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Synthesis and crystal structure of 5,12-diphenyl-6,11-bis(thien-2-yl)tetracene

✍ Scribed by Yanhui Hou; Xiaoliu Chi; Xiangjian Wan; Yongsheng Chen

Publisher: Elsevier Science
Year: 2008
Tongue: English
Weight: 278 KB
Volume: 889
Category: Article
ISSN: 0022-2860
DOI: 10.1016/j.molstruc.2008.02.007

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✦ Synopsis

5,12-Diphenyl-6,11-bis(thien-2-yl)tetracene (1) was prepared by reduction of 5,12-diphenyl-6,11-bis(thien-2-yl)-6,11-tetracenediol (3) with NaBH 3 CN in the presence of weak Lewis acid ZnI 2 . A rearranged byproduct, 6,11-dihydro-5,12-diphenyl-6,6 0 -bis(thien-2-yl)-11, 11 0 -dihydrotetracene (5), was also obtained under this condition. Treatment of compound 3 with HI or other strong Lewis acid led to rearrangement and afforded 5,12-diphenyl-6,6 0 -bis(thien-2-yl)tetracene-11-one (4). The structures of compounds 1, 4 and 5 were confirmed by single crystal X-ray diffraction. The central tetracene rings of molecules 1 are twisted and assemble into arrays with slip parallel molecules in the crystal structure. There is no p-p overlap among the tetracene rings or among the pendant phenyl rings and thienyl rings.

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