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Bromo-substituted cibalackrot backbone, a versatile donor or acceptor main core for organic optoelectronic devices
(Elsevier Science Bv, 2018) Dincalp, Haluk; Saltan, Gozde Murat; Zafer, Ceylan; Kiymaz, Deniz Aykut
Cibalackrot (Ci-I), one of the latest highly conjugated compound possessing bis-lactam structure, was investigated with respect to their brominated derivatives in order to determine their suitable substitution points for the syntheses of new class of small molecules for optoelectronic devices. 7,14-Bis(4-bromophenyl) (Ci-II) and 3,10-dibromo (Ci-III) derivatives of cibalackrot possess moderately narrow band gaps of 2.15 and 2.09 eV, respectively. Notably, Ci-III dye exhibits more red-shifted ultraviolet -visible (UV vis) absorption and fluorescence emission spectra as compared to that of Ci-II dye because Ci-Ill shows more prominent intramolecular charge transfer (ICT) complex than that of Ci-II dye. Electron mobilities of the order of 7.0 x 10(-4) cm(2)/V and 3.1 x 10(-4) cm(2)/V were measured using Ci-II and Ci-III as active layer, respectively. Charge transfer properties of the molecules were investigated in bulk heterojunction device configuration wherein Ci-III showed p-type behavior against n-type PCBM in photovoltaic device. Photovoltaic performance of Ci-III dye which was used as donor component is 20 times higher than that of the device in which this dye was used as acceptor. (C) 2018 Elsevier B.V. All rights reserved.
Charge transport kinetics in flower like alpha-MnO2 nano-sheet and alpha-MnO2 nanowire based supercapacitors
(Elsevier Science Sa, 2022) Kiymaz, Deniz; Kiymaz, Aykut; Tekoglu, Serpil; Mayr, Felix; Dincalp, Haluk; Zafer, Ceylan
In a supercapacitor, determining the cells' internal dynamics and limiting factors on the efficiency is essential for device designs. In this context, electrochemical impedance spectroscopy is a powerful tool in investigating device kinetics. This study explained the performance improvement in nanostructured MnO2 electrodes from a diffusion perspective. Firstly, we reported morphological features of flower-like nanosheet MnO2 and nanowire MnO2 with identical crystal structure (alpha-MnO2 phase) and capacitance-voltage properties. Then, the factors limiting the bias voltage-dependent capacitance efficiency were explained via electrochemical impedance spectroscopy by setting up a three-electrode system. Both resistance and capacitance vs. frequency plots provided important information on ion diffusion and charge transfer mechanisms.
Comparison of the Optoelectronic Performance of Neutral and Cationic Forms of Riboflavin
(Springer/Plenum Publishers, 2017) Saltan, Gozde Murat; Kiymaz, Deniz Aykut; Zafer, Ceylan; Dincalp, Haluk
The riboflavin dye 2,3,4,5-tetra-O-acetyl-1-[3-(6-bromohexyl)-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl]-1-deoxypentitol and its pyridinium salt were synthesized, and studied by absorption and fluorescence spectroscopy in solutions and on thin film states. The first absorption band of riboflavin-pyridinium salt derivative is red-shifted by 10 nm compared to neutral one on film. Cationic riboflavin derivative shows significant wavelength changes on its fluorescence emission spectrum in the excited state depending on the solvent polarity and the electronic environment. The fluorescence quantum yields of cationic riboflavin gave much higher values as compared to that of its neutral form. The fluorescence lifetimes were found to be in the range of 5.5-6.6 ns with mono - exponential behavior. These dyes possess low-lying HOMO energy levels which are suitable to be able to inject holes to donor polymers so that they can be used as acceptor component in the active layer of bulk heterojunction solar cells (BHJ-SCs). Photovoltaic responses are reported for P3HT:riboflavin active layer wherein the synthesized dyes are used as acceptor component. Also, neutral riboflavin shows greater electron mobility value of 1.3 x 10(-3) cm(2)/Va (TM) s compared to its cationic derivative.
