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Öğe A BODIPY decorated multiple mode reusable paper-based colorimetric and fluorometric pH sensor(Elsevier, 2022) Ozturk, Dilek; Omeroglu, Ipek; Gol, Cem; Durmus, MahmutIn this study, two difluoroboradiazaindacene (BODIPY) compounds bearing diethylaminostyryl groups were synthesized in order to establish colorimetric and fluorometric paper-based pH sensors. The structures of these novel BODIPY compounds were identified by NMR (H-1, C-13, B-11, and F-19), elemental analysis, MALDI-TOF, FT-IR, UV-vis and fluorescence spectroscopies as well as single-crystal X-Ray data. The DFT study was also per-formed to optimize of these two novel BODIPY structures. Electrochemical measurements were applied to estimate their redox potentials. Photophysical properties such as fluorescence quantum yield and lifetimes were investigated to determine the effect of acid addition in both DMSO and 1,4-dioxane solutions of the studied BODIPY derivatives. Also, pKa values of the synthesized compounds (1a and 1b) were determined from absorbance and fluorescence measurements by acid titration studies. The paper-based pH sensor behavior of these BODIPY derivatives was investigated and their performances were determined on the lemon juice samples as a real sample analysis. A simple, cost-effective, rapid, portable, colorimetric, and fluorometric paper-based BODIPY sensing platform was developed in this study for the detection of the variety of pH changes in lemon juice.Öğe Direct Photopatterning of BODIPY-Based Small Molecules via Thiol-ene Click Chemistry(Wiley-V C H Verlag Gmbh, 2023) Ozdemir, Mucahit; Altinisik, Sinem; Omeroglu, Ipek; Koksoy, Baybars; Durmus, Mahmut; Yalcin, Bahattin; Koyuncu, SermetWe demonstrate a BODIPY-based small molecule photopatterned surface by thiol-ene click chemistry at room temperature utilizing only 366 nm UV light. The resulting cross-linked polymer exhibits porous surfaces according to AFM and TEM results. A dramatic blue shift occurred in absorption spectra and the photoluminescence was also intensified as a result of crosslinking. Optical and electrochemical results are compatible with the DFT calculations. The obtained results prove that the photopatterned BODIPY-based material can be easily and inexpensively applied in multilayer optoelectronic devices.Öğe Electron-Donating and Electron-Withdrawing Subunit Effects on Coumarin-BODIPY Dyads: Optical and Electrochemical Properties and Molecular Interactions(Wiley-V C H Verlag Gmbh, 2023) Koksoy, Baybars; Ozdemir, Mucahit; Altinisik, Sinem; Zorlu, Yunus; Yalcin, Bahattin; Durmus, Mahmut; Koyuncu, SermetIn this study, a series of coumarin-BODIPY molecules were synthesized using a Sonogashira cross-linking reaction. The effects of electron withdrawing and electron donating moieties on electrochemical and optical properties were supported by results of density functional theory calculations, and energy transfer mechanisms were investigated. The band gap value decreased from 2.0 eV to 1.6 eV due to reversible oxidation of the extra dimethylamino subunit at lower potential. Besides, characteristics of the crystal structures were investigated with single-crystal X-ray diffraction, and crystallinity was supported by differential scanning calorimetry. In addition, when the thin film surface morphologies were examined, it was clearly observed that the N,N-dimethylamino group on the coumarin-BODIPY dyad (B3) formed large-scale domains due to its crystalline behavior. As a result, Forster-type energy transfer was observed for coumarin-BODIPY dyads containing different electron withdrawing and donating subunits.Öğe Investigating the Photochemical Properties of a Clickable Silicon (IV) Phthalocyanine Core(Wiley-V C H Verlag Gmbh, 2025) Ozdemir, Mucahit; Sevimli, Esra; Ozturkkan, Fureya Elif; Durmus, Mahmut; Yalcin, Bahattin; Koksoy, BaybarsIn this study, a new azido-functionalized silicon(IV) phthalocyanine (SiPcN3) was synthesized and comprehensively characterized, revealing its promising photochemical characteristics. Despite the common challenges associated with crystallizing phthalocyanine-based compounds, SiPcN3 was successfully obtained as single crystals in the monoclinic P21/c space group. The incorporation of -N3 groups not only enhanced the compound's solubility and thermal stability but also introduced a reactive site suitable for future functionalization via copper-catalyzed azide-alkyne click chemistry. The molecular design enables straightforward integration into extended macromolecular systems, such as covalent organic frameworks (COFs) or cross-linked polymers. UV-Vis and photoluminescence analyses demonstrated intense Q-band absorption in the red region and tunable emission characteristics. The measured singlet oxygen quantum yield (Phi Delta = 0.14) indicates moderate photosensitizing activity, but this performance can potentially be enhanced through appropriate derivatization, improving its applicability in photodynamic therapy (PDT). Overall, these findings position SiPcN3 as a structurally versatile and functionally adaptable molecular platform, with promising potential for future development of PDT agents, photocatalytic/photooxidative materials, and optoelectronic devices, especially when embedded into porous or cross-linked polymeric networks.