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Synthesis of bitetrathiafulvalenes with FeCl3-mediated homo-coupling of tetrathiafulvalenylmagnesium bromide and formation of nanostructures from bitetrathiafulvalenes having long alkylthio chains
Authors:Yohei Honna  Hideo Enozawa  Masayoshi Takase  Masahiko Iyoda
Institution:a Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan
b Department of Chemistry, School of Science, Kitasato University, Sagamihara, Kanagawa 228-8555, Japan
Abstract:The FeCl3-mediated homo-coupling of 4,5-bis(alkylthio)-4′-tetrathiafulvalenylmagnesium bromide 5 produced the corresponding bitetrathiafulvalene derivatives 2a-d in moderate yields (25-51%). Bitetrathiafulvalenes 2c and 2d having long alkylthio chains formed nanostructures and showed bulk electric conductivities (σrt = 2.6 − 8.0 × 10−5 S cm−1) in the neutral state owing to the fastener effect. Interestingly, the nanofiber of tetrakis(dodecylthio)bitetrathiafulvalene 2d exhibited a p-type semiconductivity as detected by AFM.
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