Double connector to TiO2 surface in small molecule triphenyl amine dyes for DSSC applications
(Springer, 2019) Ozkan, Eren; Mutlu, Adem; Zafer, Ceylan; Dincalp, Haluk
Two novel dyes 3a and 3b named triphenylamine groups containing donor-acceptor structural units have been explored to be used in dye sensitized solar cells as organic sensitizers. The absorption bands of the dyes were extended up to550nm with visible absorption maxima at 408-430nm and optical band gaps of 2.44-2.47eV. Compared to the methoxyphenyl-substituted dye, the introduction of triisopropylphenyl group instead of that increased fluorescence quantum yields and exhibited red-shift emission in chloroform. We have investigated the photovoltaic properties of DSSCs based on these metal free organic dyes. It has been found that the power conversion efficiency of DSSCs sensitized with methoxyphenyl based triphenylamine dye is higher than that for sensitized with triisopropylphenyl derivative.
Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes
(Elsevier Sci Ltd, 2011) Dincalp, Haluk; Askar, Zuhal; Zafer, Ceylan; Icli, Siddik
Three near-infrared (NIR) absorbing unsymmetrical perylene diimide D A D type dyes containing 6-undecanoxy as donor group were utilized in dye-sensitized nanocrystalline TiO(2) solar cells. Structure of the acceptor side of the molecules were improved by adding 4-[2-methyl-5-(cyanoacrylic acid)-3-thienyl]-phenyl (V), 3-carboxy-2-pyridil (VI) and 3-carboxy-2-pyrazyl (VII) moieties attached to one of the N-side of the dye. The relationship between the molecular structure of the acceptor sites of the dyes and the photovoltaic performances were discussed. Electrochemical measurements indicated that band gaps of the dyes were energetically favorable for electron injection from the excited state of the dyes to the conduction band of TiO(2) nanoparticles. However, three dyes gave lower conversion efficiency on DSSC applications. Strong electron-withdrawing nature of perylene core might not permit to transfer the photo-generated electrons to the carboxyl groups anchoring to TiO(2) surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced. (C) 2011 Elsevier Ltd. All rights reserved.
Enhanced performance of ultra-thin polyaniline supercapacitor via aniline blue-WS SAMs with rich nucleation site
(Iop Publishing Ltd, 2021) Kiymaz, Deniz; Kiymaz, Aykut; Dincalp, Haluk; Zafer, Ceylan
We report the ultrathin supercapacitor's superior performance via the vertically aligned one-dimensional polyaniline structure (1D PANI) growth on the fluorine-doped tin oxide (FTO) substrate. FTO electrodes were treated by the molecular-self assembly, and the effects of different self assembled monolayers (SAMs) on both the evolution of PANI and electrochemical performance were examined. We obtained 809.09 F g(-1) specific capacitance from similar to 120 nm thick PANI (at 20 mV s(-1) scan rate of cyclic voltammetry) via aniline blue water soluble SAMs modification. The supercapacitor's internal dynamics were clarified by a new equivalent circuit model developed from the Graham model. Through the new model, accurate information about double-layer capacitance, percolation capacitance, and bulk capacitance, which composes the electrode's capacitive performance, could be obtained. This work provided novel knowledge to develop PANI deposition and hence to achieve greater capacitances.
Fluorescent macromolecular perylene diimides containing pyrene or indole units in bay positions
(Elsevier Sci Ltd, 2010) Dincalp, Haluk; Kizilok, Sevki; Icli, Siddik
Novel, symmetric and unsymmetric perylene diimide dyes with pyrene or indole units in the bay positions of the perylene ring were synthesized and characterized using FT-IR, (1)H and (13)C NMR, MS, UV-Vis spectra and cyclic voltammetry. The lambda(max) different solvents were in the range 526-585 nm and emission wavelengths of the dyes exhibited positive solvatochromism with increasing solvent polarity. Long wavelength emissions >750 nm of dyes with pyrene units displayed charge-separated state of perylene-pyrene system. Dyes with pyrene or indole units showed greater photostability in toluene than dyes which did not contain these bulky substituents. Incorporating electron-donating indole substituents lowered the band gap energies and, therefore, the HOMO energy levels were increased. The energy density and shape of the molecular orbitals were calculated theoretically. (C) 2009 Elsevier Ltd. All rights reserved.
