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
相关论文
共 59 条
[1]  
AJAMI D, 2007, ANGEW CHEM, V119, P246
[2]   Assembly of hybrid synthetic capsules [J].
Ajami, Dariush ;
Schramm, Michael P. ;
Volonterio, Alessandro ;
Rebek, Julius, Jr. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :242-244
[3]   Molecular machines based on metal ion translocation [J].
Amendola, V ;
Fabbrizzi, L ;
Mangano, C ;
Pallavicini, P .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (06) :488-493
[4]   Phototransformation of Stilbene in van der Waals nanocapsules [J].
Ananchenko, GS ;
Udachin, KA ;
Ripmeester, JA ;
Perrier, T ;
Coleman, AW .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) :2441-2447
[5]  
[Anonymous], ANGEW CHEM
[6]   Improving the properties of organic dyes by molecular encapsulation [J].
Arunkumar, E ;
Forbes, CC ;
Smith, BD .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) :4051-4059
[7]   Resorcin[4]arene cavitand-based molecular switches [J].
Azov, VA ;
Beeby, A ;
Cacciarini, M ;
Cheetham, AG ;
Diederich, F ;
Frei, M ;
Gimzewski, JK ;
Gramlich, V ;
Hecht, B ;
Jaun, B ;
Latychevskaia, T ;
Lieb, A ;
Lill, Y ;
Marotti, F ;
Schlegel, A ;
Schlittler, RR ;
Skinner, PJ ;
Seiler, P ;
Yamakoshi, Y .
ADVANCED FUNCTIONAL MATERIALS, 2006, 16 (02) :147-156
[8]   Orientational preferences of aromatic guests in dimeric capsules of tetraurea calix[4]arenes -: MD and NMR studies [J].
Broda, Frank ;
Vysotsky, Myroslav O. ;
Boehmer, Volker ;
Thondorf, Iris .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2424-2432
[9]   Tuning the anion binding properties of calixpyrroles by means of p-nitrophenyl substituents at their meso-positions [J].
Bruno, Giuseppe ;
Cafeo, Grazia ;
Kohnke, Franz H. ;
Nicolo, Francesco .
TETRAHEDRON, 2007, 63 (40) :10003-10010
[10]   Syntheses, structures, and anion-binding properties of two novel calix[2]benzo[4]pyrroles [J].
Cafeo, Grazia ;
Kohnke, Franz H. ;
White, Andrew L. P. ;
Garozzo, Domenico ;
Messina, Angela .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) :649-656