Shape-Persistent Macrocyclic Aromatic Tetrasulfonamides: Molecules with Nanosized Cavities and their Nanotubular Assemblies in Solid State

Authors

Lan He, Beijing Normal University
Yu An, Beijing Normal University
Lihua Yuan, State University of New York at Buffalo
Wen Feng, State University of New York at Buffalo
Minfeng Li, Colleges of Chemistry and Resources Science and Technology, Beijing Normal University, Beijing 100875, China
Dechun Zhang, Colleges of Chemistry and Resources Science and Technology, Beijing Normal University, Beijing 100875, China
Kazuhiro Yamato, State University of New York at Buffalo
Chong Zheng, Northern Illinois University
Xiao Cheng Zeng, University of Nebraska-LincolnFollow
Bing Gong, State University of New York at Buffalo

Date of this Version

7-18-2006

Comments

Published in Proceedings of the National Academy of Sciences of the United States of America 103:29 (July 18, 2006), pp. 10850-10855. doi: 10.1073/pnas.0602912103 Copyright © 2006 by The National Academy of Sciences of the USA. Used by permission.

Abstract

Alkoxy side-chain-flanked diarylsulfonamide serves as a reliable structural motif for constructing macrocyclic aromatic tetrasulfonamides. This 90° structural motif is persistent both in solution and in the solid state, which allows the one-step formation of tetrasulfonamide macrocycles. These macrocycles adopt a cone-shaped conformation in solution and in the solid state. For each molecule, an interior cavity surrounded by the aromatic residues is formed. The cavity sizes of the macrocycles can be tuned by incorporating aromatic residues of proper sizes. Guest (solvent) molecules are found in the cavities and bound by side chains. In solution, ¹H NMR shows that the cone conformations undergo rapid interconversion at room temperature. The alkoxy side chains are found to be indispensable for maintaining the cone conformation. In addition, these porous molecules self-assemble into hollow tubular structures in the solid state. A variety of host molecules and building blocks for constructing nanoporous solid-state structures can be expected from these molecules.