title: 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(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 C-H⋅⋅⋅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.
authors.affiliation: Departamento de Química Inorgánica, Orgánica y Bioquímica, Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La Mancha, 13071 Ciudad Real (Spain).
authors.forename: M Jesús
authors.initials: MJ
authors.lastname: Pastor
authors.forename: Iván
authors.initials: I
authors.lastname: Torres
authors.forename: Cristina
authors.initials: C
authors.lastname: Cebrián
authors.forename: José Ramón
authors.initials: JR
authors.lastname: Carrillo
authors.forename: Ángel
authors.initials: Á
authors.lastname: Díaz-Ortiz
authors.forename: Emilio
authors.initials: E
authors.lastname: Matesanz
authors.forename: Julia
authors.initials: J
authors.lastname: Buendía
authors.forename: Fátima
authors.initials: F
authors.lastname: García
authors.forename: Joaquín
authors.initials: J
authors.lastname: Barberá
authors.forename: Pilar
authors.initials: P
authors.lastname: Prieto
authors.forename: Luis
authors.initials: L
authors.lastname: Sánchez
keywords: liquid crystals; optical waveguide; self-assembly; structure-activity relationships; triazoles