Rational design and gas-phase characterization of molecular capsules by self-assembly of a symmetric hexasubstituted benzene with seven-membered lactams

被引:18
作者
Baillargeon, Pierre [1 ]
Dory, Yves L. [1 ]
机构
[1] Univ Sherbrooke, Inst Pharmacol, Dept Chim, Lab Synth Supramol, Sherbrooke, PQ J1H 5N4, Canada
关键词
D O I
10.1021/ja800734b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel very simple C-3-symmetric lactam has been rationally designed to self-assemble as dimers or larger platonic solid capsules. Its core flat benzene ring bears three seven-membered lactams, resulting I in tripod molecules that aggregate into robust tetrameric capsules. The self-assembly process was templated by tetraethylammonium cations and proven to be reversible by ESI spectroscopy in various solvents.
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收藏
页码:5640 / +
页数:3
相关论文
共 33 条
[1]   Longer guests drive the reversible assembly of hyperextended capsules [J].
Ajami, Dariush ;
Rebek, Julius, Jr. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9283-9286
[2]   Self-assembled hydrogen-bonded molecular cages of calix[6]arenetricarboxylic acid derivatives [J].
Arduini, A ;
Domiano, L ;
Ogliosi, L ;
Pochini, A ;
Secchi, A ;
Ungaro, R .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7866-7868
[3]   Mass spectrometric studies of non-covalent compounds: why supramolecular chemistry in the gas phase? [J].
Baytekin, Bilge ;
Baytekin, H. Tarik ;
Schalley, Christoph A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (15) :2825-2841
[4]  
Cave GWV, 2001, EUR J ORG CHEM, V2001, P3227
[5]  
Gerkensmeier T, 1999, EUR J ORG CHEM, V1999, P2257
[6]   Reversible encapsulation of disc-shaped guests by a synthetic, self-assembled host [J].
Grotzfeld, RM ;
Branda, N ;
Rebek, J .
SCIENCE, 1996, 271 (5248) :487-489
[7]   Pairwise selection of guests in a cylindrical molecular capsule of nanometre dimensions [J].
Heinz, T ;
Rudkevich, DM ;
Rebek, J .
NATURE, 1998, 394 (6695) :764-766
[8]  
Hof F, 2002, ANGEW CHEM INT EDIT, V41, P1488, DOI 10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO
[9]  
2-G
[10]   Selective binding and easy separation C70 by nanoscale self-assembled capsules [J].
Huerta, Elisa ;
Metselaar, Gerald A. ;
Fragoso, Alex ;
Santos, Eva ;
Bo, Carles ;
de Mendoza, Javier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :202-205