Browsing by Author "Zafer C."
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Item New perylene derivative dyes for dye-sensitized solar cells(2007) Zafer C.; Kus M.; Turkmen G.; Dincalp H.; Demic S.; Kuban B.; Teoman Y.; Icli S.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/cm2 short-circuit current and 1.61% overall conversion efficiency. © 2006.Item Optical and electrochemical properties of polyether derivatives of perylenediimides adsorbed on nanocrystalline metal oxide films(Elsevier, 2008) Kus M.; Hakli O.; Zafer C.; Varlikli C.; Demic S.; Özçelik S.; Icli S.We report optical and electrochemical properties of polyether derivatives of perylenediimides (PDIs) thin films formed in various materials (semiconductor, insulator, amorphous and self-assembly). Perylenediimides adsorbed on nanocrystalline TiO2 (NT) nanocrystalline alumina (NA), amorphous silicon (PS) and neat self-assemblied (SA) films were prepared and characterized based on spectroscopic, electrochemical, spectro-electrochemical techniques. The absorption and fluorescence spectra of PDIs in chloroform exhibit vibronic features. The fluorescence quantum yields (Φf) of PDIs with end amino substituents in chloroform solutions are over 0.95, while the quantum yield of triethoxyphenyl substituted PDI Φf value is 0.024 in solution. Optical spectroscopy proves that PDIs in metal oxide thin films form aggregated type complexes. An electrochromism, a color change from red to blue/violet, is observed on metal oxide films, that indicates existence of mono and dianion forms of PDIs. Reversibility of electrochemical reductions in NT film depends on the scanning rate. However, electrochromism in NA films is stable and reversibility is independent from scanning rate. Stable mono and diaionic species are formed on NA films. SA films show broad absorption peaks during the voltammetric scan. On the other hand, the first reduction onset potentials of PDIs are almost equal to the onset potential of capacitive current of TiO2 which lead to low efficiency in dye-sensitized solar cells. © 2008 Elsevier B.V. All rights reserved.Item Optical and photovoltaic properties of salicylaldimine-based azo ligands(2010) Dinçalp H.; Yavuz S.; Hakli O.; Zafer C.; Özsoy C.; Durucasu I.; Içli S.A series of azo dyes containing salicylaldimine-based ligands as side chains were prepared and characterized. Absorption and emission data in five solvents of different polarities were studied. Photoirradiation studies under an oxygen atmosphere in water showed that the Schiff base side chains enhanced the photo-oxidative stability of the azo chromophore. The electrochemical properties of the dyes were investigated by a cyclic voltammetry. The synthesized salicylaldimine-based azo dyes gave two irreversible oxidation potentials. Complexation behavior of synthesized compounds with titanium (IV) ions was illustrated by the change in their absorption spectra. These ligands are appropriate sensitizers for anchoring to the TiO2 surface chemically in dye-sensitized solar cell (DSSC) productions. Electron injection capacities to TiO2 and photovoltaic performance of the synthesized salicylaldimine-based azo dyes were tested with DSSC. © 2009 Elsevier B.V. All rights reserved.Item Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes(2011) Dinalp H.; Akar Z.; Zafer C.; Li S.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 TiO2 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 TiO2 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 TiO2 surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced. © 2011 Elsevier Ltd. All rights reserved.Item Highly soluble polyoxyethylene-perylene diimide: Optical, electrochemical and photovoltaic studies(2011) Birel O.H.; Zafer C.; Dincalp H.; Aydin B.; Can M.The synthesis and optical properties of a new dye molecule [PERKAT] were reported. The molecular structure of PERKAT was characterized by FT-IR and 1H 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.Item Synthesis and spectroscopic properties of a novel perylenediimide derivative(2011) Hakli-Birel O.; Dinçalp H.; Zafer C.; Demiç S.; Colladet K.; Vanderzande D.; Yürüm Y.; Içli S.A novel symmetric 3,4,9,10-perylenetetracarboxylic acid derivative (PDI1) dye based on thiophene donor group was synthesized and characterized by FT-IR and 1H NMR. Cyclic Voltammetry analysis is performed to determine the energy levels of the perylene derivative. Optical characteristics were determined by visible absorption and fluorescence emission spectra. Spectral behavior and fluorescence quantum yield of PDI1 have been measured in different