Selective Photodimerization in a Cyclodextrin Metal-Organic Framework

被引:53
作者
Chen, Xiao-Yang [1 ]
Chen, Haoyuan [2 ]
Dordevic, Luka [1 ,3 ]
Guo, Qing-Hui [1 ]
Wu, Huang [1 ]
Wang, Yu [1 ]
Zhang, Long [1 ]
Jiao, Yang [1 ]
Cai, Kang [1 ]
Chen, Hongliang [1 ]
Stern, Charlotte L. [1 ]
Stupp, Samuel, I [1 ,3 ,4 ,5 ,6 ,7 ]
Snurr, Randall Q. [2 ]
Shen, Dengke [8 ]
Stoddart, J. Fraser [1 ,9 ,10 ,11 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
[2] Northwestern Univ, Dept Chem & Biol Engn, Evanston, IL 60208 USA
[3] Northwestern Univ, Ctr Bioinspired Energy Sci, Evanston, IL 60208 USA
[4] Northwestern Univ, Dept Mat Sci & Engn, Evanston, IL 60208 USA
[5] Northwestern Univ, Dept Biomed Engn, Evanston, IL 60208 USA
[6] Northwestern Univ, Dept Med, Chicago, IL 60611 USA
[7] Northwestern Univ, Simpson Querrey Inst, Chicago, IL 60611 USA
[8] Anhui Univ, Inst Phys Sci & Informat Technol, Hefei 230601, Peoples R China
[9] Univ New South Wales, Sch Chem, Sydney, NSW 2052, Australia
[10] Zhejiang Univ, Stoddart Inst Mol Sci, Dept Chem, Hangzhou 310027, Peoples R China
[11] ZJU Hangzhou Global Sci & Technol Innovat Ctr, Hangzhou 311215, Peoples R China
关键词
NONCOVALENT INTERACTIONS; MOLECULAR RECOGNITION; GAMMA-CYCLODEXTRIN; ENANTIODIFFERENTIATING PHOTOCYCLODIMERIZATION; ASYMMETRIC CATALYSIS; CARBON-DIOXIDE; CHEMISTRY; ENZYMES; BINDING; 2-ANTHRACENECARBOXYLATE;
D O I
10.1021/jacs.1c03277
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
For the most part, enzymes contain one active site wherein they catalyze in a serial manner chemical reactions between substrates both efficiently and rapidly. Imagine if a situation could be created within a chiral porous crystal containing trillions of active sites where substrates can reside in vast numbers before being converted in parallel into products. Here, we report how it is possible to incorporate 1-anthracenecarboxylate (1-AC(-)) as a substrate into a gamma-cyclodextrincontaining metal-organic framework (CD-MOF-1), where the metals are K+ cations, prior to carrying out [4+4] photodimerizations between pairs of substrate molecules, affording selectively one of four possible regioisomers. One of the high-yielding regioisomers exhibits optical activity as a result of the presence of an 8:1 ratio of the two enantiomers following separation by high-performance liquid chromatography. The solid-state superstructure of 1-anthracenecarboxylate potassium salt (1-ACK), which is co-crystallized with gamma-cyclodextrin, reveals that pairs of substrate molecules are not only packed inside tunnels between spherical cavities present in CD-MOF-1, but also stabilized.in addition to hydrogen-bonding to the C-2 and C-3 hydroxyl groups on the D-glucopyranosyl residues present in the gamma-cyclodextrin tori.by combinations of hydrophobic and electrostatic interactions between the carboxyl groups in 1-AC- and four K+ cations on the waistline between the two gamma-cyclodextrin tori in the tunnels. These non-covalent bonding interactions result in preferred co-conformations that account for the highly regio- and enantioselective [4+4] cycloaddition during photoirradiation. Theoretical calculations, in conjunction with crystallography, support the regio- and stereochemical outcome of the photodimerization.
引用
收藏
页码:9129 / 9139
页数:11
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