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Supramolecular chemistry under mechanochemical conditions: a small molecule template generated and integrated into a molecular-to-supramolecular and back-to-molecular cascade reaction
Journal article   Open access

Supramolecular chemistry under mechanochemical conditions: a small molecule template generated and integrated into a molecular-to-supramolecular and back-to-molecular cascade reaction

Shweta P Yelgaonkar, Dale C Swenson and Leonard R MacGillivray
Chemical science (Cambridge), Vol.11(13), pp.3569-3573
04/01/2020
DOI: 10.1039/c9sc05823k
PMCID: PMC8152585
PMID: 34109029
url
https://doi.org/10.1039/c9sc05823kView
Published (Version of record) Open Access

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Abstract

We describe the integration of a small-molecule hydrogen-bond-donor template into a cascade reaction that is comprised of a combination of molecular and supramolecular events. The cascade is performed mechanochemically and in the presence of μL amounts of water. The small-molecule template is generated (molecular) using water-assisted vortex grinding and is then used to assemble an alkene (supramolecular) to undergo an intermolecular [2 + 2] photodimerization reaction (molecular). The chemical cascade results in a cyclobutane photoproduct that we show serves as a building block of a hydrogen-bonded network with a topology that conforms to T-silica. Remarkably, the molecular–supramolecular–molecular chemical cascade occurs stepwise and entirely regioselectively within the continuous mechanochemical conditions employed. Mechanochemistry is applied to molecular and supramolecular chemistry to support a template-directed photochemical reaction.
 Chemistry

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