Person: SALAN, ÜMİT
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SALAN
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ÜMİT
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Publication Metadata only Synthesis, characterization, and electrochemical and in-situ spectroelectrochemical properties of novel peripherally and non-peripherally 7-oxy-3-(3,4-dimethoxyphenyl) coumarin substituted phthalocyanines(ELSEVIER SCI LTD, 2019) ÖZKAYA, ALİ RIZA; Feridun, Seda Gureli; Orman, Efe Baturhan; Salan, Umit; Ozkaya, Ali Riza; Bulut, MustafaNovel metal-free (4 and 9), Zn(II) (5 and 10) and Co(II) (6 and 11) phthalocyanines (Pcs) bearing four 7-oxy-3(3,4-dimethoxyphenyl)coumarin (1) substituents at peripheral (13) and non-peripheral (a) positions have been prepared by cyclotetramerization reactions of 4-(3-(3,4-dimethoxyphenyl)coumarin-7-oxy)phthalonitrile (3) or 3-(3-(3,4-dimethoxy-phenyl)coumarin-7-oxy)phthalonitrile (8), respectively, in the presence of relevant metal acetate salts in N,N-dimethylaminoethanol. The compounds have been characterized by elemental analysis, FTIR, UV-Vis and MALDI-TOF mass spectroscopies. Thermal properties of the compounds were evaluated by thermogravimetric analysis and differential scanning calorimetry. Electrochemical redox properties of all compounds were investigated by voltammetric and in-situ spectroelectrochemical measurements in dimethylsulfoxide including tetrabutyl ammonium perchlorate as the supporting electrolyte. The metal-free and Zn(II)Pc compounds displayed Pc ring-based redox processes whereas both Pc ring-based and metal-based electron transfer processes were observed for Co(II)Pc complexes. H-aggregation tendency of peripherally substituted compounds was found to be much higher than that of non-peripherally substituted ones. It was observed that there have been systemmatic redox potential and aggregation behaviour differences between the peripherally and non-peripherally substituted Pc compounds. These differences were attributed to different sterical and conformational effects of these substitution patterns. In-situ spectroelectrochemical and in-situ electrocolorimetric measurements suggested that peripherally substituted Co(II)Pc is a multi-coloured chromophore material displaying distinct spectral and colour changes during the first reduction and oxidation processes, and thus, being suitable for electrochromic applications.Publication Metadata only Novel lutetium(III) phthalocyanine-coumarin dyads; synthesis, characterization, photochemical, theoretical and antioxidant properties(ELSEVIER SCIENCE SA, 2021) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Koksoy, Baybars; Yalcin, Bahattin; Taskin, Turgut; Selcuki, Nursel Acar; Salan, Umit; Durmus, Mahmut; Bulut, MustafaIn this study, novel 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin substituted lutetium(III) phthalocyanine compounds were synthesized, characterized and their photochemical, theoretical, and antioxidant properties were examined. All complexes were characterized by common spectroscopic methods such as FT-IR, UV?vis, 1H NMR, MALDI-TOF-MS and elemental analysis as well. Geometry optimization of phthalocyanine compounds was calculated in the B3LYP functional using 6-31G (d, p) + SDD basis set of the Density Functional Theory. Aggregation, singlet oxygen generation, and photodegradation behavior under light irradiation of the complexes (1?4) were investigated in dimethylformamide. The three phthalocyanine compounds (1, 2, and 4) showed a high level of singlet oxygen efficiency were compared with the unsubstituted zinc(II) and lutetium(III) phthalocyanine compounds because their quantum yield values were found to be over 0.80. The radical cation scavenging activities of the compounds 3 (120.344 mM trolox/mg) and 4 (188.733 mM trolox/mg) are quite remarkable in 2,2?