Highly conjugated isoindigo and quinoxaline dyes as sunlight photosensitizers for onium salt-photoinitiated cationic polymerization of epoxy resins
(Wiley, 2022) Ercan, Bahar T.; Gultekin, Sirin S.; Yesil, Tamer; Dincalp, Haluk; Koyuncu, Sermet; Yagci, Yusuf; Zafer, Ceylan
In this study, photoinitiated cationic polymerization of epoxy resins by photoinduced electron transfer reactions using four new chromophoric dyes, namely (3E)-1,1 '-bis(2-ethylhexyl)-6,6 '-dipyren-1-yl-3,3 '-biindole-2,2 '(1H,1 ' H)-dione (ISOIV), (3 ' E)-1,1 '''-diethyl-1 ',1 ''-bis(2-ethylhexyl)-1H,1 ''' H-5,6 ':3 ',3 '':6 '',5 '''-quaterindole-2 ',2 ''(1 ' H,1 '' H)-dione (ISOV), (3E)-6,6 '-bis(9-ethyl-9H-carbazole-3-yl)-1-[(2R)-2-ethylhexyl]-1 '-[(2S)-2-ethylhexyl]-3,3 '-biindole-2,2 '(1H,1 ' H)-dione (ISOVIII) and 3,3 '-(6-bromokinoksalin-2,3-diyl)bis(9-ethyl-9H-carbazole) (TPDC6), and diphenyliodonium hexafluorophosphate (Ph2I+PF6-; DPI) under sunlight is reported. Upon irradiation, photoexcited dye forms an exciplex with DPI. Electron transfer reactions within the exciplex result in the formation of ionic species capable of initiating ring-opening polymerization of an epoxy resin. It is shown that among the investigated dyes, ISOVIII and TPDC6 exhibited higher initiation efficiency in accordance with their stronger electron-donating nature due to the presence of carbazole groups. (c) 2021 Society of Industrial Chemistry.
Highly Soluble Polyoxyethylene-Perylene diimide: Optical, Electrochemical and Photovoltaic Studies
(Chem Soc Pakistan, 2011) Birel, O. Hakli; Zafer, Ceylan; Dincalp, Haluk; Aydin, Banu; Can, Mustafa
The synthesis and optical properties of a new dye molecule [PERKAT] were reported. The molecular structure of PERKAT was characterized by FT-IR and (1)H NMR. Optical properties of PERKAT were investigated by UV-Vis absorption, fluorescence spectroscopy. The effect of the solvent polarity on the spectral characteristics has been investigated in five common organic solvents of different polarity. PERKAT is highly soluble in common organic solvents such as chloroform, dichloromethane due to the polyoxyethylene chains. The fluorescence quantum yields of PERKAT in all solvents is very low (10(-2) -10(-3)). Cyclic Voltammetry (CV) analysis was performed to determine the HOMO and LUMO energy levels of the PERKAT. PERKAT was used as electron acceptor material in organic solar cell.
Improvement of intramolecular charge transfer within a donor-acceptor blend by doping novel synthesized benzothiadiazole small molecules in solid state
(Elsevier, 2014) Dincalp, Haluk; Murat, Gozde; Icli, Siddik
Three electron-deficient small molecules based on 2,1,3-benzothiadiazole (BTD) units namely, 4,7-bis (3-methoxyphenyl)-2,1,3-benzothiadiazole (BT1), (3-{7-[3-(dimethylamino)phenyl]-2,1,3-benzothiadiazole-4-yl}phenyl)dimethylamine (BT2) and 3,3'-(2,1,3-benzothiadiazole-4,7-dyl)dianiline (BT3) were synthesized and their photophysical properties were investigated systematically to understand their potential usage in ternary organic solar cells (OSCs) as additive material to enhance the cell efficiency. All these molecules show broad absorption bands in 350-750 nm on glass substrate and their optical band gaps were calculated to be around 2.50-2.80 eV. BTD fluorescence dynamics were measured in polymer:BT1:fullerene blends with varying emission wavelengths of active layer. Fluorescence emission and time resolved measurements indicated photoinduced energy shift from BT1 dye to fullerene and also from polymer to BT1 dye upon excitation of the active layer. (C) 2014 Elsevier B.V. All rights reserved.
