A supramolecular radical cation: folding-enhanced electrostatic effect for promoting radical-mediated oxidationElectronic supplementary information (ESI) available. See DOI: 10.1039/c8sc01434e

A supramolecular radical cation: folding-enhanced electrostatic effect for promoting... We report a supramolecular strategy to promote radical-mediated Fenton oxidation by the rational design of a folded hostguest complex based on cucurbit[8]uril (CB[8]). In the supramolecular complex between CB[8] and a derivative of 1,4-diketopyrrolo[3,4-c]pyrrole (DPP), the carbonyl groups of CB[8] and the DPP moiety are brought together through the formation of a folded conformation. In this way, the electrostatic effect of the carbonyl groups of CB[8] is fully applied to highly improve the reactivity of the DPP radical cation, which is the key intermediate of Fenton oxidation. As a result, the Fenton oxidation is extraordinarily accelerated by over 100 times. It is anticipated that this strategy could be applied to other radical reactions and enrich the field of supramolecular radical chemistry in radical polymerization, photocatalysis, and organic radical battery and holds potential in supramolecular catalysis and biocatalysis. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemical Science Royal Society of Chemistry

A supramolecular radical cation: folding-enhanced electrostatic effect for promoting radical-mediated oxidationElectronic supplementary information (ESI) available. See DOI: 10.1039/c8sc01434e

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Publisher
Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry
ISSN
2041-6520
D.O.I.
10.1039/c8sc01434e
Publisher site
See Article on Publisher Site

Abstract

We report a supramolecular strategy to promote radical-mediated Fenton oxidation by the rational design of a folded hostguest complex based on cucurbit[8]uril (CB[8]). In the supramolecular complex between CB[8] and a derivative of 1,4-diketopyrrolo[3,4-c]pyrrole (DPP), the carbonyl groups of CB[8] and the DPP moiety are brought together through the formation of a folded conformation. In this way, the electrostatic effect of the carbonyl groups of CB[8] is fully applied to highly improve the reactivity of the DPP radical cation, which is the key intermediate of Fenton oxidation. As a result, the Fenton oxidation is extraordinarily accelerated by over 100 times. It is anticipated that this strategy could be applied to other radical reactions and enrich the field of supramolecular radical chemistry in radical polymerization, photocatalysis, and organic radical battery and holds potential in supramolecular catalysis and biocatalysis.

Journal

Chemical ScienceRoyal Society of Chemistry

Published: May 16, 2018

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