38 results
Search Results
Now showing 1 - 10 of 38
Article Citation - WoS: 61Citation - Scopus: 72A Blue To Highly Transmissive Soluble Electrochromic Polymer Based on Poly(3,4-Propylenedioxyselenophene) With a High Stability and Coloration Efficiency(Royal Soc Chemistry, 2011) Ozkut, Merve Icli; Atak, Samed; Onal, Ahmet M.; Cihaner, AtillaThe optical and electrochemical properties of a regioregular and soluble alkylenedioxyselenophene-based electrochromic polymer, namely poly(3,3-didecyl-3,4-dihydro-2H-selenopheno[3,4-b][1,4] dioxepine (PProDOS-C-10), which is synthesized by electrochemical polymerization, are highlighted. It is noted that this unique polymer has a low band gap (1.58 eV) and is exceptionally stable under ambient atmospheric conditions. Polymer films retain 97% of their electroactivity after 40 000 cycles. The percentage transmittance of a PProDOS-C10 film was found to be 56.4% at 638 nm and 55.8% at 700 nm. Furthermore, this novel soluble PProDOS-C10 polymer shows an electrochromic behavior: a color change from pure blue to a highly transparent state in a low switching time (1.0 s) during oxidation, with high coloration efficiencies (328 cm 2 C-1 at 638 nm and 319 cm(2) C-1 at 700 nm) when compared to its thiophene analogue.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: 4Citation - Scopus: 4Template-free microsphere and hollow sphere formation of polymethylanilines(Wiley, 2009) Icli, Merve; Onal, Ahmet M.; Cihaner, AtillaBACKGROUND: Microsphere and/or hollow sphere formation of methyl-substituted polyaniline derivatives was investigated via chemical polymerization where different sets of conditions were examined. It was found that a variety of parameters (e.g. types and concentrations of monomer and oxidant, polymerization time, solvent with and without acid) have a crucial influence on the morphology of the resulting polyaniline derivatives. RESULTS: Structures with desired morphologies (with or without microspheres and hollow spheres) may be obtained in a controlled manner by changing the parameters. Moreover, the electrochemical and optical properties of the polymers in the presence of acid and/or base were investigated via cyclic voltammetry and UV-visible and electron spin resonance spectroscopic techniques. It is noteworthy that the morphologies of microspheres and/or hollow spheres remained unchanged after repeated acid and base treatments. CONCLUSION: Micro/hollow spherical structures were successfully prepared via chemical polymerization of various substituted anilines by using ammonium persulfate as oxidant. It was found that the type of oxidant and monomers along with the polymerization time are quite important factors for the formation of micro/hollow spheres. Furthermore, hydrogen bond formation does not play any crucial role for the formation of these spheres. Chemically and electrochemically doped/dedoped states of microspheres and/or hollow spheres are very sensitive, and give rapid response towards vapours of HCl and NH3, which makes them amenable for use in sensors. (c) 2009 Society of Chemical IndustryArticle Citation - WoS: 2Citation - Scopus: 3Effect of Phthalimide and Thieno[3,4-C]pyrrole Acceptors on P-Conjugated Donor-Acceptor Monomers: Experimental and Theoretical Investigations of Photophysical and Electrochemical Properties(Pergamon-elsevier Science Ltd, 2023) Cakal, Deniz; Arabaci, Elif Demir; Yildirim, Erol; Cihaner, Atilla; Onal, Ahmet M.In this study, two novel donor-acceptor-donor monomers were synthesized by coupling a phthalimide (PI) acceptor unit with thiophene (T) and ethylenedioxythiophene (EDOT (E)) donor units. These two novel PI-based monomers, namely 2-(2-ethylhexyl)-4,7-di(thiophen-2-yl)isoindoline-1,3-dione (T-PI) and 4,7-bis(2,3-dihydrothieno[3,4-b] [1,4]dioxin-5-yl)-2-(2-ethylhexyl)isoindoline-1,3-dione (E-PI), were fully characterized via UV-vis and fluorescence spectroscopy as well as electrochemical methods, and the results were directly compared with those of previously synthesized thieno[3,4-c]pyrrole-4,6-dione (TPD)-based analogues to report the results for four classes of monomers. In this regard, the ef-fects of different donor groups and structural modifications in the acceptor unit as changed from PI to TPD have been investigated to reveal the precise effect of the donor and acceptor on the optical and electrochemical properties of the monomers. All monomers exhibits an intramolecular charge transfer band in the low energy region due to strong donor and acceptor interactions. The oxidation and reduction potentials of the monomers are found to vary depending on the strengths of both donor and acceptor units. PI-based monomers show more positive oxidation and less negative reduction potentials than TPD-based analogues. Similarly, thiophene-based analogues reveal the same trend in their oxidation and reduction potentials as compared to EDOT-based analogues. Lastly, PI-based monomers could not undergo polymerization via electrochemical method, unlike TPD-based monomers, since the dihedral angle arising between donor and PI acceptor disturbs molecular planarity significantly, as demonstrated by first principle calculations.