solvents. The dye exhibits high fluorescence quantum yield (Φf: 0.94-0.99). But the quantum yield PDI1 is very low in the n-butanol solution (Φf: 0.12). The photophysical properties have important implications for use in a variety of electroactive and photovoltaic applications. A photovoltaic device was fabricated with PDI1 as transporting material. The conversion efficiency for DSSC sensitized by PDI1 is 0.0065%. PDI1 exhibits electrochromic behavior by switching between neutral (red) and oxidized (blue) states. Electron transfer capacity of PDI to the TiO2 was investigated by incorporation of dye as sensitizer in dye sensitized solar cell (DSSC). Soluble dye molecules are very important toprepare dye sensitized solar cell. Solubility was increased with thiophene group.Item Impact of the different electron-releasing subunits on the dye-sensitized solar cell performance of new triphenylamine-benzimidazole based molecules(Elsevier, 2015) Dinçalp H.; Saltan G.M.; Aykut D.; Zafer C.New triphenylamine-benzimidazole type small molecules with different electron-releasing groups were designed and synthesized to investigate their photovoltaic performances in dye sensitized solar cells (DSSCs). Their good visible absorptions covering the 400-535 nm in addition to suitable lowest unoccupied molecular orbital (LUMO) energy levels between -3.03 and -3.11 eV make good candidates them for DSSC devices. Fluorescence quenching studies of the dyes with pristine titania support the good electron injection to conduction band of TiO2. Time resolved measurements of the dyes in solutions indicate the occurence of charge generation during the excited state. One of the used dyes in DSSC devices, TPA5a, carrying a methoxy group in triphenylamine part of the structure, gave much higher power conversion efficiency (PCE) value of 4.31% as compared to the other derivatives. Device fabricated from TPA5a dye gives good external quantum efficiency (EQE) value above 70% at 460 nm. Also, electron impedance spectroscopy (EIS) analysis of the devices gives a good explanation of the understanding of the cell performances. © 2015 Elsevier B.V.Item Novel organic dyes based on phenyl-substituted benzimidazole for dye sensitized solar cells(Elsevier Ltd, 2015) Saltan G.M.; Dinçalp H.; Kiran M.; Zafer C.; Erbaş S.Ç.Two new sensitizers derived from benzimidazole core for dye-sensitized solar cell (DSSC) applications were designed and synthesized as D-π-A structures, in which two phenyl-substituted benzimidazole group, a phenyl ring and a cyanoacrylic acid were used as the electron donor, π-conjugated linkage and the electron acceptor, respectively. Effect of methoxy- and N,N-dimetylamino- moieties attached to the phenyl groups of benzimidazole were investigated by means of optical and photovoltaic measurements. The compounds exhibit broad absorption maximum at 387 nm with the tail extending up to 500 nm on TiO2-coated thin film. The longer wavelength absorption band around 360 nm and the much longer decay components could be attributed to the existence of charge transfer state of the dyes in solutions. DSSC device fabricated by using methoxy substituted dye (BI5a) as a sensitizer shows much better incident photon-to-current conversion efficiency (IPCE) of 64% giving cell efficiency of 2.68%. © 2015 Elsevier B.V. All rights reserved.Item Comparison of the Optoelectronic Performance of Neutral and Cationic Forms of Riboflavin(Springer New York LLC, 2017) Saltan G.M.; Kıymaz D.A.; Zafer C.; Dinçalp H.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 × 10−3 cm2/V∙s compared to its cationic derivative. © 2017, Springer Science+Business Media, LLC.Item Synthesis and photophysical characterization of isoindigo building blocks as molecular acceptors for organic photovoltaics(Elsevier B.V., 2018) Dinçalp H.; Saltan G.M.; Zafer C.; Mutlu A.Five isoindigo-based donor-acceptor-donor (D-A-D) type small molecules have been synthesized in order to investigate their intramolecular charge transfer characteristics. UV–vis absorption of these dyes exhibits a wide absorption band ranging from 300 to 650 nm with two distinct bands, giving the narrow bandgaps between 1.72 and 1.85 eV. Taking into account their HOMO-LUMO energy levels and bandgaps, isoindigo dyes have been used in the active layer of organic solar cell (OSC) devices. When these small molecule semiconductors were used as acceptors with the donor poly(3-hexylthiophene-2,5-diyl (P3HT) polymer in the inverted OSC devices, the highest power conversion efficiency (PCE) was obtained as 0.10% for pyrene-substituted isoindigo derivative. © 2018 Elsevier B.V.Item Indigo-Based Acceptor Type Small Molecules: Synthesis, Electrochemical and Optoelectronic Characterizations(Springer New York LLC, 2018) Saltan G.M.; Kıymaz D.A.; Zafer C.; Dinçalp H.