Synthesis and spectral characterization of acetophenone thiosemicarbazone—A nonlinear optical material

Santhakumari, R.; Ramamurthi, K.; Vasuki, G.; Yamin, Bohari Mohd.; Bhagavannarayana, G.

doi:10.1016/j.saa.2010.03.030

Cited by 52 publications

(11 citation statements)

References 17 publications

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“…Complex 6 shows decomposition of 88.15% (calcd 89.52%) from 240 to 563 °C with an exothermic peak at 553 °C, leaving a residue of CuO around 11.85% (calcd 11.28%) above 600 °C, whereas complex 8 decomposes around 88.58% (calcd 89.09%) from 270 to 545 °C with an exothermic peak at 494 °C, leaving a residue around 11.42% (calcd 10.90%) of CuO above 600 °C. The thermogravimetric data clearly support the higher thermal stability of the synthesized complexes when compared to the starting ligands …”

Section: Resultssupporting

confidence: 54%

“…Complex 6 shows decomposition of 88.15% (calcd 89.52%) from 240 to 563 °C with an exothermic peak at 553 °C, leaving a residue of CuO around 11.85% (calcd 11.28%) above 600 °C, whereas The thermogravimetric data clearly support the higher thermal stability of the synthesized complexes when compared to the starting ligands. 39 ■ BIOLOGICAL INVESTIGATION Stability of the Complexes. One of the important steps in the drug approval process is stability testing, which ensures the maintenance of the product quality, safety, and efficacy throughout the shelf life and is considered as a prerequisite for the acceptance and approval of any pharmaceutical product.…”

Section: Chemical Research In Toxicologymentioning

confidence: 99%

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Biocompatibility, in Vitro Antiproliferative, and in Silico EGFR/VEGFR2 Studies of Heteroleptic Metal(II) Complexes of Thiosemicarbazones and Naproxen

Bharathi

Mahendiran

Raju

et al. 2019

Chem. Res. Toxicol.

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Eight heteroleptic nickel(II) and copper(II) complexes of the type [M(L 1−4 )(nap) 2 ] (1−8), where L 1−4 = 2-(1-(4-substitutedphenyl)ethylidene)hydrazinecarbothioamide, nap = naproxen, and M = Ni(II) or Cu(II), have been synthesized and characterized. UV−vis and EPR spectral studies showed distorted octahedral geometry around metal(II) ions. The cyclic voltammogram of complexes 1−8 displayed an irreversible one-electron transfer process in the cathodic region (E pc = −0.66 to −1.43 V), and nickel(II) complexes 1−4 displayed an irreversible one-electron oxidation process in the anodic region (E pa = 0.75 to 1.10 V). The obtained magnetic moment values (1.82−1.93 μ B ) for copper(II) complexes 5−8 indicate distortion from octahedral geometry, which is further supported by EPR studies. The geometry of the complexes is retained in both solid and solution phases as evidenced from UV−vis and EPR studies. All the complexes showed stability for almost 72 h in biologically relevant solutions. The reducing ability of the copper(II) complexes in the presence of ascorbic acid was analyzed by UV−vis and cyclic voltammetry techniques, which indicates the reduction of the copper(II) to a copper(I) center, and possible interaction within the cells. An in vitro antiproliferative study revealed the nontoxic nature of complexes to normal human dermal fibroblast (NHDF) up to a concentration of 100 ng/mL. The antiproliferative activity of the complexes was tested against three cancerous (human breast adenocarcinoma (MCF-7), hepatoma (HepG2), and lung (A549)) cell lines using MTT reduction assay, which showed enhanced activity for complexes 4 and 8 containing the hydrophobic substituent. Apoptotic and cellular uptake studies showed that complex 8 is readily taken up by HepG2 cell lines and induces ROS-mediated mitochondrial and caspase-dependent apoptosis. In silico studies indicated hydrogen bonding, hydrophobic, and π-pair (π−π, π−σ, and π−cation) interactions between the complexes and EGFR/VEGFR2 kinase receptors.

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Section: Resultssupporting

confidence: 54%

“…Complex 6 shows decomposition of 88.15% (calcd 89.52%) from 240 to 563 °C with an exothermic peak at 553 °C, leaving a residue of CuO around 11.85% (calcd 11.28%) above 600 °C, whereas The thermogravimetric data clearly support the higher thermal stability of the synthesized complexes when compared to the starting ligands. 39 ■ BIOLOGICAL INVESTIGATION Stability of the Complexes. One of the important steps in the drug approval process is stability testing, which ensures the maintenance of the product quality, safety, and efficacy throughout the shelf life and is considered as a prerequisite for the acceptance and approval of any pharmaceutical product.…”

Section: Chemical Research In Toxicologymentioning

confidence: 99%

Biocompatibility, in Vitro Antiproliferative, and in Silico EGFR/VEGFR2 Studies of Heteroleptic Metal(II) Complexes of Thiosemicarbazones and Naproxen

Bharathi

Mahendiran

Raju

et al. 2019

Chem. Res. Toxicol.

