Synthesis, characterization and DFT studies of fluorinated aryl derivatives: Electronic and optical responses

Abstract

The current study was designed to synthesize biaryls compounds viz; 2-(3,4-difluorophenyl) benzothiophene (DFPBT), 3-(3,4-difluorophenyl) quinoline (DFPQ) and 1-(3,4-difluorophenyl) naphthalene (DFPN) by means of Suzuki-Miyaura Pd(0)-catalyzed protocol. Different characterization techniques were used to evaluate the structure of desired synthesized compounds viz; H1NMR, C13NMR, FT-IR and UV–Vis analyses. Besides, DFT computations were carried out at B3LYP/6–311++ G(d, p) functional to gain an insight of key electronic properties of the synthesized compounds. The natural bonding orbital (NBO) analysis showed that molecules of these compounds should interact quite noticeably with each other in the solid phase and with polar solvent molecules. The FMO findings revealed that the ∆E value are in order; DFPN > DFPQ > DFPBT. Accordingly, DFPBT exhibited better NLO properties and possessed a slightly strong electron transfer potential than DFPQ and DFPN. A good harmony between experimental (296.4, 304.7 and 298.4 nm) and simulated (306, 305 and 298 nm) UV–Vis values was investigated in studied compounds. Furthermore, multiple functional (M062X, CAM-B3LYP, HF, M06, B3LPY, and LCBLYP) with 6–311++G(d, p) basis set were used to investigate the total dipole moment, hyperpolarizability βtot and average polarizability ⟨α⟩ values. The average polarizability ⟨α⟩ values of DFPBT, DFPQ and DFPN were 5.7, 5.7 and 5.5 times greater than urea i.e., ⟨α⟩=34.055 a.u, while, the βtot values were 5.8, 7.8 and 6.1 times more than the total values of urea. i.e., 90.527 a. u, respectively. These efficient behavior of NLO in synthesized compounds indicated the significant use of these compounds in optoelectronic devices.