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Article Citation - WoS: 5Citation - Scopus: 6An Electrochromic Polymer Based on Cyclopenta[2,1-B;3,4 Effect of a Single Atom Alteration on the Electrochemical and Optical Properties of the Polymer Backbone(Elsevier Science Sa, 2020) Tutuncu, Esra; Varlik, Bengisu; Kesimal, Busra; Cihaner, Atilla; Ozkut, Merve IcliAn electrochromic polymer, namely "poly(2,6-(3,3-didecyl-3,4-dihydro-2H-thieno [3,4-b] [1,4]dioxepin-6-yl)-4,4-dioctyl-4H-cyclopenta[2,1-b;3,4-b']dithiophene)" (P1), was electrochemically synthesized successfully, and its electrochemical and optical properties were investigated. The band gap of the polymer P1 was calculated as 1.77 eV with -5.45 eV Highest Occupied Molecular Orbital (HOMO) and -3.68 eV Lowest Unoccupied Molecular Orbital (LUMO) energy levels. The polymer P1 is bluish purple when neutralized and highly transparent greenish purple when oxidized. This color change was observed around 1.4 s between its redox states and optical contrast ratio was found to be as 49 % and 53 % with 234 cm(2)/C and 239 cm(2)/C coloration efficiencies at 590 nm and 634 nm, respectively. Moreover, the properties of this polymer were compared to its analogues and also during this comparison the effect of alteration of a single atom in the pendant unit was tried to be understood.Article Citation - WoS: 18Citation - Scopus: 19Effect of Furan, Thiophene and Selenophene Donor Groups on Benzoselenadiazole Based Donor-Acceptor Systems(Elsevier Science Sa, 2016) Karabay, Lutfiye Canan; Karabay, Bads; Karakoy, Merve Serife; Cihaner, AtillaA series of the monomers called 4,7-di(furan-2-yl)benzo[c][1,2,5]selenadiazole (OSeO), 4,7-di(thiophen-2-yl)benzo[c]11,2,5]selenadiazole (SSeS) and 4,7-di(selenophen-2-yl)benzo[c][1,2,5]selenadiazole (SeSeSe) was synthesized via a donor-acceptor-donor (D-A-D) approach. Benzoselenadiazole was used as an acceptor unit and furan, thiophene and selenophene were used as donor units. The effects of chalcogen atoms (0, S, and Se) in furan, thiophene and selenophene were investigated systematically on the properties of the monomers and their corresponding polymers (POSeO, PSSeS and PSeSeSe, respectively), which were polymerized electrochemically via potentiodynamic or potentiostatic methods. The monomers OSeO, SSeS and SeSeSe exhibited low oxidation potentials of 1.15, 1.25 and 1.19 V vs. Ag/AgCl, respectively. Intramolecular charge transfer interaction between donor and acceptor units was demonstrated from the emission spectra of the monomers. Also, the optical studies showed that the ambipolar and electrochromic polymers POSeO, PSSeS and PSeSeSe have low band gaps of 1.57, 1.47 and 1.45 eV, respectively. (C) 2016 Elsevier B.V. All rights reserved.Article Citation - WoS: 24Citation - Scopus: 25A Novel Conducting Polymer Based on Terthienyl System Bearing Strong Electron-Withdrawing Substituents and Its Electrochromic Device Application(Elsevier Science Sa, 2008) Asil, Demet; Cihaner, Atilla; Algi, Fatih; Onal, Ahmet M.A novel conducting polymer bearing strong electron-withdrawing substituents (EWS) directly attached to the 3,4-positions of the thiophene ring was synthesized by electrochemical polymerization of diethyl 2,5-di(thiophen-2-yl)thiophene-3,4-dicarboxylate (SSS-Diester). The polymer (PSSS-Diester) was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The polymer has a reversible redox process and demonstrates a stable electrochromic behavior: reddish orange in the neutral state, brown in the intermediate state and green in the oxidized state. Optical density and response time of the dual-type electrochromic device based on PSSS-Diester were found to be 0.23 and 0.6 s at 623 nm, respectively. It is also noteworthy that the device shows good environmental and redox stability (i.e. 94% of the optical activity of the device retained after 500th switch). (c) 2008 Elsevier B.V. All rights reserved.Article Citation - WoS: 65Citation - Scopus: 67An Electrochromic and Fluorescent Polymer Based on 1-(1(Elsevier Science Sa, 2008) Cihaner, Atilla; Algi, FatihA novel polymer was synthesized by electrochemical polymerization of 1-(1-naphthyl)-2,5-di-2-thienyl-1H-pyrrole (SNS-1-NAPH). The corresponding polymer (PSNS-1-NAPH) was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The polymer has a very well-defined and reversible redox process in both organic and aqueous solutions. Furthermore, it shows stable electrochromic behavior; yellow in the neutral state, green