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Paper | Special issue | Vol 54, No. 2, 2001, pp. 833 - 848
Published online:
DOI: 10.3987/COM-00-S(I)79
Syntheses, Structure and Conducting Properties of Halogenated Ethylene- dioxytetrathiafulvalenes

Masahiko Iyoda,* Yoshiyuki Kuwatani, Eiji Ogura, Kenji Hara, Hironori Suzuki, Takahiro Takano, Koji Takeda, Jun-ichi Takano, Kohei Ugawa, Masato Yoshida, Haruo Matsuyama, Hiroyuki Nishikawa, Isao Ikemoto, Takehiro Kato, Naoki Yoneyama, Jun-ichi Nishijo, Akira Miyazaki, and Toshiaki Enoki

*Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan

Abstract

4,5-Diiodo-, 4,5-dibromo-, and 4,5-dichloro-4',5'-ethylenedioxytetra-thiafulvalenes (EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2) were synthesized in moderate to good yields by the two routes. The first route contains the reaction of EDO-TTF with LDA, followed by quenching with halogenated reagents, and the second route consists of the P(OR)3-mediated cross-coupling of 4,5-dihalogenated 1,3-dithiole-2-ones with 4,5-ethylenedioxy-1,3-dithiole-2-thione. The structures of EDO-TTFI2 and EDO-TTFCl2 were determined by X-Ray analysis. The radical-cation salts derived from EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2 show high conductivities, although these compounds contain electron-withdrawing halogens as the substituent.

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