CuAAC in a Distal Pocket: Metal Active‐Template Synthesis of Strapped‐Porphyrin [2]Rotaxanes. Issue 55 (11th July 2017)

• Record Type: Journal Article
• Authors: Miyazaki, Yuta; Kahlfuss, Christophe; Ogawa, Ayumu; Matsumoto, Takashi; Wytko, Jennifer A.; Oohora, Koji; Hayashi, Takashi; Weiss, Jean
• Is Part Of: Chemistry. Volume 23:Issue 55(2017)
• Page Start: 13579
• Page End: 13582
• Publication Date: 2017-07-11
• Subjects: active template -- CuAAC -- cycloaddition -- porphyrinoid -- rotaxanes; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201702553
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : 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.