Issue 4, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2016,7, 2592-2603

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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