MCBÜ Açıkerişim Sistemi :: Browsing by Author "Dinçalp H."

Browsing by Author "Dinçalp H."

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Photoinduced electron transfer-catalyzed processes of sulfoamino perylene diimide under concentrated sun light
(2006) Dinçalp H.; Içli S.
A new water-soluble perylene diimide derivative, N,N′-bis(12- sulfoaminododecyl)-3,4,9,10-perylenetetracarboxdiimide (SULFAPER), has been synthesized and characterized by visible, fluorescence, IR, 1H and 13C NMR, mass, CV and time resolved measurements. Its photophysical properties in aqueous and organic solutions have been described. The singlet energy levels of the synthesized compound have been found to be 57.8 kcal/mol and 59.2 kcal/mol in aqueous and methanol solution, respectively. The LUMO energy level of SULFAPER has been determined by solid state cyclic voltammetry, and found to be -3.60 eV. SULFAPER undergoes two electron reduction process (-0.64 V and -0.42 V) versus ferrocene. SULFAPER has an energy band gap of 2.56 eV. The absorption maximum of the synthesized compound gives bathochromic shift of 12 nm in water with respect to its visible spectrum in methanol solution. The fluorescence quantum yields of the compound are low both in water and methanol solution because of the aggregation effect. Time-resolved fluorescence measurements have showed that the fluorescence decay times of the SULFAPER are τ1 = 4.1 ns and τ2 = 0.8 ns in water, and τ1 = 4.0 ns and τ2 = 2.5 ns in methanol solutions. The aqueous solution of SULFAPER is stable under UV-VIS irradiation, but a slight loss of fluorescence emission (25%) has been detected at a rate of k p = 6.3 × 10-5 s-1 in methanol solution, which might be the result of either the quenching of fluorescence emission by reactive oxygen species, or by enhanced aggregation effect. SULFAPER-sensitized photooxidations of (E)-cinnamic acid and methyl acrylate have been found to give selective photoproduct formations under concentrated sun light in organic phase. (E)-cinnamic acid has been seen to favor photochemical E-Z isomerization and methyl acrylate has been seen to favor the formation of methyl 2-oxopropanoate. The quantum yield of (E)-cinnamic acid (ΦCA) under concentrated solar irradiation process has been calculated to be about 0.015, by the employment of an actinometry method developed by Erten and Icli. © 2005 Elsevier Ltd. All rights reserved.
New thiophene-based azo ligands containing azo methine group in the main chain for the determination of copper(II) ions
(2007) Dinçalp H.; Toker F.; Durucasu I.; Avcibaşi N.; Icli S.
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, 1H NMR, 13C 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 1011 and 1014 M-1 s-1, respectively. The free energies of photo-electron transfer process (ΔGET) 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 ∼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 (kc-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. © 2006 Elsevier Ltd. All rights reserved.
Preliminary tests of the radiopharmaceutical potential of N-(2,6-diisopropylphenyl)-N'-(4-pyridyl)-perylene-3,4,9,10-tetracarboxylic diimide radiolabeled with 131 I
(Springer Netherlands, 2007) Avcıbaşı U.; Dinçalp H.; Ünak T.; Yıldırım Y.; Avcibaşi N.; Duman Y.; Içli S.
Perylene diimide denvatives are one of the G-quadruplex DNA interactive agents which are thought to be useful in application of cancer treatment Starting from this consideration, N-(2,6-diisopropylphenyl)-N'-(4-pyridyl)- perylene-3,4,9,10-tetracarboxylic diimide (PYPER) was synthesized, radioiodinated with 131 I, and its radiopharmaceutical potentials were tested on a male Albino rabbit and male Albino Wistar rats. This compound was successfully radioiodinated with 131 I with a radioiodination yield of about 100%. Scintigraphic imaging with the radiiodinated compound ( 131 I-PYPER) was performed on a rabbit. Static images were obtained from posterior projection using a Diacan gamma camera at several time intervals. The scintigrams clearly showed that the radioiodinated compound was not quickly cleared from the metabolism, accumulating in the stomach over about 30 minutes. The clearance time of this compound was considerably longer than 5 hours. The results obtained in this study agreed with that of the biodistribution studies and indicated that 131 I-PYPER might be used as a scintigraphic agent for examining stomach diseases. © 2007 Springer Science+Business Media, Inc.
