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Issue 4, 2016
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Exploiting recognition-mediated assembly and reactivity in [2]rotaxane formation

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Abstract

A small molecular reaction network exploits recognition-mediated reactive processes in order to drive the assembly and formation of both a self-replicating linear template (thread) and a [2]rotaxane, in which the linear template is encircled by a diamide macrocycle. Complementary recognition sites, placed at strategic positions on the reactive building blocks, drive these assembly and replication processes. Template-instructed experiments show that the thread is capable of efficient self-replication and that no cross-catalytic relationships exist between the thread and the [2]rotaxane. The rate of [2]rotaxane formation is insensitive to the addition of a preformed template, however, [2]rotaxane formation does show enhanced diastereoselectivity, most likely originating from its recognition-mediated formation through a ternary reactive complex.

Graphical abstract: Exploiting recognition-mediated assembly and reactivity in [2]rotaxane formation

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Supplementary files

Article information


Submitted
11 Dec 2015
Accepted
15 Jan 2016
First published
15 Jan 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 2592-2603
Article type
Edge Article

Exploiting recognition-mediated assembly and reactivity in [2]rotaxane formation

A. Vidonne, T. Kosikova and D. Philp, Chem. Sci., 2016, 7, 2592
DOI: 10.1039/C5SC04805B

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