Synthesis and Characterization of Pyranopyrazole derivatives as Potential Organic Nonlinear optical (NLO) Materials and Density Functional theory (DFT) studies

Abstract

In the current project fourteen derivatives of pyranopyrazole (AG.1-14) were formed and evaluated using analytical methods like ¹H NMR, ¹³CNMR IR spectra and mass spectrometry. It is stirring based, a base catalyzed method towards one step synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles by using pyrazolones as precursors. Using this one-pot condensation process between aryl aldehydes, malononitrile, and 3-Methyl-1-Phenyl pyrazoline-5-one, several pyranopyrazole derivatives were synthesised. In majority of reactions yields were between 90 to 100%. Furthermore, theoretical calculations were made for derivatives of Pyranopyrazole scaffolds applying DFT/B3LYP/6-31 + + G(d,p) technique along Gaussian 06 program. We observed the polarizability (?), hyperpolarizability (?), dipole moment (?), and HOMO-LUMO energies. Positions of HOMO and LUMO were located based on the HOMO-LUMO orbital image. Due to the important values of the molecular hyperpolarizabilities and well-microscopic NLO behavior, the experimental and theoretical results of the nonzero dipole moments, the polarization ability, and hyperpolarizabilities information suggest that such various types of molecules could be potential candidates for applications in various non-linear optical devices. Findings demonstrated that synthetic derivatives of pyranopyrazole scaffolds utilised as a non-linear optical substance in the organic light-emitting devices, and that energy gap of the molecule can be changed to create better NLO materials through altering the aldehydic phenyl rings' substituents.