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Efficient templation of pillar[6]arenes

par Lavendomme, Roy
Référence RSC Macrocyclic and Supramolecular Chemistry Meeting (MASC 2024) (December 2024: York, United Kingdom)
Publication Publié, 2024

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Résumé :

Pillararenes are pillar-shaped oligomeric macrocycles that attracted increasing attention since their discovery in 2008 for the development of applications in supramolecular chemistry and materials science. The pentameric pillar[5]arenes, the smallest members of this family, are the most accessible via a templation effect from the solvent of synthesis, 1,2-dichloroethane. The larger hexameric pillar[6]arenes are interesting due to their wider cavity that can fit larger guests, and their hexagonal shape that can benefit specific geometrical arrangements in materials. Unfortunately, the synthesis of pillar[6]arenes remains challenging due to suboptimal templation effects and/or solubility in solvents such as chloroform or chlorocyclohexane. Numerous reports of pillar[6]arenes synthesis methods demonstrate the significant effort of the scientific community to develop an efficient method but they are infamously plagued by reproducibility issues. A new family of templates for pillar[6]arenes is presented in this communication. These templates are Lewis adducts generated in situ from cheap reagents and allow for the formation of hexameric pillar[6]arenes with no trace of the smaller pentamer (Figure 1).