5 years ago

CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes

CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes
Takashi Hayashi, Takashi Matsumoto, Yuta Miyazaki, Koji Oohora, Jennifer A. Wytko, Ayumu Ogawa, Christophe Kahlfuss, Jean Weiss
The synthesis of a porphyrin rotaxane by dipolar cycloaddition takes advantage of the ditopic character of a phenanthroline-strapped porphyrin. The success of the click reaction was conditioned by the presence of both a coordinatively unsaturated metal in the porphyrin and a copper(I) bound to the phenanthroline, pointing at a new “tandem active metal template” mechanism. All strapped in: Two metals cooperate for a click reaction leading to new [2]rotaxanes derived from a ditopic phenanthroline-strapped porphyrin. In addition to the copper active-template effect, coordination of the azide to the porphyrin's metal core is necessary to generate sterically constrained [2]rotaxanes.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702553

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