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Öğe Azaindole-BODIPYs: Synthesis, fluorescent recognition of hydrogen sulfate anion and biological evaluation(Pergamon-Elsevier Science Ltd, 2019) Kesan, Gurkan; Topaloglu, Burcu; Özcan, Emrah; Kazan, Hasan Huseyin; Ecik, Esra Tanriverdi; Şenkuytu, Elif; Cosut, Bunyemin; Kandemir, HakanThe synthesized and sensing capability of two novel azaindole substituted mono and distyryl BODIPY dyes against bisulfate anion were reported. Structural characterizations of the targeted compounds were conducted by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, H-1 and C-13 NMRspectroscopies. Photophysical properties of the azaindole substituted BODIPY compounds were investigated employing absorption and fluorescence spectroscopies in acetonitrile solution. It was found that the final compounds 3 and 4 exhibited exclusively selective and sensitive turn-off sensor behavior on HSO4- anion. Additionally, the stoichiometry ratio of the targeted compounds to bisulfate anion was measured 0.5 by Job's method. Also, density function theory was performed to the optical response of the sensor for targeted compounds. Furthermore, the cytotoxicity of Azaindole-BODIPYs was examined against living human leukemia K562 cell lines. (C) 2019 Elsevier B.V. All rights reserved.Öğe Experimental and theoretical studies of carbazole-based Schiff base as a fluorescent Fe3+ probe(Scientific Technical Research Council Turkey-Tubitak, 2018) Kandemir, Hakan; Koçak, Abdulkadir; Tumay, Süreyya Oguz; Cosut, Bunyemin; Zorlu, Yunus; Şengül, İbrahim FazılSynthesis of a new (E)-N1-((9-ethyl-9H-carbazol-3-yl)methylene)-5-nitrobenzene-1,2-diamine as a fluorescent chemosensor for selective detection of Fe3+ ion over a number of other metal ions is described. The method for the synthesis of the carbazole Schiff base was based on the condensation of carbazole-3-carbaldehyde with 4-nitro-o-phenyldiamine in dimethylformamide in a moderate yield. The structure of the final compound was characterized by H-1 NMR, (13) C NMR, IR, mass spectrometry, and single crystal X-ray diffraction. The final compound exhibited exceptional selective and sensitive turn-on fluorescence response to the Fe3+ cation. The fluorescent intensity of the final compound was increased 20-fold and the stoichiometry ratio of the final compound to Fe3+ was 1:1. The association constant and detection limit for Fe3+ ion were predicted from fluorescence titrations as (1.36 +/- 0.09).10(4) M-1 and 1.0 to 6.0 mu M, respectively. The photophysical behavior of the compound was further explored by DFT methods. The predicted UV-Vis spectrum by TDDFT calculations was compared to the observed absorption spectrum of the targeted compound.Öğe Light harvesting systems composed of carbazole based subphthalocyanine-BODIPY enhanced with intramolecular fluorescence resonance energy transfer (FRET)(Elsevier Sci Ltd, 2017) Ecik, Esra Tanriverdi; Özcan, Emrah; Kandemir, Hakan; Şengül, İbrahim Fazıl; Cosut, BunyeminA new series of subphthalocyanine-borondipyrromethene scaffolds containing N-ethylcarbazole moiety have been successfully designed and synthesized. The identities of synthesized compounds were confirmed by using H-1, C-13 NMR, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The photophysical properties of the newly synthesized subphthalocyanine-borondipyrromethene conjugates were investigated via absorption and fluorescence spectroscopies in dichloromethane, tetrahydrofuran, benzene, and toluene solution (1 x 10(-5) M). The targeted compounds exhibit a highly efficient energy transfer process, either from the excited borondipyrromethene to the subphthalocyanine core or from the excited subphthalocyanine to the mono or distyryl borondipyrromethene unit. The time resolved fluorescence studies of the subphthalocyanine-borondipyrromethene conjugates were also examined. (C) 2016 Elsevier Ltd. All rights reserved.Öğe Meso carbazole linked Bis-BODIPYs: Design, synthesis, structures and properties(Pergamon-Elsevier Science Ltd, 2023) Aksoy, Burcu Topaloglu; Senocak, Ahmet; Erol, Ismail; Saglam, Mehmet F.; Kandemir, Hakan; Sengul, Ibrahim F.; Cosut, BunyeminIn the present study, BODIPY 4 bearing carbazole ring system at meso position was successfully synthesized as a key building block by the acid-catalyzed condensation reaction of 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde 3 with 2,4-dimethylpyrrole in one step. The Suzuki and Stille coupling synthetic strategies were subsequently applied to the compound 4 for the construction of a new class of bis-BODIPYs 5 and 6 with extended pi-conjugation by introducing phenyl and bithiophene as linkers between two N-ethylcarbazole units. The structures of novel compounds 4-6 were identified by mass, 1H and 13C NMR spectroscopy along with single crystal X-ray diffraction techniques. The photo-physical features of the targeted BODIPYs were investigated via absorption and fluorescence spectroscopies in solvents with different polarity. Photophysical studies reveal important transitions between carbazole and BODIPYs in solution state, which could be controlled by solvent polarity. Crystal geometry of the molecules and the optical band gaps were supported by DFT calculations. Electrochemical and in situ spectroelectrochemical properties of the synthesized compounds were also investigated to reveal electropolymerizable properties and electrochromic potentials of the targeted materials. The results suggested that the compounds 5 and 6 can be potentially used as useful materials in a range of electrochemical research areas.Öğe Meso-piperidine linked bodipys: Synthesis, fluorescent properties and biological evaluation(Elsevier Science Bv, 2019) Ecik, Esra Tanriverdi; Kazan, Hasan Huseyin; Şengül, İbrahim Fazıl; Kandemir, Hakan; Cosut, BunyeminThe synthesis and characterization of meso-piperidine linked Bodipy starting from 4-(2-(piperidine-1-yl)ethoxy) benzaldehyde was described. Meso-piperidine linked Bodipy was subsequently used for the construction of distyryl-piperidine-Bodipy and distyryl-morpholine-Bodipy via Knoevenagel type reaction. The photophysical properties including molar extinction coefficient, fluorescence lifetime and fluorescence quantum yield of Bodipys were investigated in ethanol solution. The targeted compounds were also assessed in live cell imaging and cytotoxicity studies by using breast cancer cell line, MCF-7 in vitro.
