Synthesis, electrochemistry and self-assembled monolayers of novel tetrathiafulvalene (TTF) and pi-extended TTF (exTTF) disulfides.
The synthesis of a new series of tetrathiafulvalene (TTF) and pi-extended TTF (exTTF) disulfides and the electrochemical properties of self-assembled monolayers derived from these compounds are described. When the intermediate bromides 3 and 7 were reacted with thiourea, followed by basic hydrolysis, the expected thiol formation was not observed and only disulfides were obtained. A mechanism is proposed to explain the self-oxidation process of these compounds. For the first time SAMs of exTTF derivatives were prepared. Electrochemical data for SAMs of 6 and 8 reveal a single two-electron chemically reversible oxidation process to form a dicationic state, typical of the exTTF system. The SAMs are stable over extended periods of time and show electrochemical stability upon repeated potential scans.
Department of Chemistry, Clemson University, Clemson, South Carolina 29634, USA.
M Angeles
MA
Herranz
Lei
L
Yu
Nazario
N
Martín
Luis
L
Echegoyen