-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid analysis according to butylated hydroxyanisole (52.63 mM trolox/mg).Publication Metadata only The synthesis and fluorescence properties of novel chromenone-crown ethers(TAYLOR & FRANCIS LTD, 2010) SALAN, ÜMİT; Gunduz, Cihan; Salan, Uemit; Bulut, Mustafao-Dihyroxy-3-phenylchromenone derivatives, namely, 6,7-dihydroxy-3-(3',4'-dimethoxyphenyl)chromenone and 6,7-dimethoxy-3-(3',4'-dihydroxyphenyl)chromenone, were obtained from 2,4,5-trihydroxybenzaldehyde/3,4-dimethoxyphenylacetic acid and 2-hydroxy-4,5-dimethoxybenzaldehyde/3,4-dihydroxyphenylacetic acid, respectively, in the presence of acetic anhydride and sodium acetate under an inert atmosphere, after treatment with MeOH/HCl(aq). The chromenone-crown ethers were prepared from cyclic condensation of o-dihydroxy-3-phenylchromenones with poly(ethylene glycol) ditosylates in the presence of CH3CN/alkali metal carbonates. The chromatographically purified novel chromenone-crown ethers were identified by 1H NMR, MALDI-TOF mass spectrometry and elemental analysis. The fluorescence and UV-vis spectroscopic properties of the obtained chromenone-crown ethers and their complexes with Li+, Na+ and K+ perchlorate salts were estimated in acetonitrile. The quantum yields of novel chromenone-crown ethers were determined by the comparative method. [image omitted].Publication Metadata only 1,2,3-Triazole incorporated coumarin carrying metal-free, Zn(II), Mg(II) phthalocyanines: Synthesis, characterization, theoretical studies, photophysical and photochemical properties(ELSEVIER SCIENCE SA, 2020) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Abliatipova, Aziza; Benian, Sueda; Yalcin, Bahattin; Salan, Umit; Durmus, Mahmut; Bulut, MustafaIn this study, the preparation of two novel phthalonitrile compounds, 7-(propargyloxy)-3-(3,4-dicyanophenoxyphenyl)coumarin (1), and 7-(propargyloxy)-3-(2,3-dicyanophenoxy-phenyl)coumarin (2) were performed. Two new coumarinyl-1,2,3-triazole hybrids, (1-phenethy1-1H41,2,A-triazole 4 yl) 7 methyleneoxy 3 [F. (3,4 dicya nophenoxy)phenyl]-coumarin (3), and (1-phenethy1-1H-[1,2,3]-triazole 4 yl) 7 methyleneoxy 3 [F. (2,3 dicya nophenoxy)phenyl]-coumarin (4), were synthesized by the copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of 2-(azidoethyl)benzene with terminal ethynyl bearing coumarin derivatives (1 or 2). These novel phthalonitrile derivatives (3 and 4) were converted into their peripheral (5-7) and non-peripheral (8-10) metal-free, zinc(II) and magnesium(II) phthalocyanine counterparts. The synthesized phthalocyanine derivatives are first examples on the phthalocyanine-coumarin derivatives bearing triazole ring. The structures of all these novel compounds were characterized by variety of spectroscopic techniques including FT-IR, UV-vis, H-1 NMR, MALDI-TOF MS and elemental analysis. The photophysicochemical properties of all studied Pcs (5-10) were determined in dimethyl sulfoxide. The zinc(II) and magnesium(II) phthalocyanines bearing triazole containing coumarin substituents appear to be useful as Type II photosensitizers because the singlet oxygen quantum yields ranged in acceptable values from 0.17 to 0.49 confirmed that these phthalocyanines can be suggested as photosensitizers in Photodynamic Therapy applications. Geometry optimization, frequency analysis and molecular orbital energy values of coumarin/triazole substituted phthalocyanine were performed in Density Functional Theory method using the B3LYP/LANL2DZ level of theory.Publication Metadata only Synthesis and characterization of novel 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin substituted metallo phthalocyanines and investigation of their photophysical and photochemical properties(ROYAL SOC CHEMISTRY, 2019) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Karapinar, Begumhan; Yalcin, Bahattin; Salan, Umit; Durmus, Mahmut; Bulut, MustafaIn this study, the synthesis of novel 7-hydroxy-3-ethyl-6-hexyl-4-methylcoumarin (1), four respective phthalonitriles; 4-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (2), 3-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (3), 4-chloro-5-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (4), and 4,5-bis(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (5) and their corresponding alpha tetra, beta tetra and beta octa 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin and beta octa 4-chloro-5-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin) substituted Zn(ii) (6a-9a) and In(iii) Cl (6b-9b) phthalocyanines has been performed. The novel purified compounds were characterized by standard characterization techniques such as elemental analysis, thermal analysis, FT-IR, UV-vis, H-1-NMR and MALDI-TOF mass spectrometry. All of the obtained phthalocyanines showed lipophilic behaviour with excellent solubility in organic solvents such as acetone, dichloromethane, chloroform, pyridine and ethyl acetate. The fluorescence quenching behaviour was investigated using 1,4-benzoquinone and potassium iodide as quenchers. