Synthesis of bitetrathiafulvalenes with FeCl3-mediated homo-coupling of tetrathiafulvalenylmagnesium bromide and formation of nanostructures from bitetrathiafulvalenes having long alkylthio chains |
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Authors: | Yohei Honna Hideo Enozawa Masayoshi Takase Masahiko Iyoda |
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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 |
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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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