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“…In this perspective, we chose 4-methoxyacetophenone thiosemicarbazone (MAPTSC) as our organic push-pull system because thiosemicarbazones and their metal complexes are notable materials for SHG and, as such, are highly applicable in the field of nonlinear optics [16]. The extensive electron delocalization in the thiosemicarbazone (TSC) moiety greatly improves the SHG efficiency of free TSC ligands and their metal complexes [17]. Furthermore, acetophenone thiosemicarbazone (APTSC) has been identified by means of the Zscan technique as a NLO material with third-order harmonic generation capability [17].…”

Section: Introductionmentioning

confidence: 99%

“…The extensive electron delocalization in the thiosemicarbazone (TSC) moiety greatly improves the SHG efficiency of free TSC ligands and their metal complexes [17]. Furthermore, acetophenone thiosemicarbazone (APTSC) has been identified by means of the Zscan technique as a NLO material with third-order harmonic generation capability [17]. Because MAPTSC has a powerful electron donor (−OCH 3 ) appended to the benzene ring which is not the case in APTSC.…”

Section: Introductionmentioning

confidence: 99%

Concomitant Effects of Transition Metal Chelation and Solvent Polarity on the First Molecular Hyperpolarizability of 4-Methoxyacetophenone Thiosemicarbazone: A DFT Study

Nkungli

Ghogomu

2016

Journal of Theoretical Chemistry

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Nonlinear optical (NLO) properties of organic and metal-organic materials are of considerable interest to emerging optoelectronic and photonic technologies. Much work has been carried out on the former materials but the latter ones have received less attention till date. Herein, a density functional theory (DFT) study on the combined effects of transition metal chelation and solvent polarity on the first hyperpolarizability ( tot ) of 4-methoxyacetophenone thiosemicarbazone (MAPTSC) is reported. MAPTSC exhibits a tautomeric form with higher optical nonlinearity rendering its NLO response in polar solvents potentially switchable. Our results have revealed significant modifications of the first hyperpolarizability of MAPTSC upon complexation with different transition metal chlorides in the presence of solvents with varying dielectric constants. Therefore, its second-order NLO response is highly tunable by the synergy of transition metal chelation and solvent polarity. MAPTSC and its Zn(II) and Pt(II) chloride complexes are promising NLO materials because their gas-phase tot values are larger than those of the prototype push-pull molecules, paranitroaniline (PNA) and urea, by factors of about 1. 40-1.76 and 19.57-37.24, respectively; these factors greatly increase in polar solvent medium. Moreover, they possess high optical transparencies in the visible region of the electromagnetic spectrum which mitigate transparency/nonlinearity trade-offs, thereby increasing the likelihood of broad band NLO response.

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“…18 . The presence of multiple donor atoms within the same ligand multiplying coordination modes affects the properties of ligands and complexes 19,20 and in the same time thiosemicarbazones exist in equilibrium of various tautomers or conformers which greatly affects their chelating ability 21,22 . On the other hand Nickel can take up different coordination environments (such as octahedral, square-planar and tetrahedral).…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure and DFT Calculation Studies of Ni (II) Cinnamaldehyde Thiosemicarbazone Complex

2015

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Slow evaporation of a dilute DMSO solution of the title compound at room temperature, provided a brown crystal of Ni(CMTSC)2DMSO suitable for X-Rays study (space group: (5)). Two Ni atoms were located on special positions providing two molecules of Ni(CMTSC)2 different for their torsion angles and intermolecular interactions. In both molecules, the thiosemicarbazone coordinates as an anionic ligand via the thiosemicarbazone moiety's azomethine nitrogen and thiolatosulphur in a square-planar geometry. In the aim of investigating structural features, Density Functional Theory calculations of both ligand and complex were fully optimised with respect to the energy using B3LYP level. The predicted geometry parameters are compared with their corresponding X-ray crystallographic data.

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Synthesis and spectral characterization of acetophenone thiosemicarbazone—A nonlinear optical material

Cited by 52 publications

References 17 publications

Biocompatibility, in Vitro Antiproliferative, and in Silico EGFR/VEGFR2 Studies of Heteroleptic Metal(II) Complexes of Thiosemicarbazones and Naproxen

Biocompatibility, in Vitro Antiproliferative, and in Silico EGFR/VEGFR2 Studies of Heteroleptic Metal(II) Complexes of Thiosemicarbazones and Naproxen

Concomitant Effects of Transition Metal Chelation and Solvent Polarity on the First Molecular Hyperpolarizability of 4-Methoxyacetophenone Thiosemicarbazone: A DFT Study

Crystal Structure and DFT Calculation Studies of Ni (II) Cinnamaldehyde Thiosemicarbazone Complex

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