Metabolic comparison of radiolabeled aniline- and phenol-phthaleins with 131I
(2008) Avcibaşi U.; Avcibaşi N.; Ünak T.; Ünak P.; Müftüler F.Z.; Yildirim Y.; Dinçalp H.; Gümüşer F.G.; Dursun E.R.
The metabolic comparison of aniline- and phenol-phthaleins radiolabeled with 131I (131I-APH and 131I-PPH, respectively) has been investigated in this study. To compare the metabolic behavior of these phthaleins and their glucuronide conjugates radiolabeled with 131I, scintigraphic and biodistributional techniques were applied using male Albino rabbits. The results obtained have shown that these compounds were successfully radioiodinated with a radioiodination yield of about 100%. Maximum uptakes of 131I-APH and 131I-PPH, which were metabolized as N- and O-glucuronides, were observed within 2 h in the bladder and in the small intestine, respectively. In the case of verification of considerably up taking of these compounds also by tumors developed in the small intestine and in the bladder tissues, these results can be expected to be encouraging to test these compounds, which will be radiolabeled with other radioiodines such as 125I, 123I and 124I as imaging and therapeutic agents in nuclear medical applications. © 2008 Elsevier Inc. All rights reserved.
Fluorescent macromolecular perylene diimides containing pyrene or indole units in bay positions
(2010) Dinçalp H.; Kizilok S.; Içli S.
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, 1H and 13C NMR, MS, UV-Vis spectra and cyclic voltammetry. The λmax in 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. © 2009 Elsevier Ltd. All rights reserved.
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.
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.
Synthesis and G-quadruplex binding study of a novel full visible absorbing perylene diimide dye
(2012) Dinçalp H.; Kizilok Ş.; Birel O.H.; Içli S.
A novel perylene diimide dye containing glucopyranosyl groups in 1- and 7-positions of the perylene ring has been synthesized and characterized to obtain highly efficient and stable photosensitized material in photodynamic therapy. Solvatochromic studies on this dye in solvents of different polarities have indicated that absorption bands of the dye cover the whole visible spectrum in more polar organic solvents. It shows absorption bands localized at 350-500 nm and 600-850 nm in benzonitrile giving a green color. Also, the dye has a wide absorption region which covers the wavelength between 400 and 800 nm in more polar solvents by changing the dye concentration in the solvents. Singlet oxygen generation efficiency and G-quadruplex binding affinity of the dye have been tested. Theoretical calculations through semi-empirical methods have been performed and a detailed spectroscopic assignment of the molecule has been also presented. © 2012 Elsevier B.V.
Synthesis, characterization and optoelectronic properties of a new perylene diimide-benzimidazole type solar light harvesting dye
(Elsevier, 2014) Dinçalp H.; Çimen O.; Ameri T.; Brabec C.J.; Içli S.
A perylene diimide type small molecule (BI-PDI) has been synthesized through Suzuki coupling reaction between N,N′-bis(2,6-diisopropylphenyl)- 1,7-dibromoperylene-3,4,9,10-tetracarboxylic diimide and 2-(2-hydroxyphenyl)-7- phenyl-1H-benzimidazole-4-boronic acid. BI-PDI small molecule has showed an absorption band between 350 and 750 nm on thin films. HOMO and LUMO energy levels of BI-PDI dye have been calculated to be about -5.92 eV and -3.82 eV, respectively. Solution-processed bulk heterojunction (BHJ) solar cells have been constructed using BI-PDI as donor and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) as acceptor or poly(3-hexylthiophene) (P3HT) as donor and BI-PDI as acceptor. The external quantum efficiencies (EQE) of the devices cover the most of the visible region between 400 and 700 nm for both configurations. Photovoltaic performances of BI-PDI-based organic solar cells are limited by the aggregation tendency of PDI structure and poor hole/electron mobilities of the active layer. © 2014 Elsevier B.V. All rights reserved.
Improvement of intramolecular charge transfer within a donor-acceptor blend by doping novel synthesized benzothiadiazole small molecules in solid state
(Elsevier B.V., 2014) Dinçalp H.; Murat G.; Içli S.
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. © 2014 Elsevier B.V. All rights reserved.
Targeted singlet oxygen generation using different DNA-interacting perylene diimide type photosensitizers
(Springer New York LLC, 2014) Dinçalp H.; KIzIlok Ş.; Içli S.
