Study of new ferrocene-based thioureas as potential nonionic surfactants

Fatima, Saira; Badshah, Amin; Lal, Bhajan; Asghar, Faiza; Tahir, Muhammad Nawaz; Shah, Afzal; Ullah, Imdad

doi:10.1016/j.jorganchem.2016.07.003

Cited by 24 publications

(11 citation statements)

References 45 publications

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“…Calculations predict the polar head group and its lipophilic tail are directed to opposite sides in a straight orientation. The straight orientation of the alkyl chain is not astonishing in the case of surfactants, as it was also observed in a number of previous studies (Cheng et al, ; Fatima et al, ; Xu et al, ). As is known, surfactant molecules assemble into micelles due to their aversion to nonpolar lipophilic interactions with the polar solvent.…”

Section: Resultssupporting

confidence: 60%

“…FCA16 shows stretching vibration bands of sp 3 –C–H below 3000 cm −1 , sp 2 C–H stretching at 3091 cm −1 , –N=CH– stretching at 1640–1644 cm −1 , –CH 2 bending at 1466 cm −1 , C=C stretching of ferrocene at 1104 cm −1 , H‐C = bending at 818 cm −1 (Shaban et al, ), CH 3 bending at 1370–1375 cm −1 , and Fe‐Cp stretch at 484 cm −1 (Fatima et al, ). All the synthesized surfactants show the same characteristic peaks at the same positions.…”

Section: Resultsmentioning

confidence: 99%

“…The CMC of the synthesized surfactants was determined using UV–visible spectroscopy according to the method reported in the literature (Fatima et al, ). Different concentrations of the synthesized surfactants were prepared in the range of 0.0005–2 mM using ethanol as a solvent.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Characterization, and Computational Study of New Ferrocene‐Based Schiff Bases as Potential Nonionic Surfactants

Ali

Badshah

Hussain

et al. 2019

J Surfact & Detergents

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Ferrocene‐based nonionic surfactants were synthesized by reacting ferrocenylcarboxyaldehyde with different long‐chain amines. Nonionic surfactants were characterized using Fourier transform infrared spectra (FT‐IR), 1HNMR, and 13CNMR spectroscopy. The ferrocene‐based surfactants were characterized using ultraviolet (UV)–visible spectroscopy and surface tension measurements to determine the critical micelle concentration (CMC). The CMC values indicate high aggregation ability of the synthesized surfactants in ethanol. Dominance of their hydrophilic character was ensured from hydrophilic–lipophilic balance in the 10–15 range. Voltammetric response of all surfactants showed well‐defined and stable redox signals. Computational studies further revealed their physicochemical characteristics. Results of the study confirm the multifunctionality of the surfactants and suggest utilization in various fields.

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Section: Resultssupporting

confidence: 60%

Section: Resultsmentioning

confidence: 99%

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Synthesis, Characterization, and Computational Study of New Ferrocene‐Based Schiff Bases as Potential Nonionic Surfactants

Ali

Badshah

Hussain

et al. 2019

J Surfact & Detergents

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“…Critical micelle concentration (CMC) of the amphiphiles was determined by using UV-Vis spectroscopy without probe (Fatima et al, 2016). UV-Vis spectra of 2 -EB in water were recorded at varying concentrations (0.001–0.1 mM) and a graph was plotted between absorbance vs. concentration (Figure S1).…”

Section: Resultsmentioning

confidence: 99%

Tunable Self-Assembled Nanostructures of Electroactive PEGylated Tetra(Aniline) Based ABA Triblock Structures in Aqueous Medium

