Synthesis, spectroscopic characterization, biological screening, and theoretical studies of organotin(IV) complexes of semicarbazone and thiosemicarbazones derived from (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone

Singh, Har Lal; Singh, Jangbhadur; Bhanuka, Sunita

doi:10.1007/s11164-015-2069-3

Cited by 29 publications

(14 citation statements)

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“…The UV-vis spectra of the organotin (IV) complexes in Figure S1 ( Supplementary Materials ) were recorded in methanol solution (1 × 10 −3 M). Observed bands in the region of 268 nm to 270 nm were assigned to the π-π* transitions, meanwhile, the bands at 322–336 nm and 433–379 nm to the π-π* and n-π* transitions, both associated with the azomethine group [ 51 ]. The spectral analysis showed a red shift in the absorption wavelength, due to the electron withdrawing effect of substituent on the aromatic ring.…”

Section: Resultsmentioning

confidence: 99%

Design of Promising Heptacoordinated Organotin (IV) Complexes-PEDOT: PSS-Based Composite for New-Generation Optoelectronic Devices Applications

et al. 2021

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The synthesis of four mononuclear heptacoordinated organotin (IV) complexes of mixed ligands derived from tridentated Schiff bases and pyrazinecarboxylic acid is reported. This organotin (IV) complexes were prepared by using a multicomponent reaction, the reaction proceeds in moderate to good yields (64% to 82%). The complexes were characterized by UV-vis spectroscopy, IR spectroscopy, mass spectrometry, 1H, 13C, and 119Sn nuclear magnetic resonance (NMR) and elemental analysis. The spectroscopic analysis revealed that the tin atom is seven-coordinate in solution and that the carboxyl group acts as monodentate ligand. To determine the effect of the substituent on the optoelectronic properties of the organotin (IV) complexes, thin films were deposited, and the optical bandgap was obtained. A bandgap between 1.88 and 1.98 eV for the pellets and between 1.23 and 1.40 eV for the thin films was obtained. Later, different types of optoelectronic devices with architecture “contacts up / base down” were manufactured and analyzed to compare their electrical behavior. The design was intended to generate a composite based on the synthetized heptacoordinated organotin (IV) complexes embedded on the poly(3,4-ethylenedyoxithiophene)-poly(styrene sulfonate) (PEDOT:PSS). A Schottky curve at low voltages (<1.5 mV) and a current density variation of as much as ~ 3×10−5 A/cm2 at ~ 1.1 mV was observed. A generated photocurrent was of approximately 10−7 A and a photoconductivity between 4×10−9 and 7×10−9 S/cm for all the manufactured structures. The structural modifications on organotin (IV) complexes were focused on the electronic nature of the substituents and their ability to contribute to the electronic delocalization via the π system. The presence of the methyl group, a modest electron donor, or the non-substitution on the aromatic ring, has a reduced effect on the electronic properties of the molecule. However, a strong effect in the electronic properties of the material can be inferred from the presence of electron-withdrawing substituents like chlorine, able to reduce the gap energies.

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Section: Resultsmentioning

confidence: 99%

Design of Promising Heptacoordinated Organotin (IV) Complexes-PEDOT: PSS-Based Composite for New-Generation Optoelectronic Devices Applications

et al. 2021

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“…These compounds exhibited excellent inhibitory effect on the bacterial growth. Compounds 14, 17 and 18 showed most inhibitory effect against gram negative bacteria E. coli and compounds 14 and 18 showed highest activity against K. pneumoniae . The results suggested that gram positive bacteria were found to be more susceptible as compared to the Gram negative bacteria, which may be due to the fact that the cell wall of Gram negative bacteria has more antigenic properties due to the presence of an outer lipid membrane of lipopolysaccharides . In antifungal activity, compounds 10, 13, 14, 17 and 18 were found to be more active against A. niger and compounds 14, 17 and 18 against C. albicans . Antimicrobial data exhibited that all the silicon and tin complexes were better inhibitor of bacterial and fungal growth as compared to their Schiff base ligands and exhibited lower MICs against all the microbial strains.…”

Section: Resultsmentioning

confidence: 97%

“…The results suggested that gram positive bacteria were found to be more susceptible as compared to the Gram negative bacteria, which may be due to the fact that the cell wall of Gram negative bacteria has more antigenic properties due to the presence of an outer lipid membrane of lipopolysaccharides . In antifungal activity, compounds 10, 13, 14, 17 and 18 were found to be more active against A. niger and compounds 14, 17 and 18 against C. albicans .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Activity and QSAR Studies of Organotin(IV) and Organosilicon(IV) Complexes

