Switchable selectivity within a series of boronate esters for dynamic covalent exchange in nonaqueous solvents
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The reversible condensation–hydrolysis reactions of boronic acids have proven to be a highly useful class of thermodynamically controlled dynamic covalent process, enabling the construction of sugar sensors, stimuli-responsive materials, and complex covalent architectures. Yet, the common diol or diphenol coupling partners tend to produce relatively unstable condensation products, exhibit oxidative sensitivity, or offer limited options for expanding structural diversity. To address these drawbacks, we explore a series of coupling partners including non-diol salicylate and salicylamide derivatives, in combination with two boronic acids. In nonaqueous solvents, the condensation–hydrolysis equilibria are sensitive to the nature and concentration of Lewis bases, with equilibrium constants that can be tuned across at least five orders of magnitude. Furthermore, differential responses to base concentration can be exploited to create a switchable dynamic covalent system in which a boronic acid can be cycled between expressing each of two condensation products with high fidelity, in response to a simple chemical stimulus.
Borsley , S , Poss , G , Spicer , R L , Boudin , E & Kay , E R 2018 , ' Switchable selectivity within a series of boronate esters for dynamic covalent exchange in nonaqueous solvents ' , Supramolecular Chemistry , vol. Latest Articles . https://doi.org/10.1080/10610278.2018.1431393
© 2018 Informa UK Limited, trading as Taylor & Francis Group. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1080/10610278.2018.1431393
DescriptionThis work was supported by the EPSRC under Grants [EP/K016342/1 and EP/J500549/1]; the Leverhulme Trust under Grant [RPG-2015-042]; the ERASMUS+ scheme [mobility award to E.B.]; the Royal Society of Edinburgh and Scottish Government [Personal Fellowship to E.R.K.]; and the University of St Andrews.
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