Three novel 1,2,3-triazole-fused compounds: Syntheses, structural and spectroscopic characterizations with molecular modeling

In this study, we report syntheses, structural and spectroscopic characterizations, and molecular modeling of three novel triazole fused compounds: 4-((4-methoxyphenoxy)methyl)-1-(4-methoxyphenyl)-1H-1,2,3-triazole, 1-(4-isopropylphenyl)-4-((4-methoxyphenoxy)methyl)-1H-1,2,3-triazole, and 1-(4-fluorophenyl)-4-((4-methoxyphenoxy)methyl)-1H-1,2,3-triazole. Their molecular structures and intermolecular interactions were elucidated using single-crystal X-ray crystallography. The compounds crystallize in the P-1 and P21/c space groups with weak C−H∙∙∙N and C-H∙∙∙O interactions. Hirshfeld surface analyses revealed the complex network of intermolecular interactions, determining that in all three compounds, an average of 13 % of the packing interactions were due to hydrogen bonds, and an average of 25 % were due to C-H···π interactions. Since the compounds differ from each other by only one substituent (methoxy, isopropyl, and fluorine) in their phenyl ring, their experimental infrared spectra were clarified by comparing them with the calculated ones. NMR spectroscopy was employed to examine the behavior of the compounds in solution. Conformational scans revealed that the energy differences between conformers are low, indicating potential conformations in which compounds could exist in solution. Nonlinear optical properties were calculated to evaluate the potential of the compounds for optical applications, particularly emphasizing the significantly larger values seen for two compounds compared to a reference compound. Finally, molecular electrostatic potential maps were generated to visualize the charge distribution and potential electrophilic and nucleophilic attack regions.