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Synfacts 2007(1): 0034-0034  
DOI: 10.1055/s-2006-955679
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Tetrasulfonamide Macrocycles

Contributor(s): Timothy M. Swager, Yong Yang
L. He*, Y. An, L. Yuan, W. Feng, M. Li, D. Zhang, K. Yamato, C. Zheng, X. C. Zeng, B. Gong*
Beijing Normal University, P. r. of China; State University of New York at Buffalo, Northern Illinois University, DeKalb and University of Nebraska, Lincoln, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

A new family of shape-persistent macrocycles based on sulfonamides is synthesized from aromatic diamines and disulfonyl chlorides. The macrocyles resemble calix[4]arenes. The ether side chains help maintain the cone conformation and removal of them leads to the 1,3-alternate conformation. The size of the cavities is tuned by the aromatic residues forming the macrocycles. For example, replacing the naphthalene residue by benzene results in the shrinking of the cavity size from 8.47 x 8.89 Å to 6.98 x 7.97 Å. The macrocycles are capable of specifically binding small molecules with complementary sizes. The macrocycles also show a tubular assembly in the solid state.