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen and photodegradation quantum yields) properties of these novel phthalocyanines (6a-9a and 6b-9b) were studied in DMF. They produced high singlet oxygen (for example phi(Delta) = 0.99 for 7b) and showed appropriate photodegradation (in the order of 10(-5)) which is very important for photodynamic therapy (PDT), and thus these phthalocyanines can be used as Type II photosensitizers in PDT applications.Publication Metadata only Synthesis, characterization and electrochemical properties of tetra 7-oxy-3-biphenylcoumarin substituted metal-free, zinc(II), cobalt(II) and indium(III) phthalocyanines(ELSEVIER SCI LTD, 2016) ÖZKAYA, ALİ RIZA; Gok, Asiye; Orman, Efe Baturhan; Salan, Umit; Ozkaya, Ali Riza; Bulut, MustafaA novel coumarin, 7-hydroxy-3-biphenylcoumarin 1, was prepared by Perkin reaction of 4-biphenylacetic acid with 2,4-dihydroxybenzaldehyde in the presence of NaOAc/Ac2O. In addition, two respective phthalonitril derivatives, 7-(2,3-dicyanophenoxy)-3-biphenylcoumarin 2/7-(3,4-dicyanophenoxy)-3-biphenylcoumarin 3, were synthesized by nucleophilic aromatic substitution reactions of 3-nitro/4-nitrophthalonitrile with 7-hydroxy-3-biphenylcoumarin 1. The synthesis of corresponding novel zinc(II) phthalocyanines (Pcs) 4 and 8, cobalt(II) Pcs 5 and 9, indium(III)(Cl) Pcs 6 and 10, and metal-free Pcs 7 and 11, carrying 7-oxy-3-biphenylcoumarins in the non-periphery/periphery was performed by cyclotetramerization of compounds 2 or 3. The novel chromogenic coumarin 1, phthalonitriles (2 and 3) and Pcs (4-11) were characterized by elemental and spectroscopic analysis, including H-1 NMR, FT-IR, UV-vis spectral and MALDI-TOF mass data. The redox properties of these compounds were also investigated by voltammetry and in situ spectroelectrochemistry on Pt in dimethylsulfoxide/tetrabutylammonium perchlorate. Furthermore, the electrocatalytic performances of the compounds for the oxygen reduction reaction were also studied. (C) 2016 Elsevier Ltd. All rights reserved.Publication Metadata only The synthesis and complexation study of some novel 3-methoxyphenyl chromenone crown ethers using conductometry(ELSEVIER SCI LTD, 2006) SALAN, ÜMİT; Gunduz, C; Salan, U; Ozkul, N; Basaran, I; Cakir, U; Bulut, M7,8-Dihydroxy-3-(3,4-dimethoxyphenyl)-2H-chromenoiies, 7,8-diliydroxy-3-(3,5-dimethoxyphenyl)-2H-chromenones and 7,8-dihydroxy-3-(3,4,5-trimethoxypheiiyl)-2H-chromenones, o-diliydroxy-3-iiiethoxyphenyicoumarins, were prepared from 2,3,4-trihydroxybenzaldehyde and corresponding methoxyphenylacetic acid in NaOAc/Ac2O, respectively. 3-Methoxyphenyl-7,8-dihydroxy-2H-chromenone reacted with the polyethylene glycol ditosylate or dichloride in CH3CN/alkali carbonate to afford [12]crown-4, [15]crown-5 and [18]crown-6-chromonones. The chromatographically purified novel chromenone crown ethers were identified with IR, H-1 NMR, 13 C NMR and low and high resolution mass spectroscopy and elemental analysis. Stability constants for the 1:1 complexes of Na+ and K+ with different substituted methoxyphenyl derivatives of coumarino[12]crown-4, coumarino[15]crown-5 and coumarino[18]crowti-6 (5a-5i) have been determined by conductometry at 25 degrees C in a binary solvent, dioxane/water. For all the coumarino crown ether derivatives, the stability constant decreases for K+ ion compared to Na+ ion. The selectivity sequence of these crown ethers in dioxane/water has showed an irregular order with respect to their cavity size. (c) 2005 Elsevier Ltd. All rights reserved.Publication Metadata only Synthesis and characterization of a new trans-2,2 '-azoquinoxaline bridged bisphthalocyanine(PERGAMON-ELSEVIER SCIENCE LTD, 2005) SALAN, ÜMİT; Salan, U; Altindal, A; Bulut, M; Bekaroglu, OA new trans-2,2'-azoquinoxaline bridged bisphthalocyanine was synthesized from the corresponding quinoxaline-2(1 H)one oxime, which can be obtained by the reaction of s-trans-chloroethanedial with 2-(3,4-diaminophenoxy)-9,16,23-tri(hexylthio)phthalocyanine zinc(II). 