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A series of seven low molecular weight compounds containing triazole, pyridine-N-oxide, and one substituted aromatic ring linked together by heteroatoms containing spacers was synthesized by click chemistry reaction. The compounds were structurally characterized by FTIR, NMR, as well as single-crystal X-ray diffraction. Their morphologic, thermotropic, and photophysical properties were determined by dynamic light scattering, scanning electron microscopy, atomic force microscopy, polarized light microscopy, UV-vis, and photoluminescence spectroscopy. The triazole derivatives proved to have porous 3D supramolecular architectures determined by an extensive nonclassical hydrogen bonding network. They spontaneously crystallized into long nanofibers and exhibited typical molecular glass behavior, aggregation induced emission as well as crystallization induced emission enhancement. [ABSTRACT FROM AUTHOR]