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Abstract
The C-alkylpyrogallol[4]arene macrocycles are known to form self-assembled dimeric and hexameric nanocapsules. Several conformations of alkyl-substituted pyrogallol[4]arenes have been found to be thermodynamically stable, with the most stable structures typically being a chair and cone. However, experimental evidence suggests that aryl-substituted pyrogallol[4]arenes exist in the chair conformation, implying that because for nanocapsule formation the cone is the necessary conformer of the subunits of these capsules, the chair must undergo some transition to the cone. To benchmark the intrinsic behavior of these systems, we here use quantum chemical calculations and molecular dynamics simulations to (1) investigate conformers of the R=H system and their solvent interactions to understand the structures and their relative stabilities, (2) explore interconversions between conformers, and (3) gain preliminary insight into the mechanism by which self-assembly of the nanocapsule occurs.
Acknowledgements
The computation for this work was performed on the high performance computing infrastructure provided by Research Computing Support Services and in part by the National Science Foundation under grant number CNS-1429294 at the University of Missouri, Columbia Mo.
Notes
* We are pleased to dedicate this article to Jerry L. Atwood in celebration of his contributions to supramolecular chemistry on his 75th birthday.