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. © 2018, Springer Science+Business Media, LLC, part of Springer Nature.Item Bromo-substituted cibalackrot backbone, a versatile donor or acceptor main core for organic optoelectronic devices(Elsevier B.V., 2018) Dinçalp H.; Saltan G.M.; Zafer C.; Kıymaz D.A.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-III shows more prominent intramolecular charge transfer (ICT) complex than that of Ci-II dye. Electron mobilities of the order of 7.0 × 10−4 cm2/V and 3.1 × 10−4 cm2/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. © 2018 Elsevier B.V.Item Small biomolecule dopant retinals: Electron blocking layer in P3HT:PCBM type organic solar cells(Elsevier Ltd, 2018) Kırmacı E.; Dinçalp H.; Saltan G.M.; Kıran M.; Zafer C.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 and 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 photoisomerization rate constants of synthesized dyes were found to be about 3.3–16.4 × 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 × 10−4 and 7.1 × 10−4 cm2/V s for Ret-III and Ret-IV dyes, respectively. © 2017 Elsevier B.V.Item Optoelectronic performance comparison of new thiophene linked benzimidazole conjugates with diverse substitution patterns(Elsevier B.V., 2018) Saltan G.M.; Dinçalp H.; Kırmacı E.; Kıran M.; Zafer C.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. © 2017 Elsevier B.V.Item Double connector to TiO2 surface in small molecule triphenyl amine dyes for DSSC applications(Springer New York LLC, 2019) Özkan E.; Mutlu A.; Zafer C.; Dinçalp H.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 to ~ 550 nm with visible absorption maxima at 408–430 nm and optical band gaps of 2.44–2.47 eV. 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. © 2019, Springer Science+Business Media, LLC, part of Springer Nature.Item Enhanced performance of ultra-thin polyaniline supercapacitor via aniline blue-WS SAMs with rich nucleation site(IOP Publishing Ltd, 2021) Kiymaz D.; Kiymaz A.; Dincalp H.; Zafer C.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 ∼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. © 2021 IOP Publishing Ltd Printed in the UKItem Charge transport kinetics in flower like α-MnO2 nano-sheet and α-MnO2 nanowire based supercapacitors(Elsevier B.V., 2022) Kiymaz D.; Kiymaz A.; Tekoglu S.; Mayr F.; Dincalp H.; Zafer C.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 (α-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. © 2022 Elsevier B.V.Item Highly conjugated isoindigo and quinoxaline dyes as sunlight photosensitizers for onium salt-photoinitiated cationic polymerization of epoxy resins(John Wiley and Sons Ltd, 2022) Ercan B.T.; Gultekin S.S.; Yesil T.; Dincalp H.; Koyuncu S.; Yagci Y.; Zafer C.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. © 2021 Society of Industrial Chemistry. © 2021 Society of Industrial Chemistry.Item Conformational control of morphology for perylene diimide dimer as electron transporting material at perovskite surface(Elsevier B.V., 2023) Ötken A.A.; Saltan G.M.; Yeşil T.; Zafer C.; Dinçalp H.Synthesis of core-twisted perylene diimide (PDI) dimers attached with thiophene linkers (PDI-NHR-Th(1–4)) and their electron transporting ability at perovskite surface were studied. Synthesized dyes showed a high-lying lowest unoccupied molecular orbital (LUMO) energy levels between –3.68 and –3.71 eV, which were compatible with the conduction band of CH3NH3PbI2Br (–3.60 eV). Herein, we have investigated the role of the different substituted positions of PDI monomers to thiophene linkage from its (2,5)-, (3,4)-, (2,4)-, or (2,3)-positions in modulating the morphology of PDI dimer, aggregation behavior for charge transfer properties, optical shifts in ground and excited states, and recombination resistances at the interfaces of p-i-n devices. Conformational changes of PDI dimers attaching to different positions of thiophene linkers are found to affect not only photopysical dynamics of excited states of the dyes, but also charge transport kinetics at the perovskite interfaces, changing the photovoltaic performance. © 2023 Elsevier B.V.Item Perylene Diimide-Based Dimeric Electron Acceptors with Molecular Conformations for Perovskite Solar Cells(John Wiley and Sons Inc, 2024) Saltan G.M.; Yeşil T.; Ötken A.A.; Zafer C.; Dinçalp H.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. © 2024 Wiley-VCH GmbH.