Indigo-Based Acceptor Type Small Molecules: Synthesis, Electrochemical and Optoelectronic Characterizations
(Springer/Plenum Publishers, 2018) Saltan, Gozde Murat; Kiymaz, Deniz Aykut; Zafer, Ceylan; Dincalp, Haluk
In this paper, we report design and synthesis of novel low bandgap small molecules, indigo-benzimidazole (Tyr-3) and indigo-schiff base (Tyr-4) type acceptors. In these structures, tert-butoxycarbonyl (t-BOC) group has been attached to indigo nitrogen atom in order to increase the solubility. UV-vis absorption spectra of Tyr-3 and Tyr-4 dyes exhibit wide absorption bands ranging from 350 to 600 nm, indicating the relatively low bandgap giving around 2.07 eV for each. Excitation of both Tyr-3 and Tyr-4 dyes at 485 nm displays characteristic emission features of indigo moiety and also intramolecular charge transfer complex (ICT) related with their subunits. Besides increasing fluorescence quantum yields as compared to model compound, biexponential decay times for fluorescence life times were also obtained for Tyr-3 and Tyr-4 dyes. Their appropriate energy levels along with low HOMO levels are desired for light harvesting acceptors for organic solar cells when blended with poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4,7-di-2-thienyl-2',1',3'-benzothiadiazole] (PCDTBT) as donor polymer. Photovoltaic behavior of the synthesized dyes were examined in bulk heterojunction concept and achieved photovoltaic conversion efficiencies were discussed.
New perylene derivative dyes for dye-sensitized solar cells
(Elsevier Science Bv, 2007) Zafer, Ceylan; Kus, Mahmut; Turkmen, Gulsah; Dincalp, Haluk; Demic, Serafettin; Kuban, Baha; Teoman, Yildirim; Icli, Siddik
We have studied the influence of the spacer alkyl chain length of perylenemonoimide (PMI) dyes on the device performance in dye-sensitized solar cells (DSSCs). We observed that the dyes with longer and brunched alkyl chains exhibit higher efficiencies in DSSCs. In line with these statements we now report the highest efficiency obtained under standard conditions for a perylene imide derivative with PMI-DA1 that performs 300 mV open circuit voltage, 9.79 mA/cm(2) short-circuit current and 1.61% overall conversion efficiency. (c) 2006 Published by Elsevier B.V.
New thiophene-based azo ligands containing azo methine group in the main chain for the determination of copper(II) ions
(Elsevier Sci Ltd, 2007) Dincalp, Haluk; Toker, Fatih; Dutucasu, Inci; Avcibasi, Nesibe; Icli, Siddik
New kind of azo chromophores containing thiophene moiety and salicyaldimine-based ligand as side chains have been synthesized by a sequential process for optical sensing of Cu2+ metal ions in organic solution. Compounds have been characterized by IR and UV-vis spectrophotometer, H-1 NMR, C-13 NMR, MS, TGA and CV instruments. Spectral characteristics of the synthesized compounds have been investigated in five organic solvents of different polarity. Polarizibility effects of the solvents on the spectral characteristics and the dipole moments in the excited state are estimated. The fluorescence quantum yields of the synthesized compounds have been calculated to be in the range of 0.0035-0.0095 in solvents of different polarity. The fluorescence emission quenching experiments between the synthesized compounds and electron donor (pyrene, anthracene), electron acceptor (Co2+) compounds give the bimolecular quenching rate constants of 10(11) and 10(14) M-1 s(-1), respectively. The free energies of photo-electron transfer process (Delta G(ET)) between the azo dyes and the quenchers have been found to be about -19 kcal/mol. Cyclic voltammetry studies indicate that synthesized azo ligands undergo two- or three-reversible reduction potentials (versus ferrocene) and give LUMO energy value of -3.07 eV which is lower than that of TiO2 conduction band and has a band gap value of similar to 2.5 eV. These results may point that synthesized azo, dyes could be used as hole conducting materials in solid DSSC (Dye Sensitized Solar Cell) devices. Thermal decomposition behavior of the azo dyes gives more information about the structure of the studied materials. The photoisomerization behavior of the synthesized compounds has been investigated in ethyl acetate under Xe lamp irradiation in the fluorescence spectrophotometer for 1 h. Photoisomerization rate constants of cis-trans orientation (k(c-t)) have been found to be about 10(-5) s(-1). The complexation process of synthesized thienylidene azo dyes gives subtle changes in their absorption spectra. (C) 2006 Elsevier Ltd. All rights reserved.