Öğe New metallophthalocyanines including benzylphenoxy groups and investigation of their organic-field effect transistor (OFET) features(Elsevier Sci Ltd, 2022) Ozdemir, Mucahit; Altinisik, Sinem; Koksoy, Baybars; Canimkurbey, Betul; Koyuncu, Sermet; Durmus, Mahmut; Yalcin, BahattinIn this study, metal and metal-free novel phthalocyanines containing peripheral and non-peripheral tetra 2-ben-zylphenoxy groups were synthesized. The compounds were characterized by UV-Vis, FT-IR, H-1 NMR, and MALDI-TOF mass spectrometry as well as elemental analysis. These new phthalocyanines exhibited excellent solubility in most organic solvents, and their redox behavior was investigated in different solvents such as dimethyl sulfoxide (DMSO) and dichloromethane (DCM). The redox behavior of the peripheral and non-peripheral phthalocyanine compounds 1a -c and 2a -c was determined by cyclic voltammetry and in situ spec-troelectrochemistry. According to organic field-effect transistors (OFETs) measurements, the peripheral and non-peripheral phthalocyanine-cobalt complexes which have higher mobility than others were utilized top-gate bottom-contact OFETs fabrication. The output characteristics of the device show that its mobility is approximately 5 x 10(-2) cm(2)/Vs with p-type accumulation.Öğe Novel SWCNT-hybrid nanomaterial functionalized with subphthalocyanine substituted asymmetrical zinc (II) phthalocyanine conjugate: Design, synthesis, characterization and sensor properties for pesticides(Elsevier Science Sa, 2021) Köksoy, Baybars; Akyuz, Duygu; Senocak, Ahmet; Durmus, Mahmut; Demirbas, ErhanThe novel asymmetric zinc (II) phthalocyanines containing one ethyloxy azido and three iodine (Iodo-Pc) or subphthalocyanine (SubPc-Pc) groups were designed and synthesized for the first time. These novel phthalocyanines were chemically characterized by common spectral methods such as FT-IR, UV-vis, H-1-NMR,C- 13-NMR and MALDI-TOF mass spectroscopy and elemental analyses as well. Furthermore, a novel hybrid carbon nanomaterial (SWCNT-SubPc-Pc) bearing subphthalocyanine substituted zinc (II) phthalocyanine conjugate on the single walled carbon nanotube (SWCNT) surface was also prepared via azide-alkyne Huisgen cycloaddition (click) reaction. This novel hybrid carbon nanomaterial was chemically characterized by UV-vis, FT-IR and Raman spectroscopies. The thermal behaviour of the prepared SWCNT-SubPc-Pc was characterized by thermogravimetric analysis. Surface morphologies of the hybrid material were also investigated by scanning and transmission electron microscopies. SWCNT-SubPc-Pc hybrid nanomaterial was successfully modified on glassy carbon electrode (GCE) by using drop cast method. Then, the GCE/SWCNT-SubPc-Pc electrode was tested as pesticide sensor via electrochemical methods. The electrochemical responses were recorded using differential pulse (DPV) and cyclic voltammetries. The modified electrode acted as selectively to methyl parathion among the used pesticides (methyl parathion, acetamiprid and chlorantraniliprole). The electrochemical sensor behaviour exhibited a broad linear range (2.5 nM and 3.75 x 10(-8) M) and low detection limit (1.78 nM) for methyl parathion. Moreover, high performance liquid chromatography was used to validate the results obtained from orange and cherry juice samples with respect to the DPV results.Öğe Photophysicochemical and electrochemical properties of pyrene-BODIPY platforms(Royal Soc Chemistry, 2024) Omeroglu, Ipek; Koksoy, Baybars; Ozturk, Dilek; Salah, Lubna; Maksheed, Saad; Durmus, MahmutThe photochemical, photophysical, and electrochemical properties of BODIPY compounds (1-7) substituted with iodine or pyrene at the 2-, 6-, or 8-positions (meso) were thoroughly investigated in this study. Through the incorporation of iodine and/or pyrene moieties into the BODIPY derivatives, we evaluated their impact on the photophysical properties using both steady-state and time-resolved fluorescence analyses. Notably, the heavy atom effect induced by iodine was observed, leading to an increase in singlet oxygen quantum yield in proportion to fluorescence intensity. Furthermore, the introduction of pyrene at the meso position in