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题名: Switching on Supramolecular Catalysis via Cavity Mediation and Electrostatic Regulation
作者: Qiao, Yupu1; Zhang, Long2; Li, Jia1; Lin, Wei3; Wang, Zhenqiang1
关键词: calixarenes ; container molecules ; Knoevenagel condensation ; supramolecular catalysis ; tetraalkylammonium
刊名: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
发表日期: 2016-10-04
卷: 55, 期:41, 页:12778-12782
收录类别: SCI
英文摘要: Synthetic supercontainers constructed from divalent metal ions, carboxylate linkers, and sulfonylcalix[4]arene-based container precursors exhibit great promise as enzyme mimics that function in organic solvents. The capacity of these artificial hosts to catalyze Knoevenagel condensation can be switched on when the aldehyde substrate possesses a molecular size and shape matching the nanocavity of the supercontainers. In contrast, little reactivity is observed for other aldehydes that do not match the binding pocket. This substrate-dependent catalytic selectivity is attributed to the BrOnsted acidity of the metal-bound water molecules located inside the nanocavity, which is amplified when the size/shape of the aldehyde substrate fits the binding cavity. The electrostatic environment of the binding cavity and the BrOnsted acidity of the supercontainer can be further modulated using tetraalkylammonium-based regulators, leading to higher reactivity for the otherwise unreactive aldehydes.
语种: 英语
内容类型: 期刊论文
URI标识: http://ir.iccas.ac.cn/handle/121111/35519
Appears in Collections:分子识别与功能实验室_期刊论文

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作者单位: 1.Univ South Dakota, Dept Chem, Churchill Haines Labs, 414 East Clark St,Room 115, Vermillion, SD 57069 USA
2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
3.Univ Minnesota, Dept Chem, 207 Pleasant St SE, Minneapolis, MN 55455 USA
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