Optoelectronic performance comparison of new thiophene linked benzimidazole conjugates with diverse substitution patterns
(Pergamon-Elsevier Science Ltd, 2018) Saltan, Gozde Murat; Dincalp, Haluk; Kirmaci, Eser; Kiran, Merve; Zafer, Ceylan
In an approach to develop efficient organic optoelectronic devices to be used in light-driven systems, a series of three thiophene linked benzimidazole conjugates were synthesized and characterized. The combination of two thiophene rings to a benzimidazole core decorated with different functional groups (such as -OCH3, N(CH3)(2), CF3) resulted in donor-acceptor type molecular scaffold. The effect of the electronic behavior of the substituents on the optical, electrochemical, morphological and electron/hole transporting properties of the dyes were systematically investigated. DTBI2 dye exhibited distinct absorption properties among the other studied dyes because N,N-dimethylamino group initiated intramolecular charge transfer (ICT) process in the studied solvents. In solid state, the dyes exhibit peaks extending up to 600 nm. Depending on the solvent polarities, dyes show significant wavelength changes on their fluorescence emission spectra in the excited states. Morphological parameters of the thin films spin-coated from CHCl3 solution were investigated by using AFM instrument; furthermore photovoltaic responses are reported, even though photovoltaic performances of the fabricated solar cells with different configurations are quite low. (C) 2017 Elsevier B.V. All rights reserved.
Perylene Diimide-Based Dimeric Electron Acceptors with Molecular Conformations for Perovskite Solar Cells
(Wiley-V C H Verlag Gmbh, 2024) Saltan, Goezde Murat; Yesil, Tamer; Otken, Aysun Albayrak; Zafer, Ceylan; Dincalp, Haluk
This paper reports five novel PDI dimer type electron transport materials (ETMs) employing o-indoloquinoxaline (o-Iq), m-indoloquinoxaline (m-Iq), and cibalackrot (Ci) groups as the core building blocks and presents the twisted structures of PDI dimers coded as PDI-NHR-o-Iq, PDI-o-Iq, PDI-NHR-m-Iq, PDI-m-Iq and PDI-NHR-Ci dyes (see Scheme 1 and 2). We have systematically compared their photophysical, electrochemical, and optoelectronic properties with respect to the reference dye (2PDI-NHR), which is directly connected of two PDI planes. Their calculated HOMO-LUMO energy levels are sufficient for charge transfer to the perovskite material so that structure-photovoltaic performance relationship of synthesized ETM dyes can be evaluated. When the binding position of indoloquinoxaline group between PDI rings are changed from o- to m- positions, most of the photophysical and electrochemical properties of PDI dimer are dramatically changed, finally improving the photovoltaic performances. Indoloquinoxaline and cibalackrot subunits covalently attached to perylene diimide dimers decorated with long-alkyl chains used as ETM are coated on the MAPbI2Br perovskite surface to manufacture solar cells. Attaching groups improve the charge transfer capability of the material depending on their molecular conformation, which plays important role in adjusting the energy level between the perovskite material and the ETL. image
Small biomolecule dopant retinals: Electron blocking layer in P3HT:PCBM type organic solar cells
(Elsevier Science Sa, 2018) Kirmaci, Eser; Dincalp, Haluk; Saltan, Gozde Murat; Kiran, Merve; Zafer, Ceylan
