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

Ngo, Huynh Thien; Lewis, James E. M.; Payne, Daniel T.; D’Souza, Francis; Hill, Jonathan P.; Ariga, Katsuhiko; Yoshikawa, Genki and Goldup, Stephen M. (2020). Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores. Chemical Communications, 56(54) pp. 7447–7450.

DOI: https://doi.org/10.1039/c9cc09681g

Abstract

The high yielding Cu^I-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu^I 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 Cu^I-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.

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