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Effect of Au and Au@ag Core-Shell Nanoparticles on the SERS of Bridging Organic Molecules
(ACADEMIC PRESS INC ELSEVIER SCIENCE, 2010) Güzel, Remziye; Üstündağ, Zafer; Ekşi, Haslet; Keskin, Selda; Taner, Bilge; Durgun, Zeynep Gülşah; Turan, Aybüke A. İşbir; Solak, Ali Osman
Gold nanoparticles (AuNPs) with about 6 nm size were produced and stabilized with mercaptopropionic acid (MPA) film to produce a monolayer protected cluster (MPC) of AuS(CH2)(2)COOH. 4-Aminothiophenol (ATP) molecules were introduced to the activated carboxylic acid ends of the film surrounding the AuNPs to produce AuS(CH2)(2)CONHPhSH MPC. These modified AuNPs were again self-assembled with Au@Ag core-shell bimetallic nanoparticles via the -SH groups to produce an organic bridge between Au and Au@Ag metallic nanoparticles. An unusually strong enhancement of the Raman signals was observed and assigned to the plasmon coupling between the AuNPs and Au@Ag NPs bridged assembly. Formation of AuS(CH2)(2)COOH and AuS(CH2)(2)CONHPhSH clusters and AuS(CH2)(2)CONHPhS(Au@Ag) assembly is confirmed by UV-Vis, reflection-absorption IR spectroscopy (RAIRS) and X-ray photoelectron spectroscopy (XPS), as well as by TEM analysis. The SERS activity of the AuNPs and Au@Ag NPs was tested using the HS(CH2)(2)CONHPhSH molecule as a probe to compare the effectiveness of monometallic and bimetallic systems. SERS spectra show that Au@Ag bimetallic nanoparticles are very effective SERS-active substrates.
The example of calix[4]pyrrole derivative containing Bodipy unit: Fluorometric and colorimetric sensor for F- ion
(PERGAMON-ELSEVIER SCIENCE LTD, 2014) Taner, Bilge; Kursunlu, Ahmed Nuri; Guler, Ersin
A novel chemosensor based on calix[4]pyrrole derivative modified by Bodipy unit has been synthesized, and its complexes with various anions were investigated. The results show that the receptors can selectively recognize biologically important fluoride ions. The binding affinity for fluoride ions was investigated by naked-eye color change, absorption, emission, proton nuclear magnetic resonance spectroscopy. The addition of fluoride ions to an acetonitrile solution of chemosensor can result in an obvious color change (brownish yellow color to straw yellow). The stoichiometries between the receptor and fluoride were determined from the molar ratio plots using the UV-visible spectra, which showed evident 1:1. The proton nuclear magnetic resonance spectral data supported the fluoride anion recognition with the disappearance of the amino proton peaks. Published by Elsevier B.V.
Fabrication of Calix[4]pyrrole Nanofilms at the Glassy Carbon Surface and Their Characterization by Spectroscopic, Optic and Electrochemical Methods
(Elsevier Science Sa, 2010) Taner, Bilge; Özcan, Emine; Üstündağ, Zafer; Keskin, Selda; Solak, Ali Osman; Ekşi, Haslet
meso-Octamethylcalix[4]pyrrole (CP) and meso-heptaethylcalix[4]pyrrole-meso-4-aminophenyl (4APCP) modified glassy carbon (GC) electrodes were prepared by the electrochemical oxidation in acetonitrile solution. Binding of the calix[4]pyrroles with the glassy carbon surface was investigated that it is through the etheric linkage revealed from the reflection absorption infrared spectroscopy (RAIRS). Surface films of CP and 4APCP were investigated by cyclic voltammetry (CV), ellipsometry, X-ray photoelectron spectroscopy. RAIRS and the contact angle measurements. The thicknesses of the films were determined by ellipsometry which confirmed that the film was multilayer and homogeneous over the surface. Ellipsometric measurements also provided that the CP and 4APCP film thicknesses were 2.49 nm and 4.58 nm for 6 CV cycle modification, corresponding to 66 mu F/cm(2) and 106 mu F/cm(2) capacitances obtained by CV. The wetting behavior was examined by contact angle measurements and found that the hydrophobicity of the GC-4APCP surface was higher than that of GC-CP, probably due to the aromatic meso substituent present in the former.