We present a comparative study of the photophysics and electron/hole properties of all-trans retinal-benzimidazole type molecules decorated with different electronic moieties (such as -OCH3, -N(CH3)(2), -F, -CF3) in organic photovoltaic (OPV) devices in solution end on solid thin films. Steady-state spectra of synthesized dyes give large Stokes shifts (6887-13152 cm(-1)) in studied solvents. Decay times of these dyes were found to be substituent dependent giving a bi-exponential decay for fluorine containing retinals. Trans to cis photo-isomerization rate constants of synthesized dyes were found to be about 3.3-16.4 x 10(-6) s(-1). Using a cyclic voltammetry measurements, HOMO and LUMO energy levels of fluorine-substituted dyes shift to lower values as compared to that of unfluorinated derivatives. We compared unusual electron blocking behavior of methoxy- and N,N-dimethylamino-substituted derivatives (Ret-I and Ret-II, respectively) in bulk heterojunction solar cells (BHJ-SCs) incorporating an active layer of P3HT:PCBM doped with Ret derivatives at various weight ratios. Hole mobility values for fluorine containing retinals were found to be about 1.0 x 10(-4) and 7.1 x 10(-4) cm(2)/V s for Retail and Ret-IV dyes, respectively.
Spectral properties and G-quadruplex DNA binding selectivities of a series of unsymmetrical perylene diimides
(Elsevier Science Sa, 2007) Dincalp, Haluk; Avcibasi, Nesibe; Icli, Siddik
A series of new unsymmetrical perylene diimides have been synthesized to investigate their binding selectivities to G-quadruplex DNA structure, a unique four-stranded DNA motif, which is significant to the regulation of telomerase activity. The structures of the perylene diimides have been characterized by IR spectrophotometer, H-1 NMR, C-13 NMR, MS, TGA and time-resolved instruments. Spectrochemical behaviors have been investigated by visible absorption and fluorescence emission spectra. The spectral characterization of the compounds has been investigated in five common organic solvents of different polarity and in water (in 170 mM phosphate buffer at pH 6). Marked red shifts of absorbance and fluorescence emission bands of the compounds in aqueous solution are compared with the other organic solutions. The fluorescence quantum yields are determined low in more polar solvents and also calculated to be about less than about 0.05 in aqueous solution because of the aggregation effects. Photodegradation rate constants (k(p)) of the synthesized compounds have been compared under xenon lamp irradiation in acetonitrile solution. Binding abilities of the synthesized perylene diimides to different form of DNA strands have been investigated by visible absorption and fluorescence spectroscopy in the phosphate buffer solutions. Also, pH-dependent aggregation and G-quadruplex DNA binding selectivity of these ligands have been compared. Among these ligands, N-(2,6-diisopropylphenyl)-N'-(4-pyridyl)-perylene-3,4,9,10-tetracarboxylic diimide (PYPER) has been found to be the most selective interactive ligand for G-quadruplex formed in the G4'-DNA structure. PYPER has shown a significant selectivity to G4'-DNA which is comprised of d(TTAGGG) repeats, known as human telomeres, in the phosphate buffer at pH 6. The absorption maximum of the PYPER/G4'-DNA complex has given bathochromic shift of 7 nm with respect to the absorption maximum of DNA-free solution of PYPER in phosphate buffer at pH 6. Fluorescence quenching experiments between PYPER and G4'-DNA show that PYPER demonstrates about a 9.3-fold selectivity for binding to G4'-DNA versus ds-DNA base pairs with the bimolecular rate constant of 0.95 x 10(12) M-1 s(-1). (c) 2006 Elsevier B.V. All rights reserved.
