A Chiral Quadruple-Stranded Helicate Cage for Enantioselective Recognition and Separation

被引:324
作者
Xuan, Weimin
Zhang, Mengni
Liu, Yan
Chen, Zhijie
Cui, Yong [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Technol, Shanghai 200240, Peoples R China
关键词
METAL-ORGANIC FRAMEWORKS; ASYMMETRIC CATALYSIS; SUPRAMOLECULAR HOST; RESOLUTION; COMPLEXES; GUEST; SALEN; REACTIVITY; SPACE; DNA;
D O I
10.1021/ja212132r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The self-assembly of enantiopure pyridyl-functionalized metallosalan units affords a homochiral helicate cage, [Zn8L4Cl8], in which the optical rotation of each ligand is increased by a factor of 10 upon coordination. The octanuclear cage featuring a chiral amphiphilic cavity exhibits enantioselective luminescence enhancement by amino acids in solution. The cage exists in two different crystalline polymorphic forms that possess porous structures built of helicate cages interconnected by 1D channels or pentahedral cages and have the ability to separate small racemic molecules by adsorption but with different enantioselectivities.
引用
收藏
页码:6904 / 6907
页数:4
相关论文
共 69 条
[21]  
Hof F, 2002, ANGEW CHEM INT EDIT, V41, P1488, DOI 10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO
[22]  
2-G
[23]  
Holst JR, 2010, NAT CHEM, V2, P915, DOI [10.1038/NCHEM.873, 10.1038/nchem.873]
[24]  
Hotze A.C.G., 2006, ANGEW CHEM INT EDIT, V45, P4839
[25]   Optically pure, water-stable metallo-helical 'flexicate' assemblies with antibiotic activity [J].
Howson, Suzanne E. ;
Bolhuis, Albert ;
Brabec, Viktor ;
Clarkson, Guy J. ;
Malina, Jaroslav ;
Rodger, Alison ;
Scott, Peter .
NATURE CHEMISTRY, 2012, 4 (01) :31-36
[26]   Synthesis of Molecular Nanostructures by Multicomponent Condensation Reactions in a Ball Mill [J].
Icli, Burcak ;
Christinat, Nicolas ;
Toennemann, Justus ;
Schuettler, Christian ;
Scopelliti, Rosario ;
Severin, Kay .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3154-+
[27]   Synthesis of Complementary Double-Stranded Helical Oligomers through Chiral and Achiral Amidinium-Carboxylate Salt Bridges and Chiral Amplification in Their Double-Helix Formation [J].
Ito, Hiroshi ;
Ikeda, Masato ;
Hasegawa, Takashi ;
Furusho, Yoshio ;
Yashima, Eiji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3419-3432
[28]   Stabilization of labile carbonyl addition intermediates by a synthetic receptor [J].
Iwasawa, Tetsuo ;
Hooley, Richard J. ;
Rebek, Julius, Jr. .
SCIENCE, 2007, 317 (5837) :493-496
[29]   Ligand reprogramming in dinuclear helicate complexes: A consequence of allosteric or electrostatic effects? [J].
Jeffery, John C. ;
Rice, Craig R. ;
Harding, Lindsay P. ;
Baylies, Christian J. ;
Riis-Johannessen, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) :5256-5271
[30]   Highly CO2-Selective Organic Molecular Cages: What Determines the CO2 Selectivity [J].
Jin, Yinghua ;
Voss, Bret A. ;
Jin, Athena ;
Long, Hai ;
Noble, Richard D. ;
Zhang, Wei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (17) :6650-6658