Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Abstract

The main purpose of this video is to show 6 reaction steps of a convergent synthesis and prepare a complex molecule containing up to three nonplanar polyaromatic units, which are two corannulene moieties and a racemic hexahelicene linking them. The compound described in this work is a good host for fullerenes. Several common organic reactions, such as free-radical reactions, C-C coupling or click chemistry, are employed demonstrating the versatility of functionalization that this compound can accept. All of these reactions work for planar aromatic molecules. With subtle modifications, it is possible to achieve similar results for nonplanar polyaromatic compounds.

Octapodal Corannulene Porphyrin-Based Assemblies: Allosteric Behavior in Fullerene Hosting

“…We developed a platinum-based system with two corannulene moieties, which was the first system capable of discriminating C 60 over C 70 (B); subsequently, Chen et al achieved outstanding discrimination ( K C 70 / K C 60 = 230:1) using the two-corannulene moiety system C . In contrast, systems bearing tris-corannulene clips, such as D and E, have not had the same success as systems bearing two corannulene units due to their lower ability to associate fullerenes. The lower binding constants observed for these tripodal systems ( K 1 = 1.50 × 10 3 M –1 (C 60 ) and K 1 = 2.19 × 10 3 M –1 (C 60 ) for D and E systems, respectively) seem to stem from their much greater flexibility, which favors self-interaction and consequently notably reduces their interaction with fullerenes.…”