Open AccessGelation Landscape Engineering Using a Multi-Reaction Supramolecular Hydrogelator System
Author(s) -
Jamie S. Foster,
Justyna M. Żurek,
Nuno M. S. 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
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b06988
Subject(s) - chemistry , kinetic control , supramolecular chemistry , tautomer , molecule , hydrazone , computational chemistry , selectivity , combinatorial chemistry , organic chemistry , catalysis
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.
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