BODIPY (compound 5) significantly enhanced the pi-conjugated system and facilitated the generation of singlet oxygen. Intriguingly, compound 7, which featured pyrene substitutions at positions 2, 6, and 8, exhibited a reduced singlet oxygen yield when compared to the iodine-substituted compound 6. Moreover, we conducted an evaluation of the electrochemical properties of the BODIPY compounds (1-7) in dichloromethane. Additionally, we characterized the structures of the synthesized compounds (5 diamond , 6, and 7) using various spectroscopic techniques, including FT-IR, HRMS, and NMR (1H, 13C, 19F, and 11B), which were performed for the first time within the scope of this study. The comprehensive findings obtained from this extensive research contribute valuable knowledge that has the potential to guide the development of highly efficacious photosensitizers for applications in photodynamic therapy. The photochemical, photophysical, and electrochemical properties of novel BODIPY compounds substituted with iodine or pyrene groups at the 2-, 6-, or 8-positions (meso) were thoroughly investigated.Öğe Sensitive, simple and fast voltammetric determination of pesticides in juice samples by novel BODIPY-phthalocyanine-SWCNT hybrid platform(Pergamon-Elsevier Science Ltd, 2021) Köksoy, Baybars; Akyuz, Duygu; Senocak, Ahmet; Durmus, Mahmut; Demirbas, ErhanThe present work describes the first synthesis of novel asymmetric zinc (II) phthalocyanine (ZnPc) including three boron dipyrromethene (BODIPY) and one ethyloxy azido moieties. Moreover, single walled carbon nanotube (SWCNT) surface was functionalized by this ZnPc containing BODIPY; using the azide-alkyne Huisgen cycloaddition (Click) reaction to obtain SWCNT-ZnPc hybrid material. Structural, thermal and morphological characterizations of both ZnPc and SWCNT-ZnPc hybrid were carried out in-depth by spectroscopic, thermal and microscopic techniques. In this study, the synthesized SWCNT-ZnPc material was decorated on composite glassy carbon electrode (GCE) by means of an easy and a practical drop cast method. The modified electrode was tested as a non-enzymatic electrochemical sensor in various common pesticides such as methyl parathion, deltamethrin, chlorpyrifos and spinosad. Electrochemical behavior of non-enzymatic electrode (GCE/SWCNT-ZnPc) was determined via cyclic voltammetry and differential pulse voltammetry. The non-enzymatic sensor demonstrated high selectivity for methyl parathion in a wide linear range (2.45 nM-4.0 x 10(-8) M), low limit of detection value (1.49 nM) and high sensitivity (0.1847 mu A nM(-1)). Also, the developing non-enzymatic sensor exhibited good repeatability (RSD = 2.3% for 10 electrodes) and stability (85.30% for 30 days). Validation guidelines by HPLC and statistical analysis showed that the proposed voltammetric method were precise, accurate, sensitive, and can be used for the routine quality control of methyl parathion determination in juice samples.Öğe Synthesis and photovoltaic properties of novel ferrocene-substituted metallophthalocyanines(Royal Society of Chemistry, 2021) Özdemir, Mücahit; Köksoy, Baybars; Kuruca, Halid; Altindal, Ahmet; Durmus, Mahmut; Koyuncu, Sermet; Yalcin, Bahattin; Bulut, MustafaIn this paper, a series of new metallophthalocyanines, including ferrocene groups, were designed, synthesized and, characterized, and their photovoltaic properties were investigated as alternative electron-donor materials in bulk heterojunction (BHJ) solar cells. These products were synthesized by a Sonogashira cross-coupling reaction between tetraiodophthalocyanine and ethynyl ferrocene. The newly synthesized phthalocyanines (4-6) were characterized by FT-IR, UV-Vis, H-1 NMR, and MALDI-TOF spectroscopic methods and elemental analysis. The electrochemical characterizations were carried out by cyclic voltammetry as well as differential pulse voltammetry. Density functional theory calculations were realized to prove the charge separation between ferrocene as an electron-donor and the phthalocyanine ring as an acceptor. According to UV-Vis measurements, a 25 nm red-shift was observed for complex 4 compared with complexes 5 and 6. Finally, the photovoltaic performance of these compounds used as an electron-donor moiety in a BHJ device were investigated. A function of different blend ratios was tested by fabricating a series of BHJ devices with the architecture of FTO/PEDOT:PSS/4-6: PCBM blend/Ag with an identical thickness of the active layer. The results indicated that the photovoltaic conversion efficiency of BHJ devices exhibited a strong blend-ratio dependence. The maximum power conversion efficiency was obtained by 5-based devices, as 3.65%, with a blend ratio of 1.5 : 1.0 under standard AM 1.5 illumination.












