A combined experimental and theoretical approach for structural, spectroscopic, NLO, NBO, thermal and photophysical studies of new fluorescent 5-amino-1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbonitrile using density functional theory

Abstract

We have synthesized a new fluorescent 5-amino-1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbonitrile containing 1,2,3-triazole moiety. The properties such as optimized structural parameters, spectroscopic (FT-IR and NMR), electronic and photophysical properties were investigated experimentally as well as theoretically using density functional theory calculations. The NMR spectrum was recorded in DMSO and the chemical shifts of hydrogen and carbon atoms were studied experimentally as well as theoretically. Electronic properties of molecule such as electrostatic surface potential analysis, charge analysis, the frontier molecular orbital analysis, total density of states, absorption-emission characteristics of molecule were studied. Nonlinear optical properties, reduced density gradient and natural bond orbital analysis were also studied. The first order hyperpolarizability (β0) was calculated and found to be six times higher than urea which makes it a potential NLO material. This new compound showed absorption spectra at 326–386 nm while emission band in range of 375–403 nm in different solvents. The ground state and excited state dipole moments were determined using solvatochromic methods and compared with theoretically calculated values. The interaction of synthesized compound with different solvents was also investigated using Kamlet-Taft and Catalan methods. The chemical reactivity indices and thermodynamic properties were also evaluated.