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

Abstract : The synthesis of a series of 4-aryl-3,5-bis(aryl-ethynyl) aryl-4H-1,2,4-triazoles derivatives is reported and the influence exerted by peripheral substitution on the morphology of the aggregates generated from these 1,2,4-triazoles is 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 methoxy-substituted triazoles have been utilised to elaborate a model that helps to justify aggregation of the investigated 1,2,4-triazoles, in which the operation of arrays of C-H center dot center dot center dot pi non-covalent interactions plays a significant role. The results presented herein demonstrate the ability of simple molecules to behave as multitasking scaffolds with different properties, depending on peripheral substitution. Thus, although 1,2,4-triazoles without long paraffinic side chains exhibit optical waveguiding behaviour, triazoles endowed with peripheral paraffinic side chains exhibit hexagonal columnar mesomorphism.
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M. Jesus Pastor, Iván Torres, Cristina Cebrian, Jose Ramon Carrillo, Angel Diaz-Ortiz, et al.. 4-Aryl-3,5-bis(arylethynyl)aryl-4H-1,2,4-triazoles: Multitasking Skeleton as a Self-Assembling Unit. Chemistry - A European Journal, Wiley-VCH Verlag, 2015, 21 (4), pp.1795-1802. ⟨10.1002/chem.201404243⟩. ⟨hal-01495198⟩



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