Devi

Yadav

et al. 2019

ChemistrySelect

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A panel of penta‐coordinated, neutral organotin(IV) and organosilicon(IV) complexes of newly designed Schiff bases: 4‐(2‐hydroxymethyl‐phenylimino)‐2‐methyl‐4H‐pyran‐3‐ol (H2L1) and 4‐(benzothiazol‐2‐ylimino)‐2‐methyl‐4H‐pyran‐3‐ol (HL2) were synthesized and characterized using elemental analysis, spectral studies (UV/Vis, IR, 1H, 13C, 29Si, 119Sn NMR and Fluorescence) and thermal technique. Spectral studies conferred that the Schiff base act as bi/tridentate and form the penta coordinated geometry with oxygen and nitrogen donor atom (NO/NOO). The compounds were screened for in vitro antimicrobial activity using twofold serial dilution method against Gram‐positive bacteria (Staphylococcus aureus, Bacillus cereus), Gram‐negative bacteria (Escherichia coli, Klebsiella pneumoniae) and fungi (Aspergillus niger, Candida albicans). The antimicrobial study exposed good activity with tri‐ and di‐phenyl derivatives exhibiting excellent biological activity. Compounds 5, 6, 10, 13, 14, 17 and 18 displayed better activity than the standard drugs. Quantitative structure activity relationship involves correlation of biological activity with the structural properties of the compounds using statistical means.

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“…Thiosemicarbazones are an important class of compounds that have received wide attention due to their many biological and pharmacological properties, such as anti-bacterial, anti-viral, anti-neoplastic and anti-malarial activities (Kovala-Demerzi et al, 1997;Hu et al, 2006;Khan & Yusuf, 2009). Thiosemicarbazone Schiff bases are similar to their dithiocarbazate counterparts in that complexation with a metal centre is achieved via the nitrogen and sulfur atoms following deprotonation of the S-H and N-H groups (Ðilović et al, 2008;Wiecek et al, 2009;Pavan et al, 2010;Parrilha et al, 2011;Singh et al, 2016;Palanimuthu et al, 2017). Tin(IV) compounds of 3-methoxysalicylaldehyde thiosemicarbazone have been evaluated for their in vitro cytotoxicity against a line of human T lymphocyte cells, Jurkat cells (Khandani et al, 2013): in this study, a structure-activity analysis for the dialkyltin(IV) compounds indicated that cytotoxicity increased with the length of the alkyl carbon chain of the tin-bound substituents.…”

Section: Chemical Contextmentioning

confidence: 99%

Di-n-butyl[N′-(3-methoxy-2-oxidobenzylidene)-N-phenylcarbamohydrazonothioato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

Yusof¹,

Kwong²,

Karunakaran³

et al. 2021

Acta Cryst E

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The title diorganotin Schiff base derivative, [Sn(C4H9)2(C15H13N3O2S)], features a penta-coordinated tin centre defined by the N,O,S-donor atoms of the di-anionic Schiff base ligand and two methylene-C atoms of the n-butyl substituents. The resultant C2NOS donor set defines a geometry intermediate between trigonal–bipyramidal and square-pyramidal. In the crystal, amine-N—H...O(methoxy) hydrogen bonding is found in a helical, supramolecular chain propagating along the b-axis direction. The chains are assembled into a layer parallel to (\overline{1}01) with methylene-C—H...π(phenyl) interactions prominent; layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surface showed the presence of weak methylene-C—H...π(phenyl) interactions and short H...H contacts in the inter-layer region. Consistent with the nature of the identified contacts, the stabilization of the crystal is dominated by the dispersion energy term.

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Synthesis, spectroscopic characterization, biological screening, and theoretical studies of organotin(IV) complexes of semicarbazone and thiosemicarbazones derived from (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone

Cited by 29 publications

References 50 publications

Design of Promising Heptacoordinated Organotin (IV) Complexes-PEDOT: PSS-Based Composite for New-Generation Optoelectronic Devices Applications

Design of Promising Heptacoordinated Organotin (IV) Complexes-PEDOT: PSS-Based Composite for New-Generation Optoelectronic Devices Applications

Synthesis, Biological Activity and QSAR Studies of Organotin(IV) and Organosilicon(IV) Complexes

Di-n-butyl[N′-(3-methoxy-2-oxidobenzylidene)-N-phenylcarbamohydrazonothioato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

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