Gelation Landscape Engineering Using a Multi-Reaction Supramolecular Hydrogelator System

Jamie Foster, Justyna Marlena Zurek, Nuno Miguel da Silva Almeida, Wouter E. Hendriksen, Vincent A. A. le Sage, Vasudevan Lakshminarayanan, Amber L. Thompson, Rahul Banerjee, Rienk Eelkema, Helen Mulvana, Martin J Paterson, Jan H. van Esch, Gareth O Lloyd

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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 froma complex reaction network.
Original languageEnglish
Pages (from-to)14236–14239
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number45
Early online date26 Oct 2015
DOIs
Publication statusPublished - 18 Nov 2015

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    Foster, J., Zurek, J. M., Almeida, N. M. D. S., Hendriksen, W. E., le Sage, V. A. A., Lakshminarayanan, V., Thompson, A. L., Banerjee, R., Eelkema, R., Mulvana, H., Paterson, M. J., van Esch, J. H., & Lloyd, G. O. (2015). Gelation Landscape Engineering Using a Multi-Reaction Supramolecular Hydrogelator System. Journal of the American Chemical Society, 137(45), 14236–14239. https://doi.org/10.1021/jacs.5b06988