The first example of calix[4]pyrrole functionalized vic-dioxime ligand: Synthesis, characterization, spectroscopic studies and redox properties of the mononuclear transition metal complexes
(ELSEVIER SCIENCE SA, 2010) Taner, Bilge; Deveci, Pervin; Bereket, Soner; Solak, Ali Osman; Ozcan, Emine
Novel calix[4] pyrrole bearing vic-dioxime ligand (LH2) of the general formula, R1R2C2N2O2H2 (where, R-1 = C6H5- and R-2 = C39H50N5-) has been synthesized by the reaction of anti-chlorophenylglyoxime with 3-aminophenylcalix[4] pyrrole at room temperature. The mononuclear Cu(II), Ni(II) and Co(II) complexes of this vic-dioxime ligand were prepared and their structures were confirmed by elemental analysis, FT-IR, TGA and magnetic susceptibility measurements; the HMBC, DEPT, H-1 and C-13 NMR spectra of the LH2 ligand were also reported. The electrochemical property of the complexes was investigated in DMSO by cyclic voltammetry at 200 mV s (1) scan rate. The cyclic voltammetric measurements clearly indicated that Co(LH)(2)center dot 2H(2)O complex differs from the Ni(LH)(2) and Cu(LH)(2) complexes upon the exhibition of quasi-reversible one-electron transfer reduction process in the negative region instead of an irreversible process. (C) 2010 Elsevier B. V. All rights reserved.
Kaliks[4]pirol taşıyan vic-dioksim ligandlarının ve geçiş metal komplekslerinin sentezi; elektrokimyasal ve spektrokimyasal özelliklerinin incelenmesi
(Selçuk Üniversitesi Fen Bilimleri Enstitüsü, 2011-02-18) Taner, Bilge; Özcan, Emine
Bu çalışmada, amino grubu taşıyan kaliks[4]pirol bileşiği ile glioksim molekülünün bir arada bulunduğu vic-dioksim ligandları (13,14) sentezlenmiştir. Sentezlenen vic-dioksim ligandının Ni(II), Cu(II), Co(II), Zn(II) ve Cd(II) geçiş metalleri ile kompleks bileşikleri sentezlenmiş ve yapıları elementel analiz, FTIR, 1H- NMR teknikleri kullanılarak aydınlatılmıştır. Bu komplekslerin dönüşümlü voltametri (CV) tekniği kullanılarak DMSO çözeltisinde 200 mVs?1 tarama hızında elektrokimyasal özellikleri incelenmiştir. Oktametilkaliks[4]pirol, 3-aminofenil kaliks[4]pirol ve 4-aminofenilkaliks[4]pirol bileşiklerinin asetonitril çözeltisinde, elektrokimyasal oksidasyon metodu ile modifiye edilmiş camsı karbon elektrot yüzeyleri hazırlanmıştır. Hazırlanan bütün yüzeyler, CV tekniğiyle çeşitli redoks problar (dopamine ve ferrisiyanür) kullanılarak karakterize edilmiştir. Yansıtmalı absorpsiyon infrared spektroskopisi (RAIRS) kullanılarak, kaliks[4]pirol türevlerinin camsı karbon elektrot yüzeyine eterik bağlarla bağlandığı bulunmuştur. Hazırlanan bütün yüzeyler, çeşitli spektroskopik ve mikroskobik tekniklerle (X-ışını fotoelektron spektroskopisi, Raman spektroskopisi, temas açısı ölçümü tekniği, elipsometri ve atomik kuvvet mikroskobisi) karakterize edilmiştir.
