Issue 54, 2020

Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

Abstract

The high yielding CuI-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the CuI catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a “sacrificial rotaxane” strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing CuI-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.

Graphical abstract: Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

Supplementary files

Article information

Article type
Communication
Submitted
13 Dec 2019
Accepted
26 May 2020
First published
04 Jun 2020

Chem. Commun., 2020,56, 7447-7450

Author version available

Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

H. T. Ngo, J. E. M. Lewis, D. T. Payne, F. D’Souza, J. P. Hill, K. Ariga, G. Yoshikawa and S. M. Goldup, Chem. Commun., 2020, 56, 7447 DOI: 10.1039/C9CC09681G

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