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Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles.

ABSTRACT: The ability of trans- and cis-1,2-glucopyranosyl and cyclohexyl ditriazoles, synthesized by CuAAC "click" chemistry, to form gels was studied, their physical properties determined, and the self-aggregation behavior investigated by SEM, X-ray, and EDC studies. The results revealed that self-assembly was driven mainly by ?-? stacking interactions, in addition to hydrogen bonding, with the aromatic rings adopting a high degree of parallelism, as seen in crystal packings and ECD data. Furthermore, ?-bromine interactions between the bromine atom of the aryl substituents and the triazole units might also contribute to an overall stabilization of the supramolecular aggregation of bis(4-bromophenyl)triazoles. The trans or cis spatial disposition of the triazole rings is highly important for gelation, with the cis configuration having higher propensity.

SUBMITTER: Tejera S

PROVIDER: S-EPMC6902786 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles.

Tejera Sara S Caniglia Giada G Dorta Rosa L RL Favero Andrea A González-Platas Javier J Vázquez Jesús T JT

Beilstein journal of organic chemistry 20191128

The ability of trans- and cis-1,2-glucopyranosyl and cyclohexyl ditriazoles, synthesized by CuAAC "click" chemistry, to form gels was studied, their physical properties determined, and the self-aggregation behavior investigated by SEM, X-ray, and EDC studies. The results revealed that self-assembly was driven mainly by π-π stacking interactions, in addition to hydrogen bonding, with the aromatic rings adopting a high degree of parallelism, as seen in crystal packings and ECD data. ...[more]

PMID: 31839834

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