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

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Philp_2016_CS_Exploiting_CCBY.pdf (2.051Mb)
Date
01/04/2016
Author
Vidonne, Annick
Kosikova, Tamara
Philp, Douglas
Keywords
QD Chemistry
DAS
Metadata
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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 thread and the [2]rotaxane. The rate of [2]rotaxane formation is insensitive to the addition of preformed template, however, [2]rotaxane formation does show enhanced diastereoselectivity, most likely originating from its recognition- mediated formation through a binary reactive complex.
Citation
Vidonne , A , Kosikova , T & Philp , D 2016 , ' Exploiting recognition-mediated assembly and reactivity in [2]rotaxane formation ' , Chemical Science , vol. 7 , no. 4 , pp. 2592-2603 . https://doi.org/10.1039/C5SC04805B
Publication
Chemical Science
Status
Peer reviewed
DOI
https://doi.org/10.1039/C5SC04805B
ISSN
2041-6520
Type
Journal article
Rights
Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
Description
The authors thank EaStCHEM (Graduate Studentship to AV), EPSRC (Graduate Studentship to TK, Grant EP/K503162/1) and the University of St Andrews for financial support.
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  • University of St Andrews Research
URL
http://www.rsc.org/suppdata/c5/sc/c5sc04805b/c5sc04805b1.pdf
URI
http://hdl.handle.net/10023/8472

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