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Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane

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Author(s)

Tamara Kosikova, Nurul Izzaty Binti Hassan, David Bradford Cordes, Alexandra Martha Zoya Slawin, Douglas Philp

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Abstract

Within a small, interconnected reaction network, orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Rotaxane formation is governed by a central, hydrogen-bonding-mediated binding equilibrium between a macrocycle and a linear component, which associate to give a reactive pseudorotaxane. Both the pseudorotaxane and the linear component undergo irreversible, recognition-mediated 1,3-dipolar cycloaddition reactions with a stoppering maleimide group, forming rotaxane and thread, respectively. As a result of these orthogonal recognition-mediated processes, the rotaxane and thread can act as auto-catalytic templates for their own formation and also operate as crosscatalytic templates for each other. However, the interplay between the recognition and reaction processes in this reaction network results in the formation of undesirable pseudorotaxane complexes, causing thread formation to exceed rotaxane formation in the current experimental system. Nevertheless, in the absence of competitive macrocycle-binding sites, realization of a replicating network favoring formation of rotaxane is possible.
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Original languageEnglish
Pages (from-to)16074–16083
JournalJournal of the American Chemical Society
Volume137
Issue number51
Early online date16 Oct 2015
DOIs
Publication statusPublished - 30 Dec 2015

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