Experimental and Theoretical Investigation of Structural, Spectroscopic, and Physicochemical Properties of Azobenzene-Based Compound

Abstract

Azobenzene-based compounds have recently attracted a lot of attention in innovative potential applications due to their photoresponsive properties and functions. Herein, we present a comprehensive theoretical and experimental investigation of the changes in the physical and chemical properties of an azobenzene-based compound under UV-light irradiation. In this context, first a novel monomer containing fluorine-substituted photoactive azobenzene and electroactive carbazole namely (E)-9-(4-(4-((4-(trifluoromethyl)phenyl)diazenyl)phenoxy)butyl)-9H-carbazole (coded as Cz-AzoCF₃) was synthesized. Theoretical studies were conducted using Density functional theory (DFT) and Time-Dependent DFT (TD-DFT) methods, utilizing the functionals of B3LYP and CAM-B3LYP (Becke-3–Lee–Yang–Parr) with the basis set of 6–31 G (d, p). The changes in structural, electronic, and vibrational properties induced by light were analyzed through a combination of theoretical and experimental approaches, utilizing techniques such as IR, NMR, and UV–vis spectroscopy. In conclusion, a high correlation was observed between experimental and calculated data. This remarkable agreement not only provides robust and guiding information on molecular design and characterization but also paves the way for new studies. From this perspective, experimental and theoretical studies are complementary to each other.