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Güncel Gönderiler
Öğe Effects of Heavy Iodine Atoms and ?-Expanded Conjugation on Charge Transfer Dynamics in Carboxylic Acid BODIPY Derivatives as Triplet Photosensitizers(2023) Akhüseyin-Yıldız, Elif; Yabaş, Ebru; Sözmen, Fazlı; Bozkurt, Yasemin; Karatay, Ahmet; Boyacıoğlu, Bahadır; Ünver, Hüseyin; Elmalı, AyhanBorondipyrromethene (BODIPY) chromophores are composed of a functional-COOH group at meso position with or without a biphenyl ring, and their compounds with heavy iodine atoms ... .Öğe Two-Photon Absorption Response of Functionalized BODIPY Dyes in Near-IR Region by Tuning Conjugation Length and Meso- Substituents(2023) Akhüseyin-Yıldız, Elif; Ünlü, Bekir Asilcan; Karatay, Ahmet; Bozkurt, Yasemin; Özler, Muhammed Emre; Sözmen, Fazlı; Yabaş, Ebru; Boyacıoğlu, Bahadır; Ünver, Hüseyin; Elmalı, AyhanBODIPY dyes substituted by phenol or −COOMe units at the meso-position (C8) with and without a distyryl group including a methoxy moiety at the -C3 and -C5 positions of the BODIPY have been synthesized to analyze the photophysical properties. To clarify the ground-state interaction, absorption and emission features were investigated in the THF environment. Extending the π-conjugation with the methoxy moiety at -C3 and -C5 positions of BODIPY leads to a spectral shifting of the absorption maxima toward red by 120 nm. In addition, attaching the −COOMe unit at the meso-position of the BODIPY structure increases nonradiative molecular relaxation as compared to compounds possessing phenol substituents at the same position. We have investigated the effect of phenol and a −COOMe group and π-extended conjugation length with a methoxy moiety on the properties of two-photon absorption (TPA) and electron transfer dynamics by performing open-aperture (OA) Z-scan and femtosecond transient absorption spectroscopy measurements, respectively. The synthesized BODIPY compounds with the distyryl group including the methoxy unit show TPA character due to the longer conjugation length and therefore intramolecular charge transfer ability. Based on the OA Z-scan experiments upon photoexcitation with 800 nm pulsed laser light, TPA cross-section values were obtained as 74 and 81 GM for the compounds possessing phenol and −COOMe units at the meso-position of BODIPY treated by distyryl group with methoxy moieties, respectively. Additionally, optical and electronic properties were calculated theoretically by using the DFT method.Öğe Novel reduced graphene oxide/zinc phthalocyanine and re duce d graphene oxide/cobalt phthalocyanine hybrids as high sensitivity room temperature volatile organic compound gas sensors(2023) Yabaş, Ebru; Biçer, Emre; Altındal, AhmetIn this work, novel 4-pyridynyl-oxadiazole tetrasubstituted zinc and cobalt phthalocyanine compounds were synthesized and characterized by UV-vis, Fluorescence spectroscopy, and SEM. Then these com- pounds were mixed with reduced graphene oxide. As a result of the interaction of these newly syn- thesized phthalocyanines with reduced graphene oxide (rGO), rGO/ZnPc and rGO/CoPc hybrids were ob- tained. The measurement results confirm that the prepared non-covalent rGO/ZnPc and rGO/CoPc hybrid structures are formed by strong π–πinteraction. A comparative study of the sensor response of rGO and non-covalently functionalized with zinc and cobalt phthalocyanines (rGO/ZnPc, and rGO/CoPc) hybrids to five different volatile organic compound vapors, ammonia, acetone, ethanol, methanol and butanol is car- ried out. The response of the sensors increases with respect to ammonia concentrations ranging from 30 to 210 ppm. The response time for 120 ppm ammonia vapor were approximately 250s, 230s and 190s for rGO, rGO/ZnPc, and rGO/CoPc based sensors, respectively. Also, we have conducted selectivity exper- iments with the aformentioned vapors, thus, studies have indicated that functionalization of rGO with ZnPc results in a 43-fold improvement in sensor response towards ammonia vapors.