Visible-light photooxidation in water by 1O2-generating supramolecular hydrogels

Sankarsan Biswas; Mohit Kumar; Andrew M. Levine; Ian Jimenez; Rein V. Ulijn; Adam B. Braunschweig

doi:10.1039/C9SC06481H

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Visible-light photooxidation in water by ¹O₂-generating supramolecular hydrogels†

Sankarsan Biswas,

^abc Mohit Kumar,

^ab Andrew M. Levine,

^abc Ian Jimenez,^ae Rein V. Ulijn

*^abcd and Adam B. Braunschweig

*^abcd

Author affiliations

* Corresponding authors

^a Advanced Science Research Center, Graduate Center, City University of New York, 85 St. Nicholas Terrace, New York, NY 10031, USA
E-mail: abraunschweig@gc.cuny.edu

^b Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10065, USA

^c PhD Program in Chemistry, Graduate Center, City University of New York, New York, NY 10016, USA

^d PhD Program in Biochemistry, Graduate Center, City University of New York, New York, NY 10016, USA

^e The High School for Math, Science, and Engineering, The City College of New York, 240 Convent Avenue, New York, NY 10031, USA

Abstract

We report supramolecular photocatalytic hydrogels, produced by the enzymatically driven self-assembly of low molecular weight gelators (LMWGs). These LMWG precursors are composed of the organic chromophore diketopyrrolopyrrole (DPP), which is bi-functionalized with a series of amino acid (Phe, Tyr, Leu) methyl esters. In situ enzymatic hydrolysis of these photoactive precursors results in supramolecular hydrogels that provide a high density of photocatalytic sites. Under visible light irradiation these hydrophobic fibers recruit the reaction substrates and also produce ¹O₂, which is used here for the photooxidation of thioanisole (aromatic substrate) and cyclohexyl methyl sulfide (aliphatic substrate), with yields as high as 100% and without over-oxidation. Finally, we demonstrate that the nature of the amino acids in the LWMGs has a central role in dictating J-/H-/mixed state aggregates, gel properties, and, hence, the efficiency of chemoselective photooxidation of thioanisole and cyclohexyl methyl sulfide inside these hydrogels.

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Article information

DOI: https://doi.org/10.1039/C9SC06481H
Article type: Edge Article
Submitted: 20 Dec 2019
Accepted: 01 Apr 2020
First published: 03 Apr 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2020,11, 4239-4245

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Visible-light photooxidation in water by ¹O₂-generating supramolecular hydrogels

S. Biswas, M. Kumar, A. M. Levine, I. Jimenez, R. V. Ulijn and A. B. Braunschweig, Chem. Sci., 2020, 11, 4239 DOI: 10.1039/C9SC06481H

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