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Gelation-driven selection in dynamic covalent C[double bond, length as m-dash]C/C[double bond, length as m-dash]N exchange

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Abstract

Knoevenagel barbiturate derivatives bearing long alkyl chains were proven to form organogels in suitable solvents based on supramolecular interactions. Their reaction with imines allows for component exchange through C[double bond, length as m-dash]C/C[double bond, length as m-dash]N recombination. The effect of various parameters (solvents, chain length, and temperature) on the C[double bond, length as m-dash]C/C[double bond, length as m-dash]N exchange reaction has been studied. Mixing Knoevenagel compound K and imine I-16 in a 1 : 1 ratio generated a constitutional dynamic library containing the four constituents K, I-16, K′-16, and I′. The reversible exchange reaction was monitored by 1H-NMR, showing marked changes in the fractions of the four constituents on sol–gel interconversion as a function of temperature. The library composition changed from statistical distribution of the four constituents in the sol state to selective amplification of the gel forming K′-16 constituent together with that of its agonist I′. The process amounts to self-organization driven component selection in a constitutional dynamic organogel system undergoing gelation. This process displays up-regulation of the gel-forming constituent by component redistribution through reversible covalent connections.

Graphical abstract: Gelation-driven selection in dynamic covalent C [[double bond, length as m-dash]] C/C [[double bond, length as m-dash]] N exchange

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Publication details

The article was received on 25 Jul 2017, accepted on 15 Aug 2017 and first published on 06 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC02827J
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    Gelation-driven selection in dynamic covalent C[double bond, length as m-dash]C/C[double bond, length as m-dash]N exchange

    C. Liang, S. Kulchat, S. Jiang and J. Lehn, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC02827J

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