4-Aryl-3,5-bis(arylethynyl)aryl-4H-1,2,4-triazoles. Multitask Skeleton as Self-Assembling Unit

 The synthesis of a series of 4-aryl-3,5-bis(arylethynyl)aryl-4H-1,2,4-triazoles derivatives is reported and the influence exerted by the peripheral substitution on the morphology of the aggregates generated from these 1,2,4-triazoles investigated by SEM imaging. The presence of paraffinic side chains results in long fibrillar supramolecular structures but unsubstituted triazoles self-assemble into thinner ribbons and needle-like aggregates. The crystals obtained from the methoxy-substituted triazoles 3i and 3j have been utilized to elaborate a model that contributes to justify the aggregation of the investigated 1,2,4 -triazoles in which the operation of arrays of C-H···π non-covalent interactions plays a significant role. The results presented herein demonstrate the ability of simple molecules to behave as multitask scaffolds showing different properties depending on the peripheral substitution. Thus, whilst 1,2,4-triazoles without long paraffinic side chains exhibit optical waveguiding behaviour, triazoles endowed with peripheral paraffinic side chains exhibit hexagonal columnar (Colh) mesomorphism.

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