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Synfacts 2007(8): 0821-0821  
DOI: 10.1055/s-2007-968784
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Low-Band-Gap Bowls

Contributor(s): Timothy M. Swager, Trisha L. Andrew
T. Amaya, K. Mori, H.-L. Wu, S. Ishida, J.-i. Nakamura, K. Murata, T. Hirao*
Osaka University and Nippon Shokubai Co., Ltd., Osaka, Japan
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

A facile synthetic method for functionalizing the three benzylic positions of suma­nene (1) is reported. Excellent (70% to quantitative) isolated yields are reported for a variety of aryl functionalizations, although lower yields are obtained when thiophene carboxaldehydes are employed. Compound 2 is notable for a low band gap (1.99 eV) that arises due to a lack of steric repulsion between the sumanene core and the thiophene arms.