Mesoporous silica and chitosan based pH-sensitive smart nanoparticles for tumor targeted drug delivery
(SPRINGER, 2017) Deveci, Pervin; Taner, Bilge; Albayati, Safaa Hashim Mohammed
Although various therapies have been developed for cancer treatment, chemotherapy plays a vital role, but still faces many challenges, such as severe cytotoxicity, side effects, multidrug resistance, and poor tumor selectivity. The development of targeted drug delivery has provided new strategies for addressing the limitations of the conventional chemotherapy, and has become more significant in clinical research in recent times. Among the various stimuli, pH triggered delivery is regarded as the most general strategy, targeting the acidic extracellular microenvironment and intracellular organelles of solid tumors. It is well-known that the extracellular pH of most tumor tissues is more acidic (pH 6.5-6.8) than that of normal tissues (pH 7.4). In our present review, we focus on some of the recent literature reports on the fabrication and application of pH-sensitive smart nanoparticles for tumor targeted drug delivery system. The strategies to the chemical design of these nanocarriers and their clinical findings are discussed. Particular focus is given to silica, chitosan, and silica-chitosan based nanocarriers. These smart nanoparticles will have a promising platform in improving human health and quality of life.
Modification of glassy carbon electrode by the electrochemical oxidation of 3-aminophenylcalix[4]pyrrole in nonaqueous media
(Wiley, 2012) Taner, Bilge; Deveci, Pervin; Üstündağ, Zafer; Keskin, Selda; Özcan, Emine; Solak, Ali Osman
3-Aminophenylcalix[4]pyrrole (3APCP) was grafted to a glassy carbon (GC) surface during the electrochemical oxidation process in 0.1 M tetrabutylammoniumtetra-fluoroborate (TBATFB) containing acetonitrile solution. The presence of a surface film was confirmed electrochemically by comparing voltammograms of dopamine and ferricyanide redox probes at the bare and modified electrodes. Reflection-absorption infrared spectroscopy (RAIRS), XPS, atomic force microscopy (AFM), ellipsometry and the contact angle measurements were also employed to characterize 3APCP film on GC electrode. RAIRS analysis revealed that calix[4]pyrrole was bonded to the glassy carbon surface via the etheric linkage. The stability of the modified GC electrode was also studied. Copyright (C) 2011 John Wiley & Sons, Ltd.
New supramolecular compounds: the complexes of nickel(II), copper(II), cobalt(II), cadmium(II) and zinc(II) with anti- [N-(4-aminophenyl)aza-15-crown-5]-4-(phenoxy)phenylglyoxime ligand
(SPRINGER, 2015) Ozpinar, Kursat; Deveci, Pervin; Kilinc, Merve; Ozcan, Emine; Karaman, Burcu Dilyuz; Karaarslan, Havva; Taner, Bilge
A new vic-dioxime ligand (1), bearing pendant an azacrown ether moiety and its soluble mononuclear cadmium(II), zinc(II), nickel(II), copper(II) and cobalt(II) complexes were obtained with the metal: ligand ratios of 1: 2 and 1:1. The structures of the ligand and its complexes were verified using Fourier transform infrared (FT-IR), ultraviolet-visible (UV-Vis), mass spectrometry (MS), H-1 and C-13 NMR techniques. More detailed information about the structure of the 1 was provided by the two-dimensional (2D) heteronuclear single quantum coherence and heteronuclear multiple bond correlation techniques. The complexation properties of the ligand 1 were studied in the presence of different cations such as Pb2+, Zn2+, Cu2+, Cr3+, Hg2+, Zn2+, Fe3+ and Al3+ by UV-Vis spectroscopy and H-1 NMR titration methods. All experimental results indicated that the new ligand acts as a selective compound only for Hg+2 cation. The redox behaviour of the complexes, were investigated by cyclic voltammetry at the glassy carbon electrode in 0.1 M tetrabutylamoniumtetrafluoroborate in dimethyl sulfoxide.
