Synthesis and electrochemical properties of a chiral silyl-substituted tetrathiafulvalene derivative

A new chiral tetrathiafulvalene (TTF) derivative and related silyl-substituted 1,3-dithiole-2-(thi)one compounds were synthesized and characterized by 1H NMR, 13C NMR, MS and IR spectra. Single crystal structure of the silyl-substituted 1,3-dithiole-2-one revealed the high degree of conjugation of the five-membered ring moiety in the compound. The electrochemical properties of the new TTF derivative were studied by cyclic voltammetry and the results indicated that the electron-donating ability of the chiral TTF derivative was similar to that of BEDT-TTF. The ΔE value for the new TTF derivative was smaller than those for TTF and BEDT-TTF, indicative of decreased Coulombic repulsion in the dicationic redox state. Formation of charge-transfer (CT) complex between the new donor and electron acceptor 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was demonstrated.

Graphical abstractElectrochemical properties of a new chiral tetrathiafulvalene (TTF) derivative were studied by cyclic voltammetry. Formation of CT complex between the new donor and acceptor DDQ was demonstrated.Figure optionsDownload full-size imageDownload as PowerPoint slide