Open Access
Journal of Molecular Liquids, volume 376, pages 121489
Twisted intramolecular charge transfer, nonlinear optical, antibacterial activity, and DFT analysis of ultrasound processed (E)-N′-(4-isopropylbenzylidene)nicotinohydrazide
Publication type: Journal Article
Publication date: 2023-04-01
Journal:
Journal of Molecular Liquids
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 6
ISSN: 01677322, 18733166
Materials Chemistry
Electronic, Optical and Magnetic Materials
Physical and Theoretical Chemistry
Spectroscopy
Atomic and Molecular Physics, and Optics
Condensed Matter Physics
Abstract
Hydrazones have attracted considerable interest for their antimicrobial and nonlinear optical (NLO) applications. In the present work, a new hydrazone (E)-N′-(4-isopropylbenzylidene)nicotinohydrazide (INH) was synthesized by a condensation reaction of cuminaldehyde with nicotinic hydrazide via ultrasonication. The hydrazone was characterized by FT-IR spectroscopy, mass spectrometry, NMR (1H, 13C, HOMO-COSY, HSQC, and DEPT-135), elemental analysis, and FESEM analyses. Phase-pure and non-existent isomorphic phase transition in INH was demonstrated by X-ray diffraction and thermogravimetric analysis. The absorption maximum of INH in an aqueous solution was red-shifted compared to that of the reactant molecules, indicating that the CN bond formation efficiently enhances the resonance interaction towards the pyridine ring. Fluorescence emission of INH at a shorter wavelength is caused by a locally excited state. A longer wavelength band is caused by intramolecular proton transfer in nonpolar/aprotic solvents, while it is caused by TICT emission in protic solvents. The direct and indirect bandgaps of the INH crystals were assessed using Tauc plots and the Kubelka–Munk algorithm. The efficacy of INH for the inactivation of E. coli and B. subtilis were examined through a plate colony counting assay, and the inactivation was 62.7 ± 0.2 % and 98.3 ± 0.4 %, respectively. The geometrical structure, Mulliken, MEP surface, and electronic properties of INH are theoretically optimized using density functional theory (DFT) at the B3LYP/6-31G(d,p) level and showed good concurrence with the experimentally defined structure. The INH displays higher NLO properties compared to urea as a reference, as determined by molecular hyperpolarizability analysis. The frontier molecular orbitals and global reactivity descriptors showed that INH is more reactive and reasonably stable.
Top-30
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1 publication, 10%
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1 publication, 10%
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Citations by publishers
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7
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Elsevier
7 publications, 70%
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Wiley
2 publications, 20%
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 10%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Meenatchi V., Cheng L., Han S. S. Twisted intramolecular charge transfer, nonlinear optical, antibacterial activity, and DFT analysis of ultrasound processed (E)-N′-(4-isopropylbenzylidene)nicotinohydrazide // Journal of Molecular Liquids. 2023. Vol. 376. p. 121489.
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Meenatchi V., Cheng L., Han S. S. Twisted intramolecular charge transfer, nonlinear optical, antibacterial activity, and DFT analysis of ultrasound processed (E)-N′-(4-isopropylbenzylidene)nicotinohydrazide // Journal of Molecular Liquids. 2023. Vol. 376. p. 121489.
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TY - JOUR
DO - 10.1016/j.molliq.2023.121489
UR - https://doi.org/10.1016/j.molliq.2023.121489
TI - Twisted intramolecular charge transfer, nonlinear optical, antibacterial activity, and DFT analysis of ultrasound processed (E)-N′-(4-isopropylbenzylidene)nicotinohydrazide
T2 - Journal of Molecular Liquids
AU - Meenatchi, Venkatasamy
AU - Cheng, L.
AU - Han, Sung Soo
PY - 2023
DA - 2023/04/01 00:00:00
PB - Elsevier
SP - 121489
VL - 376
SN - 0167-7322
SN - 1873-3166
ER -
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@article{2023_Meenatchi,
author = {Venkatasamy Meenatchi and L. Cheng and Sung Soo Han},
title = {Twisted intramolecular charge transfer, nonlinear optical, antibacterial activity, and DFT analysis of ultrasound processed (E)-N′-(4-isopropylbenzylidene)nicotinohydrazide},
journal = {Journal of Molecular Liquids},
year = {2023},
volume = {376},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/j.molliq.2023.121489},
pages = {121489},
doi = {10.1016/j.molliq.2023.121489}
}