in the intermediate state and violet in the oxidized state. PSNS-1-NAPH is soluble in common solvents. Although SNS-1-NAPH is almost nonfluorescent, its polymer is a yellow and/or green light emitter. (c) 2007 Elsevier B.V. All rights reserved.Article Citation - WoS: 16Citation - Scopus: 16A New Carborane Based Polymeric Electrochrome(Elsevier Science Sa, 2013) Cansu-Ergun, Emine Gul; Cihaner, AtillaNew electrochromic copolymers of 3,4-ethylenedioxythiophene and di(m-carboranyl thiophene) were synthesized, characterized and their electro-optical properties were reported. The copolymers were successfully prepared from various monomer feed ratios using electrochemical polymerization technique. It can be conjectured that electrochemical and optical properties of the copolymers can be adjusted by playing with monomer feed ratios. For example, the maximum wavelength of poly(3,4-ethylenedioxythiophene) at 600 nm can be shifted to lower values (i.e., 522 nm) by increasing the ratio of di(m-carboranyl thiophene) in the monomer mixture. The copolymer films also have low band gap values between 1.69 and 1.82 eV and showed electrochromic properties; purple when neutralized and transparent sky blue when oxidized. Also, during redox switching the films exhibited a percent transmittance change between 32% and 46% with a switching time between 1.0 s and 1.3 s. (C) 2013 Elsevier B.V. All rights reserved.Article Citation - WoS: 11Citation - Scopus: 14Electrochemical Synthesis of New Conducting Copolymers Containing Pseudo-Polyether Cages With Pyrrole(Elsevier Science Sa, 2007) Cihaner, AtillaConducting copolymers have been synthesized via electrochemical oxidation of pyrrole (Py) in the presence of monomer 1, 11 -bis(1,1-pyrrole)-3,6,9-trioxaundecane (I) in an electrolytic solution containing 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF(6)) dissolved in acetonitrile. It is observed that reversible redox behavior of poly(I-co-Py)s shifts to more positive potentials with the increasing amount of I in the comonomer mixture, indicating formation of a copolymer. It is also found that increasing the ratio of I in the comonomer mixture decreases the conductivity of the obtained polymer films. The dark electrical conductivity measurements in the temperature range of 300-100 K revealed the extrinsic type of conduction with activation energy values being in the range of 82.3-16.9 meV. (c) 2007 Elsevier B.V. All rights reserved.Article Citation - WoS: 26Citation - Scopus: 30Electrochemical Polymerization of 9-Fluorenecarboxylic Acid and Its Electrochromic Device Application(Elsevier Science Sa, 2008) Bezgin, Buket; Cihaner, Atilla; Onal, Ahmet M.Poly(9-fluorenecarboxylic acid) (PFCA) was synthesized by electrochemical oxidation of 9-fluorenecarboxylic acid (FCA) using a mixture of nitromethane and boron trifluoride diethyl etherate as the solvent and tetrabutylammonium tetrafluoroborate as the supporting electrolyte. An insoluble and conducting brownish-orange film was deposited on the electrode surface, both during repetitive cycling and constant potential electrolysis at 1.15 V. Characterization of the polymer film has been carried out using Fourier Transform Infrared spectroscopy technique and thermal behavior was studied via thermal gravimetric analysis. Structural analysis showed that the polymerization of FCA occurred at 2,7-position. Spectroelectrochemical behavior of the polymer film on indium tin oxide working electrode was studied by recording the electronic absorption spectra, in-situ, in monomer-free electrolytic solution at different potentials and it is found that the PFCA film can be reversibly cycled between 0.0 V and 1.2 V Furthermore, a dual type electrochromic device based on PFCA was constructed and its spectroelectrochemical properties were investigated. The electrochromic device exhibits color change from transparent to dark blue with a good open circuit memory. (c) 2008 Elsevier B.V. All rights reserved.Article Citation - WoS: 16Citation - Scopus: 16Synthesis and electropolymerization of thieno[3,4-c]pyrrole-4,6-dione based donor-acceptor-donor type monomers(Elsevier Science Sa, 2020) Cakal, Deniz; Cihaner, Atilla; Onal, Ahmet M.Two monomers containing thieno [3,4-c]pyrrole-4,6-dione (TP) acceptor units, namely 5-(2-ethylhexyl)-1,3-di (furan2-yl)-4H-thieno [3,4-c]pyrrole-4,6(5H)-dione (FTPF) and 5-(2-ethylhexyl)-1,3-di (selenophen-2-yl)-4H-thieno[3,4-c] pyrrole-4,6(5H)-dione (STPS), were synthesized via donor-acceptor-donor