2019

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PEGylated tetra(aniline) ABA triblock structure PEG-TANI-PEG ( 2 ) consisting of tetra(aniline) (TANI) and polyethylene glycol (PEG) was synthesized by coupling the tosylated-PEG to boc-protected NH 2 /NH 2 TANI ( 1 ) through a simple nucleophilic substitution reaction. Deprotection of 2 resulted in a leucoemeraldine base state of TANI ( 2 -LEB), which was oxidized to stable emeraldine base ( 2 -EB) state. 2 -EB was doped with 1 M HCl to emeraldine salt ( 2 -ES) state. FTIR, 1 H and 13 C NMR and UV-Vis-NIR spectroscopy, and MS (ESI) was used for structural characterization. The synthesized triblock structure exhibited good electroactivity as confirmed by CV and UV-Vis-NIR spectroscopy. Self-assembling of the triblock structure in aqueous medium was assessed by DLS, TEM, and SEM. Spherical aggregates were observed with variable sizes depicting the effect of concentration and oxidation of 2 -LEB. Further, the aggregates showed acid/base sensitivity as evaluated by doping and dedoping of 2 -EB with 1 M HCl and 1 M NH 4 OH, respectively. Future applications in drug delivery and sensors are envisaged for such tunable self-assembled nanostructures in aqueous media.

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“…Ferrocene has a redox center, a π‐conjugated system, and an exclusive electron transferability, which makes it a potential candidate to be used as an electronic mediator in electrochemical and biosensor devices . Moreover, its stability, hydrophobicity, nontoxicity, and synthetic convenience have attracted researcher's interest to employ it as a redox‐active group in surfactant systems . Functionalized ferrocenes play diverse roles in modern chemistry, with systems featuring pendant Lewis basic groups acting as donor ligands in various complexes exploited in homogenous catalysis, and those bearing Lewis acidic groups finding applications, for example, in polymer synthesis and in detection/sensing …”

Section: Introductionmentioning

confidence: 99%

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

Mahmoud

2019

J Chinese Chemical Soc

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A novel bidentate Schiff base ligand (HL, Nanobidentate Ferrocene based Schiff base ligand L (has one replaceable proton H)) was prepared via the condensation of 2‐amino phenol with 2‐acetyl ferrocene. The ligand was characterized using elemental analysis, mass spectrometry, infrared (IR) spectroscopy, 1proton nuclear magnetic resonance (H‐NMR) spectroscopy, scanning electron microscopy (SEM), and thermal analysis. The corresponding 1:1 metal complexes with some transition‐metal ions were additionally characterized by their elemental analysis, molar conductance, SEM, and thermogravimetric ana1ysis (TGA). The complexes had the general formula [M(L)(Cl)(H2O)3]xCl·nH2O (M = Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II)), (x = 0 for Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II), x = 1 for Cr(III) and Fe(III)), (n = 1 for Cr(III), n = 3 for Mn(II) and Co(II), n = 4 for Fe(III), Ni(II), Cu(II), Zn(II), and Cd(II)). Density functional theory calculations on the HL ligand were also carried out in order to clarify molecular structures by the B31YP exchange‐correlation function. The results were subjected to molecular orbital diagram, highest occupied mo1ecu1ar orbital–lowest occupied molecular orbital, and molecular electrostatic potential calculations. The parent Schiff base and its eight metal complexes were assayed against four bacterial species (two Gram‐negative and two‐Gram positive) and four different antifungal species. The HL ligand was docked using molecular operating environment 2008 with crystal structures of oxidoreductase (1CX2), protein phosphatase of the fungus Candida albicans (5JPE), Gram(−) bacteria Escherichia coli (3T88), Gram(+) bacteria Staphylococcus aureus (3Q8U), and an androgen‐independent receptor of prostate cancer (1GS4). In order to assess cytotoxic nature of the prepared HL ligand and its complexes, the compounds were screened against the Michigan cancer foundation (MCF)‐7 breast cancer cell line, and the IC50 values of compounds were calculated.

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Study of new ferrocene-based thioureas as potential nonionic surfactants

Cited by 24 publications

References 45 publications

Synthesis, Characterization, and Computational Study of New Ferrocene‐Based Schiff Bases as Potential Nonionic Surfactants

Synthesis, Characterization, and Computational Study of New Ferrocene‐Based Schiff Bases as Potential Nonionic Surfactants

Tunable Self-Assembled Nanostructures of Electroactive PEGylated Tetra(Aniline) Based ABA Triblock Structures in Aqueous Medium

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

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