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A cucurbit[8]uril-stabilized 3D charge transfer supramolecular polymer with a remarkable confinement effect for enhanced photocatalytic proton reduction and thioether oxidation†
Zhuo Lei,Qian Li,Jian-Da Sun,Ze-Kun Wang,Hui Wang,Zhan-Ting Li,Dan-Wei Zhang
Organic Chemistry Frontiers Pub Date : 01/21/2022 00:00:00 , DOI:10.1039/D1QO01939B
Abstract

A highly water-soluble tetrahedral compound T1 that contains one tetraphenylmethane core and four 2-oxynaphthelene-CH2-4,4′-bipyridinium (NP-CH2-DIPY) side arms has been prepared. Control experiments reveal that NP-CH2-BIPY undergoes antiparallel dimerization which is stabilized by two charge transfer interactions with NP as an electron-rich donor and BIPY as an electron-deficient acceptor. This binding motif drives T1 to aggregate into a nanoscale supramolecular polymer SP in water. Adding 2 equivalents of cucurbit[8]uril to the solution of SP leads to the formation of a more stable three dimensional supramolecular polymer CBSP through a 2 + 2 binding motif in which two CB[8] rings encapsulate one charge transfer complex formed by the antiparallel NP-CH2-DIPY dimer. As a water soluble porous supramolecular polymer, CBSP exhibits a remarkable confinement effect for visible light-induced proton reduction to produce hydrogen and L-methionine thioether oxidation to the corresponding sulfoxide derivative in water.

Graphical abstract: A cucurbit[8]uril-stabilized 3D charge transfer supramolecular polymer with a remarkable confinement effect for enhanced photocatalytic proton reduction and thioether oxidation
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