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Issue 8, 2019
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Using reversible non-covalent and covalent bonds to create assemblies and equilibrating molecular networks that survive 5 molar urea

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Abstract

The limits of self-assembly and host–guest chemistry in water solutions containing competitive solutes are largely unexplored. We report here a new family of self-assembling systems that are stitched together at two levels by reversible hydrazone bonds and by non-covalent self-assembly in strongly denaturing conditions. Three different hydrazides of various charge and hydrophobicity are combined with an aldehyde-containing calixarene, and each system spontaneously forms AB hydrazones that subsequently self-assemble into four-component (AB)2 structures in water. The assemblies display varying responses to added NaCl and/or urea. The most robust assembly survives completely intact in solution up to 5 M urea. We also combine the aldehyde calixarene with two different hydrazides in the same tube to create complex, competitive dynamic libraries. We report experiments in which the composition of the dynamic equilibrating library is under the control of self-assembly, allowing the systems to choose the components that form the most stable assemblies under a variety of competitive solutions conditions. These dynamic networks of equilibrating molecules maintain remarkably similar equilibrium positions under widely varying concentrations of urea and NaCl.

Graphical abstract: Using reversible non-covalent and covalent bonds to create assemblies and equilibrating molecular networks that survive 5 molar urea

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Article information


Submitted
21 Nov 2018
Accepted
23 Jan 2019
First published
23 Jan 2019

Org. Biomol. Chem., 2019,17, 2081-2086
Article type
Communication

Using reversible non-covalent and covalent bonds to create assemblies and equilibrating molecular networks that survive 5 molar urea

M. A. Beatty, A. T. Pye, A. Shaurya, B. Kim, A. J. Selinger and F. Hof, Org. Biomol. Chem., 2019, 17, 2081
DOI: 10.1039/C8OB02909A

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