Synthesis and Characterization of Poly(azomethine ester)s with a Pendent Dimethoxy Benzylidene Group

Vasanthi, B. Joy; Ravikumar, L.

doi:10.4236/ojpchem.2013.33013

Cited by 19 publications

(10 citation statements)

References 38 publications

(35 reference statements)

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“…In the case of F2 , the FTIR spectrum showed signals at 3,483 cm −1 (νOH); 3,288 cm −1 (νOH); 3,153 and 3,057 cm −1 (νNH 2 ) and at 2,959 cm −1 , assigned to the stretch modes of –CH groups (Bukowska, 1979 ; Singh, 2008 ; Greve et al, 2012 ) (Figures S4 , S5 in the Supplementary Materials). In both cases, peaks assigned as the azomethine –C = N– frequencies (Giannicchi et al, 2013 ; Vasanthi and Ravikumar, 2013 ; Senol and Kaya, 2017 ), and –C = C– stretching were observed at 1,640 and 1,591 cm −1 for F1 , and at 1,628 and 1,581 cm −1 for F2 , respectively.…”

Section: Resultsmentioning

confidence: 94%

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

et al. 2018

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It has been reported that the structure of the Schiff bases is fundamental for their function in biomedical applications. Pyridine Schiff bases are characterized by the presence of a pyridine and a phenolic ring, connected by an azomethine group. In this case, the nitrogen present in the pyridine is responsible for antifungal effects, where the phenolic ring may be also participating in this bioactivity. In this study, we synthesized two new pyridine Schiff Bases: (E)-2-[(3-Amino-pyridin-4-ylimino)-methyl]-4,6-difluoro-phenol (F1) and (E)- 2-[(3-Amino-pyridin-4-ylimino)-methyl]-6-fluoro-phenol (F2), which only differ in the fluorine substitutions in the phenolic ring. We fully characterized both F1 and F2 by FTIR, UV-vis, 1H; 13C; 19F-NMR, DEPT, HHCOSY, TOCSY, and cyclic voltammetry, as well as by computational studies (DFT), and NBO analysis. In addition, we assessed the antifungal activity of both F1 (two fluorine substitution at positions 4 and 6 in the phenolic ring) and F2 (one fluorine substitution at position 6 in the phenolic ring) against yeasts. We found that only F1 exerted a clear antifungal activity, showing that, for these kind of Schiff bases, the phenolic ring substitutions can modulate biological properties. In addition, we included F1 and F2 into in epichlorohydrin-β-cyclodextrin polymer (βCD), where the Schiff bases remained inside the βCD as determined by the ki, TGA, DSC, and SBET. We found that the inclusion in βCD improved the solubility in aqueous media and the antifungal activity of both F1 and F2, revealing antimicrobial effects normally hidden by the presence of common solvents (e.g., DMSO) with some cellular inhibitory activity. The study of structural prerequisites for antimicrobial activity, and the inclusion in polymers to improve solubility, is important for the design of new drugs.

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Section: Resultsmentioning

confidence: 94%

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

et al. 2018

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“…They are of the interest due to their unique performance properties namely, high mechanical strength, high-thermal stability, environmental resistance, and are promising materials in photonic and opto-electronic applications (Vasanthi and Ravikumar 2013).…”

Section: Liquid Crystal Poly(azomethine Esters)mentioning

confidence: 99%

New Liquid Crystalline Poly(azomethine esters) Derived from PET Waste Bottles

Issam¹,

Khizrien²

2015

Liquid Crystalline Polymers

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“…C–H sp 3 stretching (hexyl aliphatic side) occurred at 2934 cm −1 for MNP@P3TArH. Schiff base peaks (C=N) were observed at 1674 and 1685 cm −1 for MNP@P3TArH [ 59 ]. C=C aromatic symmetric and asymmetric absorption bands demonstrated in the range of 1573–1461 cm −1 occurred for both nanocomposites.…”

Section: Resultsmentioning

confidence: 99%

Novel Functionalized Polythiophene-Coated Fe3O4 Nanoparticles for Magnetic Solid-Phase Extraction of Phthalates

2016

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Poly(phenyl-(4-(6-thiophen-3-yl-hexyloxy)-benzylidene)-amine) (P3TArH) was successfully synthesized and coated on the surface of Fe 3 O 4 magnetic nanoparticles (MNPs). The nanocomposites were characterized by Fourier transform infra-red (FTIR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller (BET) surface area analysis, analyzer transmission electron microscopy (TEM) and vibrating sample magnetometry (VSM). P3TArH-coated MNPs (MNP@P3TArH) showed higher capabilities for the extraction of commonly-used phthalates and were optimized for the magnetic-solid phase extraction (MSPE) of environmental samples. Separation and determination of the extracted phthalates, namely dimethyl phthalate (DMP), diethyl phthalate (DEP), dipropyl phthalate (DPP), dibutyl phthalate (DBP), butyl benzyl phthalate (BBP), dicyclohexyl phthalate (DCP), di-ethylhexyl phthalate (DEHP) and di-n-octyl phthalate (DNOP), were conducted by a gas chromatography-flame ionization detector (GC-FID). The best working conditions were as follows; sample at pH 7, 30 min extraction time, ethyl acetate as the elution solvent, 500-µL elution solvent volumes, 10 min desorption time, 10-mg adsorbent dosage, 20-mL sample loading volume and 15 g¨L´1 concentration of NaCl. Under the optimized conditions, the analytical performances were determined with a linear range of 0.1-50 µg¨L´1 and a limit of detection at 0.08-0.468 µg¨L´1 for all of the analytes studied. The intra-day (n = 7) and inter-day (n = 3) relative standard deviations (RSD%) of three replicates were each demonstrated in the range of 3.7-4.9 and 3.0-5.0, respectively. The steadiness and reusability studies suggested that the MNP@P3TArH could be used up to five cycles. The proposed method was executed for the analysis of real water samples, namely commercial bottled mineral water and bottled fresh milk, whereby recoveries in the range of 68%-101% and RSD% lower than 7.7 were attained.

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Synthesis and Characterization of Poly(azomethine ester)s with a Pendent Dimethoxy Benzylidene Group

Cited by 19 publications

References 38 publications

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

New Liquid Crystalline Poly(azomethine esters) Derived from PET Waste Bottles

Novel Functionalized Polythiophene-Coated Fe3O4 Nanoparticles for Magnetic Solid-Phase Extraction of Phthalates

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