(C) 2023 Elsevier Ltd. All rights reserved.Article Citation - WoS: 52Citation - Scopus: 59Furan and benzochalcogenodiazole based multichromic polymers via a donor-acceptor approach(Royal Soc Chemistry, 2013) Icli-Ozkut, Merve; Ipek, Halil; Karabay, Baris; Cihaner, Atilla; Onal, Ahmet M.Two new furan and benzochalcogenodiazole based monomers, namely 4,7-di(furan-2-yl) benzo[c][1,2,5]-selenadiazole (FSeF) and 4,7-di(furan-2-yl) benzo[c][1,2,5]thiadiazole (FSF), were designed and synthesized via a donor-acceptor-donor approach. The monomers were electrochemically polymerized via potentiodynamic or potentiostatic methods. The monomers and their polymers exhibited lower oxidation potentials (1.16 V and 1.06 V for monomers; 0.93 V and 0.80 V for polymers vs. Ag/AgCl) and red shifts of the whole dual-band absorption spectra upon moving from S to Se. Intramolecular charge transfer properties of the monomers and the polymers were demonstrated by using electroanalytical and optical methods. Also, the polymers PFSeF and PFSF were multicolored at different redox states and have low band gaps of 1.43 eV and 1.61 eV, respectively.Article Citation - WoS: 7Citation - Scopus: 7Electrochemical and optical properties of dicyclohexylmethyl substituted poly(3,4-propylenedioxythiophene) analogue(Wiley, 2018) Cakal, Deniz; Cihaner, Atilla; Onal, Ahmet M.An analogue of disubstituted 3,4-propylenedioxythiophenes, namely 3,3-bis(cyclohexylmethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin (ProDOT-CycHex(2)), was synthesized and its electrochemical polymerization was carried out successfully in an electrolyte solution of 0.1 M tetrabutylammonium hexafluorophosphate dissolved in a mixture of acetonitrile and dichloromethane (3/1: v/v). The corresponding polymer called PProDOT-CycHex(2) has a reduced band gap of 1.85 eV and an electrochromic property: blue/violet when neutralized and highly transparent when oxidized. Also, PProDOT-CycHex(2) film exhibited faster response time (0.7 s) and higher coloration efficiency (769 cm(2)/C) during oxidation when compared to its benzyl substituted analogue. (c) 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46214.Article Citation - WoS: 14Citation - Scopus: 16Electrosynthesis of Polyfuran in Acetonitrile-Boron Trifluoride-Ethyl Ether Mixture and Its Device Application(John Wiley & Sons inc, 2007) Tirkes, Seha; Onal, Ahmet M.Electrochemical polymerization of furan was achieved in acetonitrile/boron trifluoride/ethyl ether (CH3 CN/BF3/EE) mixture in the presence of tetrabutylammonium tetrafluoroborate via constant potential electrolysis at 1.4 V versus Ag/AgCl. Electrochemical behavior of furan was investigated in the same solvent mixture of varying ratios, utilizing cyclic voltammetry. Free-standing polyfuran (PFu) films were obtained in CH3CN/BF3/EE mixture (2/4/4; v/v/v) and characterized using FTIR spectroscopic technique. Spectroelectrochemical behavior of the PFu film was investigated by recording the electronic absorption spectra, in sitn, in monomer-free solution. It is observed that PFu film can be reversibly cycled between -0.1 V (gray) and + 0.6 V versus Ag-wire (gray color); however, this behavior diminishes in the presence of water. Electrochromic device application of PFu film with poly(ethylene dioxythiophene) was also studied. (c) 2006 Wiley Periodicals, Inc.Article Citation - WoS: 30Citation - Scopus: 32Effect of Fluorine Substituted Benzothiadiazole on Electro-Optical Properties of Donor-Acceptor Type Monomers and Their Polymers(Elsevier Sci Ltd, 2020) Cakal, Deniz; Ercan, Yunus Emre; Onal, Ahmet M.; Cihaner, AtillaA series of trimeric monomers bearing thiophene donor units and fluorinated analogues of benzothiadiazole acceptor units was synthesized via donor-acceptor-donor approach and polymerized electrochemically in order to