Person: YALÇIN, BAHATTİN
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YALÇIN
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BAHATTİN
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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 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 Çoklu metoksi fonksiyonel grupları içeren aza-BODIPY bileşiklerinin sentezi ve fotofizikokimyasal özellikleri(2022-09-28) ÖZDEMİR, MÜCAHİT; SALAN, ÜMİT; YALÇIN, BAHATTİN; KAZANCIÇOK Z., ÖZDEMİR M., SALAN Ü., YALÇIN B.Dipirometen ligandlarının bor atomu ile yaptığı kompleksler (bor-dipirrometen (BODIPY)) olarak adlandırılır. BODIPY bileşikleri görünür bölgede ışınları soğuran, floresans kuantum verimleri yüksek, ışık ve kimyasallara karşı dayanıklı floresans maddelerdir[1-2]. Aza-BODİPY bileşiklerinin fotofiziksel özelliklerinin, hücre boyama çalışmalarında ve fototerapi tedavi yönteminde ajan olarak kullanılmasının anlaşılması ile aza-BODİPY boyar maddelere olan ilgi artmıştır. Bu özelliklerinden dolayı BODİPY ve azaBODIPY bileşikleri, boyar maddeler arasında yer almaktadırlar [3]. Aza-BODİPY bileşikleri; ışık toplama sistemleri, enerji transfer kasetleri, boyar madde ile duyarlaştırılmış güneş pilleri, polimerler, lazer boyaları ve OLED uygulamalarında yüksek kuantum verimleri yüksek soğurma katsayısı ve bunların foto kararlılığı gibi özelliklerden yararlanılır. Ayrıca değişik alanlarda fotodinamik terapi (PDT) için ajan ve kemosensör gibi birçok uygulama alanı da bulunmaktadır [4]. Fotodinamik terapi, singlet oksijen üreten bir ışığa duyarlılaştırıcı (Ps) ve ışığın belirli dalga boylarını kullanan, kanseri tedavi etme yöntemlerinden biridir. İdeal bir ışığa duyarlılaştırıcı yüksek singlet oksijen üretebilmelidir. Singlet oksijen üretimi için kullanılan fotosensitizerlerin (PS) çoğu, porfirinlerden türetilen ortak bir siklik tetrapirolik yapıdan oluşur [5]. Buna ek olarak, literatürde rapor edilen birkaç porfirinik olmayan sistem, metilen mavisi, nil mavisi, nil kırmızısı, gül bengal ve karein boyalar gibi maddeler de singlet oksijen üreten maddelerdir. Bununla birlikte, bu tür PS sınıflarının dezavantajları, yakın kızılötesi (NIR) bölgede düşük molar absorpsiyon katsayıları ve karanlık toksisiteleridir. İdeal bir PS, iyi bir stabiliteye sahip olmalı ve λ=600–800 nm aralığında yüksek absorpsiyona sahip olmalıdır [6]. Bu çalışmada fenil halkaları üzerinden hidroksil ve metoksi grupları bulunduran azaBODIPY türevleri elde edildi. Elde edilen bu aza-BODIPY türevleri, brom ve iyot atomları ile ayrı ayrı sübstitüe edildi ve singlet oksijen üretme kapasitelerinin artırılması hedeflendi. Hedeflenen tüm bileşikler elde edilip saflaştırıldıktan sonra yapıları UV-Vis, FT-IR, 1H-NMR, MALDI-TOFF spektroskopi yöntemleriyle aydınlatıldı. Singlet oksijen üretiminin kuantum verimleri, absorpsiyon spektroskopisi yoluyla DPBF’nin foto-oksidasyonunun izlenmesiyle belirlendi.Publication Open Access Photophysical and photochemical properties and comparison of tolyl and tosyl coumarin-bearing phthalocyanines(2023-02-15) ÖZDEMİR, MÜCAHİT; YALÇIN, BAHATTİN; SALAN, ÜMİT; Kazancıçok Z., Güler H. E., ÖZDEMİR M., PİŞKİN M., Bulut M., YALÇIN B., SALAN Ü.© 2022In this study, peripheral and non-peripherally substituted Zn(II) phthalocyanine complexes were synthesized from 7‑hydroxy-3-(p-tolyl)coumarin and 7‑hydroxy-3-(p-tosyl)coumarin compounds. The synthesized new compounds were characterized using elemental analysis, FT-IR, UV–Vis, Fluorescence 1HNMR spectroscopy and MALDI-TOF mass spectrometry. All the synthesized phthalocyanine complexes showed good solubility in organic solvents such as acetone, dichloromethane, chloroform, pyridine, and ethyl acetate. Fluorescent quenching behavior was investigated using 1,4-benzoquinone and potassium iodide as a quencher. The photophysical (fluorescent quantum yields and lifetimes) and