERIVATIVES; ACTIVATION; CHRYSENES; ALCOHOLS; PACKING;

D O I：

10.1021/ol503759d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1126 / 1129

页数：4

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