期刊
NATURE CHEMISTRY
卷 10, 期 7, 页码 696-703出版社
NATURE PORTFOLIO
DOI: 10.1038/s41557-018-0047-2
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资金
- US Air Force (AFOSR) [FA9550-15-1-0192, FA9550-014-1-0350]
- US Army Research Laboratory
- US Army Research Office [W911NF-16-1-0113]
Aqueous compatible supramolecular materials hold promise for applications in environmental remediation, energy harvesting and biomedicine. One remaining challenge is to actively select a target structure from a multitude of possible options, in response to chemical signals, while maintaining constant, physiological conditions. Here, we demonstrate the use of amino acids to actively decorate a self-assembling core molecule in situ, thereby controlling its amphiphilicity and consequent mode of assembly. The core molecule is the organic semiconductor naphthalene diimide, functionalized with D- and L- tyrosine methyl esters as competing reactive sites. In the presence of alpha-chymotrypsin and a selected encoding amino acid, kinetic competition between ester hydrolysis and amidation results in covalent or non-covalent amino acid incorporation, and variable supramolecular self-assembly pathways. Taking advantage of the semiconducting nature of the naphthalene diimide core, electronic wires could be formed and subsequently degraded, giving rise to temporally regulated electro-conductivity.
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