Novel Bioactive Vic-Dioxime Ligand Containing Piperazine Moiety: Synthesis, X-ray Crystallographic Studies, 2D NMR Applications and Complexation With Ni(II)
(Pergamon-Elsevier Science Ltd, 2010) Yılmaz, Aytek; Taner, Bilge; Deveci, Pervin; Yılmaz Obalı, Aslıhan; Arslan, Uğur; Şahin, Ertan; Uçan, H. İsmet; Özcan, Emine
A new vic-dioxime ligand bearing an important pharmacophore substituent, anti-1-(4-benzylpiperazine-1-yl) phenylglyoxime (LH2) (Scheme 1), has been synthesized and its nickel(II) complex was obtained by the reaction of NiCl2 center dot 6H(2)O and the ligand. The characterization of the newly formed compounds was performed by elemental analysis, FT-IR, 1D NMR (H-1, C-13, DEPT), 2D NMR (HMBC), ESI mass-spectrometry, TG/DTA, X-ray crystallography. The antibacterial activity was also studied against Staphylococcus aureus ATCC 25923, Streptococcus mutans RSHM 676, Enterococcus faecalis ATCC 29212, Lactobacillus acidophilus RSHM 06029, Escherichia coli ATCC 25922, E. coli ATCC 35218, Pseudomonas aeruginosa ATCC 27853. The antimicrobial test results indicated that all the compounds have mild antibacterial activity against both Gram negative and Gram positive bacterial species.
A novel vic-dioxime ligand and its Ni(II), Cu(II) and Co(II) complexes containing calix[4]pyrrole moiety: synthesis, characterization and redox properties
(SPRINGER, 2012) Taner, Bilge; Deveci, Pervin; Ozcan, Emine; Solak, Ali Osman
A new calix[4]pyrrole functionalized vic-dioxime, 3-(4-methyl-9,9,14,14,19,19-hexaethylcalix[4]pyrrole)benzoaminoglyoxime (LH2) was synthesized from anti-chloroglyoxime and 3-aminophenyl-calix[4]pyrrole at room temperature. The mononuclear complexes {nickel(II), copper(II) and cobalt(II)} of this vic-dioxime ligand were prepared and their structures were confirmed by elemental analysis, IR and UV-Vis spectrophotometry, magnetic susceptibility; the MS, H-1 and C-13 NMR spectra of the LH2 ligand and its Ni(II) complex were also recorded. The experimental results indicated that the ligand:metal ratio was 2:1 in the cases of Ni(II), Cu(II) and Co(II) complexes as is with most vic-dioximes. Electrochemical properties of the ligand, and its complexes were investigated in DMSO solution by cyclic voltammetry at 200 mV s(-1) scan rate.
Novel vic-dioxime ligand containing calix[4]pyrrole moiety: synthesis, characterization, anion binding studies and complexation with Ni(II)
(SPRINGER, 2014) Taner, Bilge
A new vic-dioxime functionalized calix[4] pyrrole was synthesized from anti-chloroglyoxime and 4-aminophenyl-calix[4] pyrrole at room temperature. The Ni(II) complex has been prepared by reacting the ligand with NiCl2 center dot 6H(2)O in ethanol. These receptors were characterized by elemental analyses, H-1 and C-13 NMR spectra, IR and mass spectra. Electrochemical properties of the ligand, and its Ni(II) complex were investigated in CH2Cl2 solution by cyclic voltammetry at 100 mV s(-1) scan rate. Anion-binding studies were carried out using UV-Vis, and 1 H NMR titrations, revealed that the Ni(II) complex exhibits selective recognition toward F- over other anions. The selectivity for F- among the halides is attributed mainly to the hydrogen-bond interaction of the receptor with F-. Receptor showed colour change from red to brown in the presence of tetrabutylammonium fluoride (TBAF) with 1:2 stoichiometry.
Preparation and Spectral and Biological Investigation of vic-Dioxime Ligands Containing Piperazine Moiety and Their Mononuclear Transition-Metal Complexes
(TAYLOR & FRANCIS INC, 2013) Taner, Bilge; Arslan, Ugur
Two vic-dioxime ligands, N-(4-benzylpiperazine-1-yl) p-tolylglyoxime ((LH2)-H-1) and N,N-bis(4-benzylpiperazine-1-yl) glyoxime ((LH2)-H-2), containing piperazine moieties were synthesized, and their Ni(II), Cu(II), Co(II) and Zn(II) complexes were obtained. The ligands were characterized by elemental analysis, Fourier transform-infrared (FT-IR), ultraviolet-visible NMR (H-1, C-13, and heteronuclear multiple-bond correlation), and electrospray ionization (ESI) mass spectrometry. The isolated complexes were characterized by a combination of elemental analysis, IR, UV-vis, and ESI mass spectrometry and in the case of Ni(II) and Zn(II) complexes by H-1 and C-13 NMR spectroscopy. The electrochemical behaviors of the ligands and their complexes were studied by cyclic voltammetry (CV) in dimethylsulfoxide solution containing tetrabutylammoniumtetrafluoroborate (TBATFB). The antibacterial activity was also studied against S. aureus ATCC 25923, S. aureus ATCC 29213, S. mutans RSHM 676, E. faecalis ATCC 29212, E. coli ATCC 25922, and P. aeruginosa ATCC 27853. The antimicrobial test results indicated that all the compounds have good antibacterial activity against P. auriginosa ATCC 27853 bacteria and were as effective as ampicilin. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resources: Full experimental and spectral details.]