Singlet oxygen quantum yields (ΦΔ) of different perylene diimides (PDIs) containing phenyl (PDI-Ph), pyrene (PDI-Pyr), and indole (PDI-In) units in bay positions of the ring were determined using 1,3-diphenylisobenzofuran (DPBF) method in toluene/methanol (99:1) system. Pyrene-substituted PDI were the most efficient singlet oxygen generator among the investigated photosensitizers with a quantum yield of Φ Δ=0.93 in toluene/methanol. Additionally, their binding affinities to G-quadruplex DNA structure were investigated by steady-state measurements. There were marked red shifts of absorbance bands for PDI-Pyr/DNA strand complexes with respect to the absorption maxima of DNA-free solution of PDI-Pyr in phosphate buffer at pH 6. © 2014 Springer Science+Business Media New York.
Functionalized bay-substituted perylene diimide additives for inverted organic photovoltaic devices based on P3HT/PCBM
(National Institute of Optoelectronics, 2015) Dinçalp H.; Çmen O.; Murat Saltan G.; Çl S.
The photovoltaic performances of inverted organic solar cells including P3HT:PCBM active layer with perylene diimides (PDIs) substituted with different subunits at bay positions of perylene ring were investigated. The improvement of photoluminescence intensity for P3HT:PCBM blend was achieved by the increase of PDI1 additive amount from 6.6 to 10 wt%. In P3HT:PDI1:PCBM ternary blend, preliminary results obtained from cell measurements indicated that PDI1 dopant has improved the cell efficiency by 38% compared to the control cell. Carrier mobility studies revealed that electron or hole mobility capacities of the perylene additives in ternary blends gave a more detailed explanation for efficiencies both binary and ternary systems.
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.
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.
Pyrene bisiminopyridine ligand and its zinc complex
(Taylor and Francis Inc., 2016) Ayadi A.; Branzea D.; Dinçalp H.; Zouari N.; El-Ghayoury A.
The synthesis of a pyrene bisiminopyridine ligand L was successfully accomplished by condensation between 1-aminopyrene and 2,6-pyridinecarboxaldehyde. The complexation of L with zinc triflate afforded a neutral metal complex formulated as [Zn(H2O)LCF3SO3)2].2Et2O. In the complex, the ligand is coordinated to zinc(II) through its three nitrogen atoms which form a distorted octahedral environment together with three oxygen atoms, two from the triflate anions and one from aqua ligand. Both compounds have been characterized using NMR, elemental analysis, mass spectrometry, electronic absorption (UV-Vis) and infrared. Luminescence properties of these compounds show an emission maxima at 412 nm, indicating a pyrene monomer emission. © 2016 Taylor & Francis Group, LLC.
Coordination entities of a pyrene-based iminopyridine ligand: Structural and photophysical properties
(Elsevier Ltd, 2017) Ayadi A.; Branzea D.G.; Allain M.; Canevet D.; Dinçalp H.; El-Ghayoury A.
A pyrene-based iminopyridine ligand L has been prepared and displays the absorption and emission properties expected for pyrene-based derivatives in solution. Ligand L, as well as two neutral and one monocationic coordination entities, respectively formulated as [ZnLCl2] 1, [ReLCl(CO)3] 3 and [CuL2](BF4) 2, have been crystallized and analyzed by single crystal X-ray diffraction analysis. The corresponding crystal structures indicate the formation of supramolecular architectures generated by offset π⋯π stacking between pyrene fragments and strong C–H⋯π interactions in coordination entity 1. For the cationic coordination entity 2, the crystal packing reveals the presence of C–H⋯F and C–H⋯π interactions and numerous C–H⋯π contacts interconnecting the molecules into a 3D network. As for coordination entity 3, hydrogen bonding and π⋯π stacking link the molecules in a three dimensional manner. Zinc(II) and copper(I) coordination entities have also been studied through isothermal titration calorimetry, which indicate a strong binding and a different stoichiometry for both coordination entities. Photophysical studies of the ligand and corresponding coordination entities show a monomer type pyrene emission and a higher fluorescence quantum yield for the zinc coordination entity 1 as compared with copper 2 and rhenium 3 coordination entities. © 2017 Elsevier Ltd
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.
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.
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.
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.

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