An Efficient Method for Synthesizing Substituted Naphtho-1,3-dithiole-2-thiones from Tetrachlorotetrathionaphthalene and Sodium Trithiocarbonate

摘要

Two types of naphtho-fused 1,3-dithiole-2-thiones (2a-f and 4a-d) were obtained by the reaction of 3,4,7,8-tetrachloronaphtho[1,8-cd:5,6-c'd']bis (1,2-dithiole) (1) and sodium trithiocarbonate. The dechalcogenization of the thiones, using mercury acetate, leads to the corresponding naphtho-1,3-dithiol-2-ones (3a-d and 5a-d). The structures of 3a and 4a were confirmed by X-ray investigation. The tetrathiafulvalenes (TTFs) 6 and 7 were synthesized from 2d and 3c by coupling of the starting compounds with the help of triethyl phosphite. Using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) the TTFs were converted into semiconducting charge-transfer complexes.