T. Nozdryn, J. Favard, J. Cousseau
Dec 5, 1997
Citations
0
Influential Citations
4
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Polyfluoroalkylsulfanyl-substituted tetrathiafulvalene derivatives have been synthesised via self- or cross-coupling of suitable 2-(thi)oxo-1, 3-dithioles. Key intermediates are 4,5-bis(polyfluoroalkyl-sulfanyl)-2-thioxo-1,3-dithioles, formed from reaction between 2-(F-alkyl)-1-iodoethanes C n F 2 n +1 −C 2 H 4 I ( n = 6,8) and bis(tetraethylammonium) bis(1,3-dithiole-2-thione-4,5-dithiolato)zincate, and 4-[2′-(F-hexyl-ethylsulfanyl]-5-methylsulfanyl-2-thioxo-1, 3-dithiole. Self- and cross-coupling products are formed in fair to very good yields by using tri-isopropylphosphite, instead of the more usual triethyl or trimethylphosphite. All of these new TTF-derivatives exhibit quasi reversible voltammograms. Cation radical salts have been obtained mainly from one of these derivatives, whose anodic oxidation, in the presence of tetrabutylammonium hexafluorophosphate or perchlorate, allows isolation of very thin ‘hair-like’ threads.