Exploiting recognition-mediated assembly and reactivity in rotaxane formation
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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 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 rotaxane. The rate of rotaxane formation is insensitive to the addition of preformed template, however, rotaxane formation does show enhanced diastereoselectivity, most likely originating from its recognition- mediated formation through a binary reactive complex.
Vidonne , A , Kosikova , T & Philp , D 2016 , ' Exploiting recognition-mediated assembly and reactivity in rotaxane formation ' Chemical Science , vol 7 , no. 4 , pp. 2592-2603 . DOI: 10.1039/C5SC04805B
Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
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.