Synthesis and complexation of two new phenylaminoglyoxime ligands
(TAYLOR & FRANCIS LTD, 2008) Deveci, Pervin; Ozcan, Emine; Taner, Bilge; Arslan, Oemer
Two new soluble phenylaminoglyoxime ligands, 4-isopropylanilinephenylglyoxime ((LH2)-H-1), 4-benzylpiperidinephenylglyoxime ((LH2)-H-2), were prepared by reacting 4-isopropylaniline and 4-benzylpiperidine with chlorophenylglyoxime. Mononuclear nickel(II), cobalt(II), copper(II), zinc(II), and cadmium(II) complexes with these ligands were synthesized. On the basis of the magnetic and spectral evidence a square-planar geometry for Ni(II) and Cu(II) complexes, a tedrahedral geometry for Cd(II) and Zn(II) complexes and octahedral geometry for Co(II) complexes are proposed. These compounds were elucidated by elemental analysis, IR, UV-Vis, and magnetic moments. The ligands were additionally characterized by H-1 NMR and C-13 NMR spectra.
Synthesis and electrochemical properties of calix[4]arene derivatives containing ferrocene units in the cone and 1,3-alternate conformation
(PERGAMON-ELSEVIER SCIENCE LTD, 2012) Erdemir, Serkan; Deveci, Pervin; Taner, Bilge; Kocyigit, Ozcan
Two novel calix[4]arene receptors containing ferrocene units in cone (L-1) and 1,3-alternate (L-2) conformations have been synthesized from 25,27-dihydroxy-26,28-bisl(3-aminopropyl)oxy]calix[4]arene 4 or 25,26,27,28-tetra[(3-aminopropyl)oxy]calix[4]arene 6 and ferrocenecarboxaldehyde via condensation, respectively. Their structures have been characterized by H-1, C-13, APT, COSY NMR, FTIR, HSMR, and UV-vis spectral data. The electrochemical behavior of L-1 and L-2 has been investigated in the presence of F-, Cl-, Br-, H2PO4-, CH3COO- anions. Electrochemical studies show that these receptors electrochemically recognize CH3COO-, H2PO4-, and Cl-, anions. Using an UV-vis study, the selectivity to these anions in DMS0 solution was confirmed. (C) 2011 Elsevier Ltd. All rights reserved.
Synthesis and structural and electrochemical characterization of novel macrocyclic vic-dioxime ligand and its mononuclear transition and nontransition metal complexes
(SCIENTIFIC TECHNICAL RESEARCH COUNCIL TURKEY-TUBITAK, 2012) Deveci, Pervin; Taner, Bilge; Kilic, Zeynel; Solak, Ali Osman; Ozcan, Emine
The reaction of N-(4-aminophenyl)aza-15-crown-5 (1) with anti-chlorophenylglyoxime (2) produces a novel azacrown ether containing vic-dioxime, N-(4-aminophenyl)aza-15-crown-5-phenylglyoxime (LH2). LH2 reacts with Ni(II), Cu(II), Co(II), Cd(II), and Zn(II) ions to yield the mononuclear transition and nontransition metal complexes [M(LH)(2)] (M = Ni and Cu), [M(LH)(2) (H2O)(2)] (M = Co), and [M(LH)(H2O) (Cl)] (M = Cd and Zn). The structural features of LH2 were studied using several techniques including elemental analysis. Fourier transform infrared spectroscopy (FT-IR,), ultraviolet visible (UV-Vis), mass spectrometry (MS), 1-dimensional (1D) H-1-NMR and (CNMR)-C-13, distortionless enhancement by polarization transfer (DEPT) 2-dimensional (2D) heteronuclear single-quantum coherence (HSQC), and heteronuclear multiple-bond correlation (HMBC) techniques. The structures of the complexes were confirmed by elemental analyses and with the use of magnetic susceptibility measurements, MS, UV-Vis, FT-IR, H-1-NMR and C-13-NMR techniques. The redox behaviors of the ligand and its Complexes were verified with cyclic voltammetry (CV) at a. glassy carbon (GC) electrode in 0.1 M tetrabutylammoniumtetrafluoroborate (TBATFB) in dimethyl sulfoxide (DMSO).
