Loading…

Efficient active-template synthesis of calix[6]arene-based oriented pseudorotaxanes and rotaxanes

A substrate can modify its chemical features, including a change of its reactivity, as a consequence of non-covalent interactions upon inclusion within a molecular host. Since the rise of supramolecular chemistry, this phenomenon has stimulated the ingenuity of scientists to emulate the function of...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (32), p.6753-6763
Main Authors: Zanichelli, Valeria, Ragazzon, Giulio, Orlandini, Guido, Venturi, Margherita, Credi, Alberto, Silvi, Serena, Arduini, Arturo, Secchi, Andrea
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A substrate can modify its chemical features, including a change of its reactivity, as a consequence of non-covalent interactions upon inclusion within a molecular host. Since the rise of supramolecular chemistry, this phenomenon has stimulated the ingenuity of scientists to emulate the function of enzymes by designing supramolecular systems in which the energetics and selectivity of reactions can be manipulated through programmed host-guest interactions and/or steric confinement. In this paper we investigate how the engulfment of a positively charged pyridinium-based guest inside the π-rich cavity of a tris-(N-phenylureido)calix[6]arene host affects its reactivity towards a S 2 reaction. We found that the alkylation of complexed substrates leads to the formation of pseudorotaxanes and rotaxanes with faster kinetics and higher yields with respect to the standard procedures exploited so far. More importantly, the strategy described here expands the range of efficient synthetic routes for the formation of mechanically interlocked species with a strict control of the mutual orientation of their non-symmetric molecular components.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01642e