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Synfacts 2007(6): 0595-0595  
DOI: 10.1055/s-2007-968588
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Intermolecular Charge Transport in Self-Assembled Discs

Contributor(s): Timothy M. Swager, Anne J. McNeil
M. Hasegawa, H. Enozawa, Y. Kawabata, M. Iyoda*
Tokyo Metropolitan University, Japan
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

Iyoda and co-workers report the synthesis of a disk-like molecule containing six electroactive tetrathiafulvalenes and demonstrate that they form self-assembled nanowires. In situ deprotection of the TMS groups followed by six Sonogashira reactions provides the desired compound in 52% overall yield (˜90% yield per coupling). Hexakis(trimethylsilylethynyl)benzene was previously synthesized by Tobe and co-workers in one step from hexabromobenzene (Org. Lett. 2001, 3, 2419-2421). One-electron chemical oxidation by Fe(ClO4)3 and self-assembly provided fibers with hexagonal columnar packing and a conductivity of 1.1 x 10-3 S/cm.