2-(3,4-Diaminophenoxy)-9,16,23-tri(hexylthio)phthalocyanine zinc(II) was synthesized by reduction of 2-(4-amino-3-nitrophenoxy)-9,16,23-tri(hexylthio)phthalocyanine zinc(II). Novel compounds were characterized by elemental analysis, UV/vis, IR and H-1 NMR spectroscopy. The conductivity and the humidity sensing properties of spin coated films of these compounds were investigated by measuring the complex impedance spectra at different humidities. Films of the final product show Up to 10(3) orders of magnitude higher conductivity than the starting and intermediate compounds. The results indicate that the presence of water vapour always leads to a drop in the real and imaginary part of the complex impedance. At room temperature, the capacitance of the films exhibits reversible increase with relative humidity, which makes these films attractive for humidity sensing applications. (c) 2005 Elsevier Ltd. All rights reserved.Publication Open Access The synthesis of novel 4-(3,4-dimethoxyphenyl)chromenone-crown ethers and their cation binding, as determined using fluorescence spectra(TAYLOR & FRANCIS LTD, 2009-12-01) SALAN, ÜMİT; Gunduz, Cihan; Salan, Umit; Bulut, MustafaThe complexation of naftifine (NF) and terbinafine (TB) with cyclodextrins (CDs) has been investigated by UV/visible and 1H NMR spectroscopy, ROESY techniques and also ESI-MS. Both drugs form 1:1 inclusion complexes with all the CDs tested except with -CD, as deduced from the Benesi-Hildebrand plots and confirmed by ESI-MS and NMR spectroscopy (Job plot method). The K11 values for NF decrease in the order -CDmethylated -CD2-hydroxypropyl--CD-CD. The determination of the enthalpy and entropy provides information about the main driving forces in the process. The stability constants of the complexes NF--CD, TB--CD and TB--CD determined by 1H NMR spectroscopy are in agreement with the values obtained by UV. For TB--CD, the value is higher, due to the fact that the length of the TB aliphatic chain allows a deeper inclusion of the naphthalene group inside the corresponding -CD molecule, according to the 2D ROESY experiments.Publication Metadata only EVALUATION OF ANTIOXIDANT, RADICAL-SCAVENGING AND ACETYLCHOLINESTERASE INHIBITORY ACTIVITIES OF VARIOUS CULINARY HERBS CULTIVATED IN SOUTHERN TURKEY(WILEY, 2014) OGAN, AYŞE; Danis, Ozkan; Yuce-Dursun, Basak; Cimen, Talin; Demir, Serap; Salan, Umit; Yalcin, Guler; Ogan, AyseThe purpose of this study was to determine the antioxidant, radical-scavenging, and acetylcholinesterase inhibitory capabilities of water and methanol extracts of Rhus coriariaL., Ocimum basilicumL., Rosmarinus officinalisL., Salvia officinalisL. and Thymbra spicataL., which are grown in the Hatay province of Turkey. Total antioxidant activities were evaluated using 2,2-diphenyl-1-picrylhydrazyl (22-782.6g/mL EC50),OH scavenging (3.93-33.43g/mL EC50), ferric (0.143-3.083mmol trolox equivalent (TE)/g), and cupric-reducing antioxidant power (0.143-3.083mmol TE/g) assays. The phenolic composition of the methanolic extract of R.coriaria leaves was also investigated, and the active compound was identified as 4-O-methylgallic acid. The highest IC50 value of acetylcholinesterase inhibitory activity (1.170.04mg/mL) was observed in R.coriaria leaves. Principal component analysis showed that R.coriaria leaves possessed greater antioxidant and anti-acetylcholinesterase potential as compared with the other evaluated plants. Practical ApplicationsAntioxidants are widely used in the food industry to prevent the formation of toxic oxidation products and prolong shelf life. Because of increasing concern among consumers about the use of synthetic antioxidants, there has been a great interest in the identification and use of natural antioxidants. The present study reveals that Rhus coriaria leaves, which are not commonly used in Mediterranean cuisine, are a promising source of natural antioxidants and could be considered as a potential source of anti-acetylcholinesterase agents and food preservatives. Both the antioxidant and anti-acetylcholinesterase effects of R.coriaria leaves may be beneficial in the treatment of Alzheimer's disease.