Jump to main content
Jump to site search

Issue 32, 2017
Previous Article Next Article

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

Author affiliations

Abstract

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 SN2 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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 05 Jul 2017, accepted on 25 Jul 2017 and first published on 25 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01642E
Citation: Org. Biomol. Chem., 2017,15, 6753-6763
  •   Request permissions

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

    V. Zanichelli, G. Ragazzon, G. Orlandini, M. Venturi, A. Credi, S. Silvi, A. Arduini and A. Secchi, Org. Biomol. Chem., 2017, 15, 6753
    DOI: 10.1039/C7OB01642E

Search articles by author

Spotlight

Advertisements