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Title

4-aryl-3,5-bis(arylethynyl)aryl-4H-1,2,4-triazoles: Multitasking skeleton as a self-assembling unit

AuthorsBarberá, Joaquín; Prieto, Pilar ; Sánchez, Luis
KeywordsLiquid crystals
Optical waveguide
Self-assembly
Structure–activity relationships
Triazoles
Issue DateJan-2015
PublisherWiley-VCH
CitationChemistry - A European Journal 21(4): 1795-1802 (2015)
AbstractThe 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 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 CH⋅⋅⋅π 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.
Descriptionet al.
Publisher version (URL)http://dx.doi.org/10.1002/chem.201404243
URIhttp://hdl.handle.net/10261/121355
DOI10.1002/chem.201404243
ISSN0947-6539
E-ISSN1521-3765
Appears in Collections:(ICMA) Artículos
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