Synthesis of a new colorimetric receptor based on calix[4]pyrrole binding oxime for selective recognition of fluoride ions
(TAYLOR & FRANCIS LTD, 2014) Taner, Bilge; Alici, Onder; Deveci, Pervin
A colorimetric anion sensor -meso-heptaethylcalix[4]pyrrole-meso-3-aminophenyl-p-nitrobenzaldoxime was synthesised and characterised by various spectroscopic techniques. Anion-binding studies were carried out using UV-vis, and H-1 NMR titrations, revealing that the receptor exhibits selective recognition towards F- over other anions. The selectivity for F- among the halides is attributed mainly to the hydrogen bond interaction of the receptor with F-. Receptor showed colour change from colourless to yellow in the presence of tetrabutylammonium fluoride with 1:2 stoichiometry. Cyclic voltammetry studies, carried out in CH3CN, provided evidence of an anion-dependent electrochemical response with F- ion. This response was particularly dramatic in the case of receptor after the addition of approximate to 1equiv. of F- ion.
Synthesis of some azacrown derivatives and fabrication of their nanofilms on the glassy carbon surface
(SPRINGER, 2012) Deveci, Pervin; Taner, Bilge; Ustundag, Zafer; Kilic, Zeynel; Solak, Ali Osman; Ozcan, Emine
The modification of N-phenyl-aza-15-crown-5 (PA15C5) and N-(4-aminophenyl)-aza-15-crown-5 (4APA15C5) on glassy carbon (GC) electrode was performed by the electrochemical oxidation of the corresponding azacrown derivatives in anhydrous acetonitrile media. The electrochemical behavior of the resulting modified GC electrode was investigated in the presence of electroactive redox probes and these results, together with the X-ray photoelectron spectroscopy (XPS) and reflection-absorption infrared spectroscopy were used to confirm the attachment of these molecules onto the GC surface. The ellipsometric thicknesses of PA15C5 and 4APA15C5 films at the GC surface was obtained around 9.28 +/- 0.40 and 10.50 +/- 1.10 nm, respectively. Azacrown modified nanoscale surfaces serve as alkali metal sensor specific for their cavity in the crown ring.
Synthesis, Characterization, Thermal and Redox Properties of a Vic-Dioxime and Its Metal Complexes
(TAYLOR & FRANCIS LTD, 2010) Uçar, Asuman; Deveci, Pervin; Taner, Bilge; Fındık, Mükerrem; Bereket, Soner; Özcan, Emine; Solak, Ali Osman
A new vic-dioxime ligand containing benzophenone hydrazone units, N'-(benzophenone hydrazone)glyoxime [LH2] has been prepared from benzophenone hydrazone and anti-chloroglyoxime in absolute ethanol. Mononuclear nickel(II), cobalt(II), copper(II), zinc(II), and cadmium(II) complexes were also synthesized. Ligand and complexes were characterized by elemental analyses, FT-IR, 1H NMR, and 13C NMR spectroscopy, magnetic moments, and DTA/TG techniques. On the basis of the magnetic and spectral evidences a square-planar geometry for Ni(II) and Cu(II) complexes, tetrahedral for Cd(II) and Zn(II) complexes, and octahedral for Co(II) complex were proposed. Redox behaviors of ligand and its complexes were also investigated by cyclic voltammetry at the glassy carbon electrode.
