TY - JOUR
T1 - Gelation landscape engineering using a multi-reaction supramolecular hydrogelator system
AU - Foster, Jamie S
AU - Zurek, Justyna M.
AU - Almeida, Nuno M. S.
AU - Hendrikson, Wouter E.
AU - le Sage, Vincent A. A.
AU - Lakshminarayanan, Vasudevan
AU - Thompson, Amber L
AU - Banerjee, Ragul
AU - Eelkema, Rienk
AU - Mulvana, Helen Elizabeth
AU - Paterson, Martin J
AU - van Esch, Jan H
AU - Lloyd, Gareth O.
PY - 2015/10/26
Y1 - 2015/10/26
N2 - 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.
AB - 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.
KW - gelation landscape engineering
KW - hydrogel materials
KW - hydrogelating molecules
KW - complex reaction network
U2 - 10.1021/jacs.5b06988
DO - 10.1021/jacs.5b06988
M3 - Article
SN - 0002-7863
VL - 137
SP - 14236
EP - 14239
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 45
ER -