Gelation landscape engineering using a multi-reaction supramolecular hydrogelator system

Foster, Jamie S and Zurek, Justyna M. and Almeida, Nuno M. S. and Hendrikson, Wouter E. and le Sage, Vincent A. A. and Lakshminarayanan, Vasudevan and Thompson, Amber L and Banerjee, Ragul and Eelkema, Rienk and Mulvana, Helen Elizabeth and Paterson, Martin J and van Esch, Jan H and Lloyd, Gareth O. (2015) Gelation landscape engineering using a multi-reaction supramolecular hydrogelator system. Journal of the American Chemical Society, 137 (45). pp. 14236-14239. ISSN 1520-5126 (https://doi.org/10.1021/jacs.5b06988)

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Abstract

Simultaneous control of the kinetics and thermodynamics of two different types of covalent chemistry allows pathway selectivity in the formation of hydrogelating molecules from a complex reaction network. This can lead to a range of hydrogel materials with vastly different properties, starting from a set of simple starting compounds and reaction conditions. Chemical reaction between a trialdehyde and the tuberculosis drug isoniazid can form one, two, or three hydrazone connectivity products, meaning kinetic gelation pathways can be addressed. Simultaneously, thermodynamics control the formation of either a keto or an enol tautomer of the products, again resulting in vastly different materials. Overall, this shows that careful navigation of a reaction landscape using both kinetic and thermodynamic selectivity can be used to control material selection from a complex reaction network.

ORCID iDs

Foster, Jamie S, Zurek, Justyna M., Almeida, Nuno M. S., Hendrikson, Wouter E., le Sage, Vincent A. A., Lakshminarayanan, Vasudevan, Thompson, Amber L, Banerjee, Ragul, Eelkema, Rienk, Mulvana, Helen Elizabeth ORCID logoORCID: https://orcid.org/0000-0002-5058-0299, Paterson, Martin J, van Esch, Jan H and Lloyd, Gareth O.;
CORE (COnnecting REpositories)