One- or two-dimensional fluorine segregation in amphiphilic perfluorinated tetrathiafulvalenes

Olivier Jeannin (1) , Marc Fourmigué (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

A perfluorinated tetrathiafulvalene (TTF) derivative 1, that is a bis(vinylenedithio)TTF substituted with -(CF2)3− chains on both ends, is prepared from the reaction of Na2dmit (dmit: 1,3-dithiole-2-thione-4,5-dithiolate) with 1,2-dichlorohexafluorocyclopentene, oxymercuration of the obtained dithiolethione to the corresponding dithiolone and phosphite coupling. An unsymmetrical TTF 2 fused with only one hexafluorocyclopenta[1,2-b]1,4-dithiine moiety is also described together with the X-ray crystal structures and electrochemical properties of 1 and 2. The amphiphilic character provided by the rigid −(CF2)3− moieties in 1 and 2 leads to a strong segregation of the aliphatic fluorinated moieties in the solid state, affording fluorinated columns or bilayer structural motifs. To cite this article: O. Jeannin, M. Fourmigué, C. R. Chimie 9 (2006).

Mots clés: Crystal engineering; Fluorine; Layered compounds; Tetrathiafulvalene

Domaines: Chimie-Physique [physics.chem-ph]; Chimie organique

Olivier Jeannin, Marc Fourmigué. One- or two-dimensional fluorine segregation in amphiphilic perfluorinated tetrathiafulvalenes. Comptes Rendus. Chimie, 2006, 9 (10), pp.1287-1294. ⟨10.1016/j.crci.2006.04.002⟩. ⟨hal-00189939⟩