Synthesis and properties of thiophene-fused benzocarborane |
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| Authors: | Yasuhiro Morisaki Masato Tominaga Yoshiki Chujo |
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| Institution: | Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510 (Japan), Fax: (+81)?75-383-2607. ymo@chujo.synchem.kyoto-u.ac.jp. |
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| Abstract: | The o-carborane-based π-conjugated compound, benzocarborano- 2,1-b:3,4-b']dithiophene was synthesized. Its crystal structure revealed high coplanarity for the two thiophene rings of the 2,2'-bithiophene skeleton, which is fixed in the cisoid structure by the o-carborane unit. Theoretical calculations indicated non-aromaticity for its center C(6) ring moiety as well as decreased HOMO and LUMO levels. The o-carborane moiety provides an electron-withdrawing character to the 2,2'-bithiophene unit through an inductive effect. |
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