Synthesis, characterization and self-assembly of novel fluorescent alkoxy-substituted 1, 4-diarylated 1, 2, 3-triazoles organogelators

Abstract

Novel organogelators based on fluorescent alkoxy-substituted 1,4-diarylated 1, 2, 3-triazoles are reported. The findings monitored in the current study promoted the development of inventive compacted supramolecular architectures generated by self-assembly of the prepared triazole-based organogelators. The synthesis, characterization and gelation properties of the current novel alkoxy-substituted 1,4-diarylated 1, 2, 3-triazole arms were described. The synthesis procedures were accomplished by using Cu-catalyzed azide-alkyne cycloaddition (CuAAC) of alkoxy-substituted aryl azide with aryl bearing terminal alkyne subtituents and alkoxy chains of different lengths. The alkoxy-substituted of 1, 4-diarylated 1, 2, 3-triazole derivatives bearing different alkoxy chains were characterized by FTIR, 1H/13C NMR, and elemental analysis. The 1, 4-diarylated 1, 2, 3-triazoles with longer alkoxy terminal groups demonstrated improved gelation properties compared to those with shorter alkoxy terminals. The morphologies of the self-assembled alkoxy-substituted 1, 4-diarylated 1, 2, 3-triazoles were investigated using scanning electron microscopy (SEM), which demonstrated arrangements of highly ordered nanofibers, forced by π-stacks and van der Waals interactions. The antibacterial activity and cytotoxicity of the newly synthesized triazoles was investigated to verify the potential use of the present triazole gelators for a variety of applications, such as drug delivery.

Keywords

• CuAAC
• 1;2;3-Triazole
• Fluorescence
• Self-assembly
• Nanofibers