Journal
CHEMICAL SCIENCE
Volume 11, Issue 16, Pages 4239-4245Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc06481h
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Funding
- Air Force Office of Scientific Research [FA9550-19-1-0220]
- National Science Foundation (NSF) [CHE-1808143, CHE-1G10755, CHE-2003847]
- National Science Foundation CREST Center for Interface Design and Engineered Assembly of Low Dimensional Systems (IDEALS), NSF [HRD-1547830]
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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 O-1(2), 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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