pH-Controlled Molecular Switches and the Substrate-Directed Self-Assembly of Molecular Capsules with a Calix[4]pyrrole Derivative

被引:35
作者
Cafeo, Grazia [1 ]
Kohnke, Franz H. [1 ]
Valenti, Luca [1 ]
White, Andrew J. P. [2 ]
机构
[1] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy
[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem, Chem Crystallog Lab, London SW7 2AZ, England
关键词
anions; calixpyrroles; capsules; hydrogen bonding; molecular recognition; self-assembly;
D O I
10.1002/chem.200800819
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
10 alpha.20 alpha-Bis(4-nitrophenyl)-calix[4]pyrrole (1) forms 1:1 complexes with anions of selected aromatic hydroxy acids in which the host orientation within the guest is controlled by a change in the pH value. Some bis-anionic guests, including those obtained from 4-hydroxybenzoic acid. 1,4- and 1,3-benzenedicarboxylic acids, induce the self-assembly of molecular capsules involving two molecules of the receptor. H-1 NMR data and solid-state structures of the 1:1 complex of 1 with p-C6H4(COOH)(COO-)+NMe4 and the 2:1 capsule [(1)(2)m-C6H4(COO-)(2)-(+NMe4)(2)] provide structural details in solution and in the solid state.
引用
收藏
页码:11593 / 11600
页数:8
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