1085512-86-2Relevant academic research and scientific papers
Synthesis and crystal structure of 5,12-diphenyl-6,11-bis(thien-2-yl)tetracene
Hou, Yanhui,Chi, Xiaoliu,Wan, Xiangjian,Chen, Yongsheng
experimental part, p. 265 - 270 (2009/02/06)
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 NaBH3CN in the presence of weak Lewis acid ZnI2. A rearranged byproduct, 6,11-dihydro-5,12-diphenyl-6,6′-bis(thien-2-yl)-11,11′-dihyd rotetracene (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′-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 π-π overlap among the tetracene rings or among the pendant phenyl rings and thienyl rings.
