A Conjugated Covalent Template Strategy for All-Benzene Catenane Synthesis

Angew Chem Int Ed Engl. 2022 Sep 26;61(39):e202209449. doi: 10.1002/anie.202209449. Epub 2022 Aug 19.

Abstract

Mechanically interlocked molecules based on oligoparaphenylene-derived nanohoops, particularly those without heteroatoms, are synthetically challenging and topologically intriguing targets. Herein, a π-conjugated covalent template strategy based on azo group has been developed, which features dual intramolecular macrocyclizations directed by a tetra-substituted azobenzene core, followed by traceless removal of the azo linker. Employing this strategy, the efficient synthesis of a novel all-benzene [2]catenane consisting of meta-cycloparaphenylenes has been accomplished.

Keywords: Azobenzene; Catenane; Conjugated Covalent Template; Cycloparaphenylene; Interlocked Nanohoop.