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  • Title: Synthesis, electrochemistry and self-assembled monolayers of novel tetrathiafulvalene (TTF) and pi-extended TTF (exTTF) disulfides.
    Author: Herranz MA, Yu L, Martín N, Echegoyen L.
    Journal: J Org Chem; 2003 Oct 31; 68(22):8379-85. PubMed ID: 14575461.
    Abstract:
    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.
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