Jump to main content
Jump to site search

Issue 8, 2014
Previous Article Next Article

Effect of 1,3-adamantane bridging units within the surrounding macrocycle of squaraine rotaxanes

Author affiliations

Abstract

A systematic comparison of empty tetralactam macrocycles containing 1,3-benzenedicarboxamide, 2,6-pyridinedicarboxamide, and 1,3-adamantanedicarboxamide bridging units finds that macrocycles with adamantyl bridging units exhibit weaker non-covalent affinity for an encapsulated guest. In the case of interlocked squaraine rotaxanes with macrocycles containing phenylene sidewalls, the structural change induced by the adamantyl bridging units produces a more loosely held rotaxane co-conformation that diminishes the ability of the surrounding macrocycle to protect the encapsulated squaraine dye from attack by nucleophiles. In the case of squaraine rotaxanes with macrocycles containing anthracene sidewalls, there is no obvious change in rotaxane co-conformation. But there is a difference with the corresponding squaraine rotaxane endoperoxide, namely a significantly slower rate of cycloreversion and oxygen release. A series of molecular dynamics simulations provides reasons for the differences in co-conformational mobility. The overall result is a new set of structural strategies to control the chemical and photophysical properties of luminescent squaraine rotaxanes.

Graphical abstract: Effect of 1,3-adamantane bridging units within the surrounding macrocycle of squaraine rotaxanes

Back to tab navigation

Supplementary files

Publication details

The article was received on 05 May 2014, accepted on 18 Jun 2014 and first published on 19 Jun 2014


Article type: Paper
DOI: 10.1039/C4NJ00726C
Author version available: Download Author version (PDF)
Citation: New J. Chem., 2014,38, 3992-3998
  •   Request permissions

    Effect of 1,3-adamantane bridging units within the surrounding macrocycle of squaraine rotaxanes

    C. G. Collins, A. T. Johnson, R. D. Connell, R. A. Nelson, I. Murgu, A. G. Oliver and B. D. Smith, New J. Chem., 2014, 38, 3992
    DOI: 10.1039/C4NJ00726C

Search articles by author

Spotlight

Advertisements