Öğe A comprehensive archaeometric analysis of a novel special organic finding in a glass unguentarium: NMR, FT?IR, SEM/EDX(2023) Pehlivan, Erdener; Yabaş, Ebru; Özer, AliIn this study, systematical analyses were employed to determine that which period the historical artifact belonged, and evaluations were based on the glass-making technology of the period. In addition, since organic substances were carried in these glass bottles, they are likely to be the medicine or ornaments at that time; by using recently developed techniques as NMR, SEM– EDX and interpret them in the correct way, it was possible to predict what the yellow oily looking organic substance might be in. As the mouth of the glass bottle is completely closed with clay, the characterization of this organic material was made on the clay sample taken from the underneath of the environment without damaging the historical artifact. The trace organic matter residues on the clay were isolated and characterized by NMR spectrometry; this sample was characterized with FT-IR. Finally, the surface morphology of the clay–oil mixture was examined morphologically with SEM, and with EDX, elemental analysis was performed. In the results obtained, it was concluded that the organic material in the historical artifact could be olive oil with a high content of palmitic acid. With this study, the content of the artifact could be clarified by making a structural examination of the remains without damaging the historical artifact.Öğe The new soluble tetra-substituted oxo-titanium phthalocyanines: Synthesis, characterization, spectral and colorimetric pH sensing properties(Journal of Molecular Structure, 2023) Yabaş, EbruNew imidazole tetrasubstituted oxo-titanium phthalocyanine 1 was synthesized by tetramerization reac- tion of imidazole substituted phthalonitrile in the presence of titanium(IV) butoxide. N-alkylated imida- zole tetrasubstituted oxo-titanium phthalocyanine 2 was prepared by N-alkylation reaction of compound 1 with iodomethane in basic medium. Afterwards, as a result of the quaternization reaction of compound 2 , water-soluble oxo-titanium phthalocyanine 3 was prepared. The synthesized compounds were charac- terized by UV-Vis, FT-IR, 1 H-NMR, MALDI-TOF MS and elemental analysis. The spectral properties, surface morphologies in powder form and thin films, colorimetric pH sensing properties and aggregation behav- iors of the synthesized compounds were investigated. We also used the UV-Vis spectroscopy technique to experimentally find the optical band gap of compound 1 with the best thin-film surface properties. In this context, transmittance, absorption and band gap energy of compound 1 thin film were investigated.Öğe Toghrul Almammadovb(2022) Ebru YABAŞ; Safacan Kölemen; Emre Biçer; Toghrul Almammadov; Pınar Başer; Mehmet KulIn this study, the spectroscopic measurements of the second generation dendritic zinc phthalocyanine (phthalocyanine dendrimer with tris) 2 were made and its potential to be used in optoelectronic applications was investigated. To examine the intramolecular energy transfer properties, fluorescence quantum yields were calculated and the contribution of first (phthalocyanine dendrimer with triethyl methanetricarboxylate) 1 and second 2 generation dendrimers to this energy transfer was investigated. The photoluminescence properties and optical band gap of the second generation zinc phthalocyanine 2 were investigated depending on the temperature. In addition, the quantum efficiency of singlet oxygen was calculated to evaluate the usability of this compound in photodynamic therapy. Also, aggregation behavior of compound 2 was examined in different solvents (DMF, DMSO and THF) and different concentrations in THF. To the best of our knowledge, this is the first study to examine the photoluminescence properties and temperature dependent changes of dendritic phthalocyaninesÖğe New water soluble magnesium phthalocyanine as a potential anticancer drug: Cytotoxic and apoptotic effect on different cancer cell lines(2022) Ebru YABAŞ; Serap Şahin Bölükbaşı; Zeynep Deniz Şahin İnanAlthough phthalocyanines are usually used a photosensitizers for photodynamic therapy, these works focus on the directly cytotoxic effect of a new water-soluble magnesium phthalocyanine. The new water-soluble magnesium phthalocyanine 2 was synthesized, characterized and investigated for cytotoxic and apoptotic activities. The cytotoxic activities of the compound 2 were determined by using (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) cell viability assay on human breast cancer cells (MDA-MB-231, MCF-7), human prostate cancer cells (PC-3), and human healthy lung fibroblast cells (WI-38). The cells were plated and treated 1 to 20 mM of different concentrations of the compound. MTT assay results indicated that the compound 2 has concentration and time-dependent cytotoxic activities against cancer cells. We also observed that the compound displayed lower toxicity against WI-38 healthy cells than cancer cells at 48 and 72 h. The compound showed a significant cytotoxic activity difference between breast cancer cells and WI-38 healthy cells at 48 and 72 h. Selectivity index of the compound 2 against MCF-7 for 72 h was calculated >15.62. We also studied the apoptotic and necrotic effect of compound 2 using TUNEL and PI staining, respectively. It was found that the synthesized compound 2 increased apoptotic and necrotic cells.