Cuminaldehyde-3-hydroxy-2-napthoichydrazone: Synthesis, effect of solvents, nonlinear optical activity, antioxidant activity, antimicrobial activity, and DFT analysis.

[Display omitted] • New essential oil component derived hydrazone (EOCD) was synthesized efficiently using ultrasonication. • In all solvents, EOCD exhibited dual emissions. • Large Stokes shifted emission originated because of twisted intramolecular charge transfer. • EOCD showed higher NLO, antioxidant, and antibacterial properties. • DFT results were in good agreement with the experimental deductions. Hydrazones derived from essential oil components have attracted considerable interest because of their antimicrobial, antioxidant, and nonlinear optical applications. In the present work, a new essential oil component derivative (EOCD), cuminaldehyde-3-hydroxy-2-napthoichydrazone (CHNH), was synthesized. EOCD was characterized by Fourier transform infrared spectroscopy, mass spectrometry, nuclear magnetic resonance (1H and 13C) spectroscopy, elemental analysis, ultraviolet–visible absorption spectroscopy, and field-emission scanning electron microscopy. Thermogravimetric analysis and X-ray diffraction showed a higher stability, phase-pure, and non-existent isomorphic phase transition in EOCD. Solvent studies indicated that the normal emission band was caused by the locally excited state and the large Stokes shifted emission originated because of the twisted intramolecular charge transfer. The EOCD possessed higher direct and indirect band gap energies of 3.05 eV and 2.90 eV respectively, as determined by the Kubelka–Munk algorithm. The outcomes of frontier molecular orbitals, global reactivity descriptors, Mulliken, and molecular electrostatic potential surface by density functional theory calculations revealed high intramolecular charge transfer, good realistic stability, and high reactiveness of EOCD. The hydrazone EOCD exhibited higher hyperpolarizability (18.248 × 10−30 esu) in comparison to urea. Antioxidant test results indicated that EOCD showed significant antioxidant activity (p < 0.05), as determined by the DPPH radical scavenging assay. The newly synthesized EOCD showed no antifungal activity against Aspergillus flavus. Additionally, the EOCD showed good antibacterial activity against Escherichia coli and Bacillus subtilis. [ABSTRACT FROM AUTHOR]