Issue 5, 2022

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
29 dec 2021
Accepted
19 jan 2022
First published
21 jan 2022

Org. Chem. Front., 2022,9, 1327-1335

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

Z. Lei, Q. Li, J. Sun, Z. Wang, H. Wang, Z. Li and D. Zhang, Org. Chem. Front., 2022, 9, 1327 DOI: 10.1039/D1QO01939B

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