Öğe Double-decker lutetium and europium phthalocyanine composites with re duce d graphene oxide as supercapacitor electrode materials(2022) Ebru YABAŞ; Emre Biçer; Mete Batuhan Durukan; Deniz Keskin; Husnu Emrah UnalanDouble-decker phthalocyanines were synthesized by a classical method with phthalonitrile and lan- thanide metal salts, europium and lutetium acetate. Non-covalent double-decker phthalocyanine-reduced graphene oxide (MPc 2 /rGO) composites were then prepared by simple sonication method. All the ph- thalocyanines were peripheral tetrasubstituted 5-(3-pyridyl)-1,3,4-oxadiazole. Following spectroscopic and morphological characterisation, fabricated composites were subjected to detailed electrochemical analy- sis. EuPc 2 /rGO and LuPc 2 /rGO composite electrodes showed specific capacitance values of 115 F/g and 86 F/g, respectively. Coulombic efficiency values for those materials were determined as 85% and 74%, respectively, at a significant current density of 5 A/g. Following 50 0 0 cycles, EuPc 2 /rGO and LuPc 2 /rGO electrodes retained 93% and 99% of their initial capacitance, respectively. These results demonstrated the significant electrochemical performance of double-decker phthalocyanines and can be certainly extended to other metal salts or other composite formers with double-decker phthalocyanines.Öğe New cobalt phthalocyanine–graphene oxide hybrid nanomaterial prepared by strong ?–? interactions(2022) Yabaş, EbruIn this study, a novel hybrid nanomaterial was obtained by interaction of cobalt phthalocyanine (CoPc) derivative on the surface of graphene oxide (GO) producing a CoPc-GO supermolecular system in which interaction is occurred by the π–π stacking. The CoPc-GO hybrid was prepared in a much shorter time than the examples in the literature, and it was observed that this nanomaterial was quite stable at room conditions and during dilution. The obtained hybrid nanomaterial was analyzed by scanning electron microscopy (SEM) and spectroscopic methods. Spectroscopic measurements indicate that immediate intermolecular interactions are occurring during the mixing of GO and CoPc. SEM studies show that CoPc successfully interacts with GO. Significant color changes were also observed by the addition of GO solutions at different concentrations on the CoPc solution. Also, we determined the optical band gap of the CoPc-GO nanohybrid using UV–Vis spectroscopy technique. It was also determined that the stable CoPc-GO hybrid, which can be prepared very quickly and easily, has the potential to be used in optoelectronic applicationsÖğe Experimental and In Silico studies on optical properties of new thiadiazole tetrasubstituted metal-free and zinc phthalocyanine compounds(2021) Yabaş, EbruIn this study, 2-amino-5-phenyl-1,3,4-thiadiazole substituted metal-free phthalocyanine (H2Pc) was synthesized by tetramerization reaction of the phthalonitrile derivative. The synthesized compound was characterized by IR, UV–Vis, 1H NMR, MS spectroscopy and elemental analysis. To determine the potential of the synthesized phthalocyanines to be used in optical applications (thiadiazole substituted metal-free and zinc(II) derivatives), photoluminescence and fluorescence properties of compounds were studied. In addition, the powder and thin film surface morphology of these compounds were examined by scanning electron microscope (SEM). The electronic features (chemical hardness, electron affinity, electronegativity) and frontier orbital energy levels (HOMO-LUMO) were computed using density functional theory. The HOMO-LUMO energies of (H2Pc) and zinc(II) phthalocyanine (ZnPc) were acquired close to each other. The spectroscopic studies showed that the UV–visible spectra obtained using time-dependent density functional theory (TDDFT) was compatible with the experimental UV–visible study. The nonlinear optical (NLO) results indicated that the NLO properties of H2Pc are slightly better than ZnPc.
