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Synfacts 2010(4): 0418-0418  
DOI: 10.1055/s-0029-1219606
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Planarized Cyclooctatetraenes

Contributor(s): Timothy M. Swager, Birgit Esser
T. Ohmae, T. Nishinaga*, M. Wu, M. Iyoda*
Tokyo Metropolitan University, Japan
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

Planar cyclooctatetraene derivatives 1, 2, and 3 were synthesized that are embedded in cyclic tetrathiophene structures. The choice of the bridging atoms allows fine-tuning of the planarity of the central COT core. High ­degrees of antiaromaticity and narrow HOMO-LUMO gaps were calculated theoretically, and amphoteric redox properties were observed.