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Chemically Fueled Assembly of Macrocycles Comprising Multiple Transient Bonds

preprint
submitted on 21.12.2019 and posted on 23.12.2019 by Mohammad Mosharraf Hossain, Joshua Atkinson, Scott Hartley
Dissipative (nonequilibrium) assembly powered by chemical fuels has great potential for the creation of new adaptive chemical systems. However, while molecular assembly at equilibrium is routinely used to prepare complex architectures from polyfunctional monomers, species formed out of equilibrium have, to this point, been structurally very simple. In most examples the fuel simply effects the formation of a single transient covalent bond. Here, we show that chemical fuels can assemble bifunctional components into macrocycles containing multiple transient bonds. Specifically, dicarboxylic acids give aqueous dianhydride macrocycles on treatment with a carbodiimide. The macrocycle is assembled efficiently as a consequence of both fuel-dependent and -independent mechanisms: it undergoes slower decomposition, building up as the fuel recycles the components, and is a favored product of the dynamic exchange of the anhydride bonds. These results create new possibilities for generating structurally sophisticated out-of-equilibrium species.

Funding

Dissipative assembly of carboxylic acid anhydrides for nonequilibrium systems chemistry

Basic Energy Sciences

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History

Email Address of Submitting Author

scott.hartley@miamioh.edu

Institution

Miami University

Country

USA

ORCID For Submitting Author

0000-0002-5997-6169

Declaration of Conflict of Interest

No conflict of interest

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in Angewandte Chemie International Edition

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