investigate the effect of fluorine atom on electro-optical properties of both monomers and their corresponding polymers. All monomers exhibited solvatochromic and fluorescent properties. The introduction of fluorine atom into the conjugated backbone increased the oxidation potentials. Upon moving from nonfluorinated to fully fluorinated analogues, the oxidation potential shifts anodically from 1.30 V to 1.7 V. As in the case of monomers, the fluorine atom substitution also resulted in a decrease in the HOMO energy level of the corresponding polymers, leading to an increase in the electrochemical band gap energy (1.71-1.97 eV). This result can be attributed to deviations from planarity and also to decrease in the effective conjugation length. The polymeric film also exhibited electrochromic properties under various external potentials. Switching time and coloration efficiency values decreased with increasing number of fluorine atom substitution.Article Citation - WoS: 7Citation - Scopus: 6Side Chain Effect on the Electrochemical and Optical Properties of Thieno[3,4-c]pyrrole-4,6-dione Based Donor-Acceptor Donor Type Monomers and Polymers(Royal Soc Chemistry, 2023) Cakal, Deniz; Arabaci, Elif Demir; Yildirim, Erol; Cihaner, Atilla; Onal, Ahmet M.In organic pi-conjugated materials, side chains play great roles that impact far beyond solubility. In this work, we mainly focused on the synthesis of new donor-acceptor-donor (D-A-D) type conjugated monomers and their corresponding polymers appending thieno[3,4-c]pyrrole-4,6-dione (TPD) acceptor with a new side chain, fluorene (Fl), to investigate the side chain effect. In this context, to reveal the precise effect of the side chains on the optical and electrochemical properties of the monomers and polymers synthesized in this work, four series of D-A-D monomers, each containing a TPD core unit with a different side chain, are compared and discussed in relation to each other. Notably, it was discovered that the TPD acceptor unit can be modified with any functional group other than common alkyl chains to impart new functionalities by maintaining their superior optoelectronic properties. New types of side chains can be used to tune the physical characteristics, such as solubility, absorption, emission, and molecular packing. In this work, Fl-appended monomers as a new class of D-A-D type pi-conjugated molecules containing 3,4-ethylenedioxythiophene (EDOT (E)) and 3,4-propylenedioxythiophene (ProDOT (P)) donor units were studied and it was found that 1,3-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-5-(9H-fluoren-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (E(Fl)) and 1,3-bis(3,3-didecyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-6-yl)-5-(9H-fluoren-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (P(Fl)) exhibited reasonable quantum yields and their corresponding polymers revealed ambipolar character with slightly lower band gap as compared to the previous analogues containing other side chains. Observed experimental results were elucidated by first principle calculations. In this paper, we discussed that using side chain engineering is an effective strategy for improving next-generation organic pi-conjugated materials with the desired properties.Article Citation - WoS: 8Citation - Scopus: 8Electropolymerization and Ion Sensitivity of Chemiluminescent Thienyl Systems(Pergamon-elsevier Science Ltd, 2009) Asil, Demet; Cihaner, Atilla; Onal, Ahmet M.Redox driven chemiluminescent (CL) compounds based on thienyl and pyridazine systems, namely 2,3-dihydrothieno(3,4-d)pyridazine-1,4-dione (T-Lum) and 5,7-di-thiophen-2-yl-2,3-dihydrothieno[3,4-d]pyridazine-1,4-dione (TTT-Lum), were synthesized. Soluble compounds both in organic media and basic aqueous solution were found to give CL and electroluminescent (EL) reactions by the treatment of oxidants (H2O2 and KMnO4) and by an external potential pulse on the working electrode, respectively. Furthermore, the CL reaction can be speeded up by Fe3+ ion or blood samples. On the other hand, one of the compounds. TTT-Lum, can be polymerized successfully via electrochemically both in 0.1 M LiClO4/acetonitrile containing 5% of borontrifluoro diethylether (BF3-Et2O) and neat BF3-Et2O solution. The corresponding polymer film (PTTT-Lum) bearing CL units has a very stable and a well-defined reversible redox couple. Also, the electrochromic polymer film has a band gap of 1.74 eV and exhibits EL behavior. (C) 2009 Elsevier Ltd. All rights reserved.