photochemical (single oxygen and photodegradation quantum yields) properties of these new phthalocyanines were examined in dimethyl sulfoxide. Phthalocyanine complexes containing 7‑hydroxy-3-(p-tolyl)coumarin had higher singlet oxygen quantum yields than phthalocyanine complexes containing 7‑hydroxy-3-(p-tosyl)coumarin. Phthalocyanines to which coumarins are peripherally bound were more advantageous than their non-peripherally bound derivatives. As a result of their photophysical and photochemical properties, coumarin-phthalocyanine complexes containing tolyl-/tosyl- groups can be used as photosensitizing candidates in photodynamic therapy and can be developed with targeted modifications.Publication Metadata only Phthalocyanines bearing silazane group for colorectal cancer(ELSEVIER SCI LTD, 2021) GÖRGÜLÜ, AHMET ORHAN; Ozdemir, Mucahit; Artuc, Gamze Ozgul; Guler, Eray Metin; Yalcin, Bahattin; Salan, Umit; Bozali, Kubra; Gorgulu, Ahmet Orhan; Bulut, MustafaThe synthesis of bis(trimethylsilyl)amine substituted zinc(II), and indium(III) chloride phthalocyanine complexes have been performed. The obtained compounds were characterized by spectroscopic methods. All synthesized phthalocyanine derivatives were evaluated for cytotoxic, genotoxic, and apoptotic activities on LoVo cell lines which are the standard colorectal cancer cell lines derived from metastatic site: left supraclavicular region. Nonperipheral silazane substituted zinc phthalocyanine (5) showed quite different behavior from all the other compounds analyzed and found to be the best cytotoxic, genotoxic, and apoptotic compound. All derivatives showed no proliferative effect at all doses. All phthalocyanine compounds increased cytotoxicity, DNA damage, apoptosis, and intracellular ROS dose-dependent manner. To explain and verify in vitro tests, phthalocyanine compound structures were optimized using density functional theory, and in silico molecular docking studies on B-DNA dodecamer were performed. Both the experimental and theoretical findings comply with each other.Publication Metadata only 7-Oxy-3,4-cyclohexenecoumarin Carrying Novel Zinc(II) and Indium(III) Acetate Phthalocyanines: Synthesis, Characterization, Photophysical and Photochemical Properties(WILEY-V C H VERLAG GMBH, 2019) YALÇIN, BAHATTİN; Karapinar, Beguemhan; Oezdemir, Muecahit; Salan, Uemit; Durmus, Mahmut; Yalcin, Bahattin; Bulut, MustafaIn this study, 7-hydroxy-3,4-cyclohexenecoumarin (1), two new phthalonitriles, 7-(2,3-dicyanophenoxy)-3,4-cyclohexene-coumarin (2), 7-(3,4-dicyanophenoxy)-3,4-cyclohexenecoumarin (3), were prepared. The phthalonitrile derivatives 2 and 3 were converted to the respective non-peripheral tetra, peripheral tetra 7-oxy-3,4-cyclohexenecoumarin substituted zinc(II) (4,6) and indium(III)acetate phthalocyanine (5,7) derivatives. All novel purified compounds (2-7) were characterized by elemental analysis, FT-IR, UV-vis, (HNMR)-H-1, 13CNMR, MALDI-TOF mass data. The spectral, photophysical (fluorescence quantum yields and lifetimes), and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of the synthesized Pcs (4-7) were studied in DMF, and the results were compared to determine the effects of the locations of substituents and the diversity of the central metal atom on these properties. The 7-oxy-3,4-cyclohexenecoumarin bearing phthalocyaninatozinc(II) and indium(III)acetate complexes showed good solubility in organic solvents such as chloroform, dichloromethane, tetrahydrofuran, acetone, DMF and DMSO. The fluorescence quenching behavior were investigated using 1,4-benzoquinone as a quencher. They have an acceptable level of singlet oxygen production, which determines the usability of phthalocyanines in photodynamic therapy applications and demonstrated appropriate photodegradation. The thermal properties of Pcs (4-7) were also investigated.