Longer guests drive the reversible assembly of hyperextended capsules

被引:53
作者
Ajami, Dariush [1 ]
Rebek, Julius, Jr. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
extended capsules; host-guest systems; molecular recognition; reversible encapsulation; self-assembly;
D O I
10.1002/anie.200702245
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Hyperextension: A hydrogen-bonded, dimeric capsule can be expanded with four, eight, or twelve glycoluril spacers (see picture) that increase the cavity's volume by up to 530 Å3 and its length by up to 21 Å. The extended assemblies are chiral and encapsulate a variety of normal alkanes. The expanded capsules suggest that increasingly complex capsules may emerge from other spacers with hydrogen-bonding capabilities and curved surfaces. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9283 / 9286
页数:4
相关论文
共 33 条
[1]   Expanded capsules with reversibly added spacers [J].
Ajami, D ;
Rebek, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (16) :5314-5315
[2]  
AJAMI D, 2007, ANGEW CHEM, V119, P246
[3]   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
[4]   Coiled molecules in spring loaded devices [J].
Ajami, Dariush ;
Rebek, Julius, Jr. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) :15038-15039
[5]   Experimental and computational probes of the space in a self-assembled capsule [J].
Ajami, Dariush ;
Iwasawa, Tetsuo ;
Rebek, Julius, Jr. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (24) :8934-8936
[6]  
[Anonymous], ANGEW CHEM
[7]   Selectivity in an encapsulated cycloaddition reaction [J].
Chen, J ;
Rebek, J .
ORGANIC LETTERS, 2002, 4 (03) :327-329
[8]   Diffusion NMR spectroscopy in supramolecular and combinatorial chemistry: An old parameter - New insights [J].
Cohen, Y ;
Avram, L ;
Frish, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :520-554
[9]   Molecular recognition and stabilization of iminium ions in water [J].
Dong, Vy M. ;
Fiedler, Dorothea ;
Carl, Barbara ;
Bergman, Robert G. ;
Raymond, Kenneth N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (45) :14464-14465
[10]   Supramolecular catalysis of a unimolecular transformation: Aza-cope rearrangement within a self-assembled host [J].
Fiedler, D ;
Bergman, RG ;
Raymond, KN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (48) :6748-6751