approach. Under the same template structure, the effect of heteroatom of the donor unit on redox and optical properties of the monomers and their corresponding polymers obtained via electrochemical method (PFTPF and PSTPS) were investigated. The results were also compared to their thiophene analogues 5-(2- ethylhexyl)-1,3-di (thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (TTPT) as the monomer and PTTPT as the polymer. Three monomers exhibited dual absorption bands one at high energy region due to the pi-pi* transition and the other one at low energy region which might be attributed to intramolecular charge transfer (ICT). An increase in ICT and a decrease both in the band gap and quantum yield was observed with increasing size of the heteroatomof the donor units. The oxidation potentials of the monomers and that of their corresponding polymer films were found to follow the order of decreasing aromatization energy from thiophene to furan (i.e thiophene > selenophene > furan). Also, heavy-atom substitution (PSTPS) effect showed itself by narrowing the optical band gap of the neutral state electrochromic polymer films: 1.90 eV for PFTPF, 1.82 eV for PTTPT and 1.76 eV for PSTPS.Article Citation - WoS: 25Citation - Scopus: 26Electrochemical Synthesis of Poly(3-Bromo and Its Device Application(Elsevier Science Sa, 2007) Cihaner, Atilla; Onal, Ahmet M.A functionalized thiophene containing both an electron withdrawing and an electron donating group, 3-bromo-4-methoxythiophene (BrMeOTh) was succesfully polymerized in acetonitrile containing 0.1 M tetrabutylammonium tetrafluoroborate (TBABF4) electrolyte via electrochemical oxidation of the corresponding monomer. BrMeOTh exhibits a lower oxidation potential (1.68 V vs Ag/AgCl) than thiophene (2.05 V vs Ag/AgCl). Spectroelectrochemical properties of poly(3-bromo-4-methoxythiophene) (PBrMeOTh) was investigated in situ recording the electronic absorption spectra of the polymer film coated on indium-tin oxide (ITO) at various potentials. The maximum transmittance difference between the oxidized and reduced states was measured as 39.2% and the time required to attain 90% of the total transmittance difference was found to be 1.2 s. Both cyclic voltammetric and spectroelectrochemical studies showed that the polymer exhibit a lower oxidation potential, a relatively narrow band gap, a stable conducting state and a higher degree of electrochemical reversibility. It is also found that, as synthesized PBrMeOTh films possess a linear structure along the polymer backbone. Moreover, dual type electrochromic device of PBrMeOTh with poly(3,4-diethylenedioxythiohene) (PEDOT) was constructed and its spectroelectrochemical, electrochromic switching and open circuit stability were investigated. Dual electrochromic device showed a good optical contrast and distinctive color changes with the ability of good switching times (1.1 s) under atmospheric pressure. (c) 2006 Elsevier B.V. All rights reserved.Article Citation - WoS: 2Citation - Scopus: 2New electrochromic copolymers based on spiro bipropylenedioxythiophene and 3,4-ethylenedioxythiophene(Elsevier Science Sa, 2014) Pekel, Lutfiye Canan; Karabay, Bads; Cihaner, AtillaTwo alkylenedioxythiophene derivatives, Spiro bipropylenedioxythiophene (Spiro-BiProDOT) and 3,4-ethylenedioxythiophene (EDOT), were integrated electrochemically in order to attain low band gap electrochromic copolymers. EDOT has a functionality of two, which causes a linear polymer, whereas Spiro-BiProDOT has a functionality of four and its polymerization results in a network polymer. Therefore, by playing the monomer feed ratio, the crosslink degree can be adjusted for the copolymers obtained electrochemically from EDOT and Spiro-BiProDOT monomers in an electrolyte solution of 0.1 M tetrabutyl ammonium hexafluorophosphate dissolved in dichloromethane. It was found that copolymers showed different electrochemical and optical properties at their various redox states when compared to their homopolymers. For example, they could be switched from dark blue in the neutral state to reddish blue at intermediate state and finally to transparent blue in the oxidized state with 45-51% of the transmittance change at 575-595 nm. pi-pi* transition bands of the copolymers can be shifted to higher wavelengths when compared to poly(Spiro-BiProDOT) by increasing the amount of the EDOT units in the polymer backbone. They have low band gaps in the range of 1.65 and 1.73 eV. (C) 2014 Elsevier B.V. All rights reserved.
