A comprehensive investigation of the synthesis, spectral, DFT, and optical properties of a novel oxadiazolyl-pyrano[3,2-c]quinoline for photosensor applications

Abstract

The condensation reaction of pyranoquinoline-3-carbaoxldehyde 1 with benzohydraide afforded hydrazone 2 which upon oxidative cyclization yielded 6-ethyl-4‑hydroxy-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-pyrano[3,2-c]quinoline-2,5(6H)‑dione (EHPOPQ, 3). The DFT and B3LYP/6–311++G(d,p) basis set were used to compute the optimized molecular geometry. The global reactivity descriptors were examined and showed that hydrazone 2 exhibited high softness while aldehyde 1 had more electronegativity and high global electrophilicity. Subsequently, the reactive sites of the present compounds were located by tracing the MEP map. The GIAO method was used to calculate the 1H and 13C NMR. The current comprehensive investigation of the novel (EHPOPQ) reveals its significant potential for applications in nonlinear optics (NLO) and photovoltaics. Through high-level computational methods, EHPOPQ has an exceptionally high first hyperpolarizability (βtot) of 950 × 10−30 esu, which is substantially higher than that of the conventional NLO material urea. This high βtot value suggests that EHPOPQ could dramatically enhance the efficiency and performance of NLO devices such as frequency converters and optical modulators. In parallel, the detailed spectroscopic analysis of EHPOPQ's optical properties provided critical insights for photovoltaic applications. The optical band gap was measured to be 3.07 eV, indicating a direct band gap transition suitable for efficient light harvesting in solar cells. Additionally, dispersion parameters were carefully analyzed, which are essential for understanding the interaction of light with the material. The experimental characterization of EHPOPQ-based photovoltaic devices showed promising results. Current-voltage (J-V) measurements under varying illumination intensities revealed significant enhancements in the device's short-circuit current (from 1.2 µA to 4.3 µA) and open-circuit voltage (from 0.25 V to 0.47 V) as light intensity increased. These findings demonstrate the material's heightened photoresponsivity and suggest its potential as an efficient light conversion material for solar energy applications. These specific findings underline the importance of EHPOPQ in advancing both NLO and photovoltaic technologies, offering a pathway to more efficient and effective devices.