Synthesis, electrochemical and structural characterization of novel azacrown ether containing macrocyclic redox-active vic-dioxime ligand and its mononuclear transition metal complexes: Application of DEPT, HSQC, HMBC-NMR and cyclic voltammetry
(PERGAMON-ELSEVIER SCIENCE LTD, 2011) Deveci, Pervin; Taner, Bilge; Kilic, Zeynel; Solak, Ali Osman; Arslan, Ugur; Ozcan, Emine
This paper presents a new azacrown containing vic-dioxime: anti-N-(4-aminophenyl)aza-15-crown-5-glyoxime (LH2), and its mononuclear nickel(II), copper(II), cobalt(II), cadmium(II) and zinc(II) complexes. The azacrown moieties appended at the periphery of the oxime provide solubility for the vic-dioxime ligand and complexes in common organic solvents. The mononuclear M(LH)(2) (M = Ni and Cu), M(LH)(2)(H2O)(2) (M = Co) and [M(LH)(H2O)(Cl)] (M = Cd and Zn) complexes have been obtained with the metal:ligand ratios of 1:2 and 1:1. The structure of the ligand is confirmed by elemental analysis, Fourier transform infrared (FT-IR), ultraviolet-visible (UV-Vis), mass spectrometry (MS), one-dimensional (1D) H-1, C-13 NMR, distortionless enhancement by polarization transfer (DEPT) and two-dimensional (2D) heteronuclear single quantum coherence (HSQC) and heteronuclear multiple bond correlation (HMBC) techniques. The structures of the complexes are confirmed by elemental analyses, MS, UV-Vis, FT-IR and H-1, C-13 NMR techniques. Redox behaviors of the ligand and its complexes have been investigated by cyclic voltammetry at the glassy carbon electrode in 0.1 M TBATFB in DMSO. The antibacterial activity was studied against Staphylococcus aureus ATCC 29213, Streptococcus mutans RSHM 676. Enterococcus faecalis ATCC 29212, Lactobacillus acidophilus RSHM 06029, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853. The antimicrobial test results indicate that all the complexes have low levels of antibacterial activity against both Gram negative and Gram positive bacterial species. (C) 2011 Elsevier Ltd. All rights reserved.
Synthesis, Enhanced Spectroscopic Characterization and Electrochemical Grafting of N-(4-Aminophenyl)aza-18-Crown-6: Application of Dept, Hetcor, Hmbc-Nmr and X-Ray Photoelectron Spectroscopy
(ELSEVIER, 2010) Deveci, Pervin; Taner, Bilge; Üstündağ, Zafer; Özcan, Emine; Solak, Ali Osman; Kılıç, Zeynel
This work describes the synthesis, characterization and electrochemical grafting of N-(4-Aminophenyl)aza-18-Crown-6 (4APA18C6). The key step in the synthesis is the reaction of N-phenylaza-18-crown-6 (PA18C6) with sodium nitrite. The compound, N-(4-nitrosophenyl)aza-18-crown-6 (NOPA18C6) could not be isolated purely from the reaction mixture, but a reduction of the residue with SnCl2 gave the desired aza-crown ether, N-(4-aminophenyl)aza-18-crown-6 (4APA18C6). To confirm its proposed structure detailed characterization techniques such as elemental analysis, FT-IR, H-1 NMR, C-13 NMR, DEPT, HETCOR, HMBC and ESI mass-spectrometry were used. Due to the importance of azacrown compounds in the field of analytical chemistry, in the derivatization of dyes, chemical sensors and ionic extraction, as molecular receptors, grafting of 4APA18C6 on the glassy carbon (GC) surface has been investigated by amine oxidation to gain new insight into the modification area. The oxidation mechanism has been established, and the results are in accordance with the attachment of amines to a glassy carbon surface by cyclic voltammetry. The modification of 4APA18C6 molecules onto the glassy carbon surface was verified by cyclic voltammetry (CV), X-ray photoelectron spectroscopy (XPS) reflection-absorption infrared spectroscopy (RAIRS) and ellipsometry. The film on the GC surface was formed according to the layer-by-layer mechanism and the ellipsometric thickness was obtained around 11.5 +/- 1.1 nm.

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