Studies on UV-vis and fluorescence changements in Co2+ and Cu2+ recognition by a new benzimidazole-benzothiadiazole derivative
(Elsevier Science Sa, 2015) Cimen, Oguzhan; Dincalp, Haluk; Varlikli, Canan
A novel fluorescent sensor (BI-T) was synthesized by the coupling reaction of 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid with 4,7-dibromo-2,1,3-benzothiadiazole via Pd-catalysed Suzuki reaction. Its photophysical properties were investigated systematically in different solvents to analyze its potential usage in the fluorescence detection for transition metal ions such as Co2+ and Cu2+ in solutions. In benzonitrile solution, new absorption bands for complex structure of BI-T at 470 nm and 580 nm were appeared in the presence of Co2+ ions with respect to the uncomplexed form of the sensor absorption. BI-T sensor is usable for both Co2+ and Cu2+ sensation through "on-off" fluorescence change in benzonitrile. In ethanol solution, BI-T shows similar optical performances to detect Co2+ and Cu2+ ions. BI-T detects trace amount of transition metals in ethanol with estimated limit of detection around 4.1 x 10(-7) M and 5.5 x 10(-7) M for Co2+ and Cu2+ ions, respectively. Possible formation of metal-to-ligand charge transfer (MLCT) state during the titration with Co2+ ion is supported by the detection of long-lived species in the excited state. (C) 2014 Elsevier B.V. All rights reserved.
Studies on UV-vis and fluorescence changements in Co2+ and Cu2+ recognition by a new benzimidazole-benzothiadiazole derivative
(Elsevier Science Sa, 2015) Cimen, Oguzhan; Dincalp, Haluk; Varlikli, Canan
A novel fluorescent sensor (BI-T) was synthesized by the coupling reaction of 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid with 4,7-dibromo-2,1,3-benzothiadiazole via Pd-catalysed Suzuki reaction. Its photophysical properties were investigated systematically in different solvents to analyze its potential usage in the fluorescence detection for transition metal ions such as Co2+ and Cu2+ in solutions. In benzonitrile solution, new absorption bands for complex structure of BI-T at 470 nm and 580 nm were appeared in the presence of Co2+ ions with respect to the uncomplexed form of the sensor absorption. BI-T sensor is usable for both Co2+ and Cu2+ sensation through "on-off" fluorescence change in benzonitrile. In ethanol solution, BI-T shows similar optical performances to detect Co2+ and Cu2+ ions. BI-T detects trace amount of transition metals in ethanol with estimated limit of detection around 4.1 x 10(-7) M and 5.5 x 10(-7) M for Co2+ and Cu2+ ions, respectively. Possible formation of metal-to-ligand charge transfer (MLCT) state during the titration with Co2+ ion is supported by the detection of long-lived species in the excited state. (C) 2014 Elsevier B.V. All rights reserved.
Studies on UV-vis and fluorescence changements in Co2+ and Cu2+ recognition by a new benzimidazole-benzothiadiazole derivative
(Elsevier Science Sa, 2015) Cimen, Oguzhan; Dincalp, Haluk; Varlikli, Canan
A novel fluorescent sensor (BI-T) was synthesized by the coupling reaction of 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid with 4,7-dibromo-2,1,3-benzothiadiazole via Pd-catalysed Suzuki reaction. Its photophysical properties were investigated systematically in different solvents to analyze its potential usage in the fluorescence detection for transition metal ions such as Co2+ and Cu2+ in solutions. In benzonitrile solution, new absorption bands for complex structure of BI-T at 470 nm and 580 nm were appeared in the presence of Co2+ ions with respect to the uncomplexed form of the sensor absorption. BI-T sensor is usable for both Co2+ and Cu2+ sensation through "on-off" fluorescence change in benzonitrile. In ethanol solution, BI-T shows similar optical performances to detect Co2+ and Cu2+ ions. BI-T detects trace amount of transition metals in ethanol with estimated limit of detection around 4.1 x 10(-7) M and 5.5 x 10(-7) M for Co2+ and Cu2+ ions, respectively. Possible formation of metal-to-ligand charge transfer (MLCT) state during the titration with Co2+ ion is supported by the detection of long-lived species in the excited state. (C) 2014 Elsevier B.V. All rights reserved.

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