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Article Citation - WoS: 1Citation - Scopus: 1Synthesis and Characterization of New Dithienosilole Based Copolymers(Electrochemical Soc inc, 2016) Karabay, Lutfiye Canan; Al-Jumaili, Mohammed; Cihaner, Atilla2-Ethylhexyl substituted dithienosilole based soluble polymers including thiophene (1) and bithiophene (2) units were synthesized via Stille coupling reaction. The presence of 2-ethylhexyl substituents on the silole ring gave solubility property to the polymers in common solvents. According to gel permeation chromatography measurements, the weight average molecular weights of the polymers 1 and 2 were found to be as 70,977 with a polydispersity index of 2.30 and 110,439 with a PDI of 1.42, respectively. Fluorescent polymers in toluene solution have maximum emisssion bands at 634 nm for the polymer 1 and 613 nm for the polymer 2. Chemical and electrochemical doping of the polymers in the solution and in the film forms were monitored by using ultraviolet-visible spectroscopic technique. The polymers exhibited chromic (chemochromic and electrochromic) properties. While the colors of the neutral polymer films are purple for the polymer 1 and reddish brown for the polymer 2, both polymers are transparent sky blue at their oxidized states. The bandgaps of polymers in film forms were calculated as 1.81 eV for the polymer 1 and 1.92 eV for the polymer 2. Also, electrochromic device applications of the polymers were done. Electrochemical and optical behaviors of the polymers demonstrated that they can be good candidates for optoelectronic applications. (C) 2016 The Electrochemical Society. All rights reserved.Master Thesis Yağ Asitlerinden Yüksek Kükürt İçerikli Polimerik Malzemelerin Sentezi ve Karakterizasyonu(2021) Berk, Hasan; Cihaner, AtillaDoğal kaynaklardan ve petrol rafinerilerinden elde edilen elementel kükürt, yaygın olarak bulunabilen ve pahalı ve zehirli olmayan bir malzeme olmasına rağmen, onun için büyük ölçekli üretken kullanımlar bulmak önemli bir ilerleme olacaktır. Öte yandan, gelecekte bitkisel yağların yenilenebilir kaynaklardan polimer üretiminde kilit rol oynaması beklenmektedir. Bu çalışmada, çeşitli miktarlarda yağ asitleri (oleik asit (OA), linoleik asit (LA) ve linolenik asit (LnA)) içeren yüksek kükürt içerikli yeni bir polimer serisi ters vulkanizasyon yöntemi ile sentezlenmiş ve başarılı bir şekilde karakterize edilmiştir. Özellikle, çift bağların ve serbest alkil zincirlerinin polikükürt kopolimerleri üzerindeki etkisi, bir çift bağlı OA, iki çift bağlı LA ve üç çift bağlı LnA kullanılarak sistematik olarak araştırılmıştır. İlgili kopolimerler yaygın organik çözücülerde çözünür, işlenebilir ve elektroaktiftir. Öte yandan, polimer yapısında yağ asitlerinin bulunması nedeniyle, kopolimerler reaktif fonksiyonel birimlere (karboksilik grup-COOH) sahiptir ve diol ile kimyasal modifikasyonları ester bağlarının oluşumuna yol açar. Bu post polimerizasyon, yüksek moleküler ağırlıklı yeni polimerlerin elde edilmesi ile sonuçlanır. Son olarak, kopolimerlerin ağır metal iyonlarının (Paladyum (II) ve Cıva (II)) uzaklaştırılmasında ve kullanımı test edilmiştir. Sonuçlar, polimerlerin ağır metal iyonu uzaklaştırma için potansiyel malzeme olabileceğini göstermiştir.Article Citation - WoS: 28Citation - Scopus: 30Functionalized Polysulfide Copolymers With 4-Vinylpyridine Via Inverse Vulcanization(Elsevier Science Bv, 2019) Berk, Hasan; Balci, Burcu; Ertan, Salih; Kaya, Murat; Cihaner, AtillaA new series of functional polysulfide copolymers called poly(sulfur-random-4-vinylpyridine) (poly(S-r-4VP)) was synthesized via inverse vulcanization technique by ring opening polymerization of elemental sulfur in the presence of 4-vinylpyridine (4VP). The corresponding copolymers can be post functionalized by using amine group in 4VP unit to get polymers bearing various properties. Elemental sulfur was heated up to 160 degrees C and 4VP was added slowly to a clear yellowish orange colored liquid at this temperature. The reaction mixture was vitrified to form a reddish-brown polymeric material at 180 degrees C in 1 h. The products were characterized by using FTIR, NMR, and Raman spectroscopic techniques. Poly(S-r-4VP) copolymers are soluble in common solvents like dichloromethane, chloroform and tetrahydrofuran. Weight-average molecular weights of poly(S-r-4VP) copolymers with different wt% 4VP were measured by using gel permeation chromatography technique. The polysulfide copolymers with different wt% 4VP have high weight-average molecular weights with polydispersity indeces (PDI) in a range from 1.88 to 4.06 measured by gel permeation chromatography. Post functionalization of the copolymer with 50 wt% 4VP as an example was performed successfully by using alkyl bromide to get N-alkyl quaternized 4VP in polymer backbone.Article Citation - WoS: 52Citation - Scopus: 57Members of Cmy Color Space: Cyan and Magenta Colored Polymers Based on Oxadiazole Acceptor Unit(Amer Chemical Soc, 2012) Ozkut, Merve Icli; Algi, Melek Pamuk; Oztas, Zahide; Algi, Fatih; Onal, Ahmet M.; Cihaner, AtillaIn this study, three novel oxadiazole-based polymers were synthesized and their electrochemical and optical properties were investigated. The polymers were found to have both p- and n-type doping properties accompanied by electrochromic response. Two polymer films exhibit cyan and magenta colors, which constitute two legs of CMY color spaces, in their neutral states and they are soluble in common-organic solvents. According to the color mixing theory, all colors in the visible spectrum including black color can be obtained by using these polymers with a yellow colored electrochromic polymer. Among these polymers, the polymer bearing propyledioxythiophene donor units has some superior properties like high stability (it retains 94% of its electroactivity after 2000 cycles), solubility, and high coloration efficiency (230 cm(2)/C), whereas as expected ethylenedioxythiophene containing one has the lowest band gap as 1.08 eV.Article Citation - WoS: 1Citation - Scopus: 1Electrochemical Polymerization and Characterization of Polyether-Substituted Aniline Derivatives(Wiley, 2007) Tirkes, Seha; Cihaner, Atilla; Oenal, Ahmet M.New compounds consisting of aniline units linked by polyether bridges have been synthesized and their electrochemical polymerization was performed via constant potential electrolysis and cyclic voltammetry in an aqueous solution containing 3.0 moI L-1 H2SO4. Chemical polymerization was carried out using (NH4)(2)S2O8 as oxidizing agent. It was found that both methods gave the same polymer product without any cleavage of the polyether bridge between aniline rings. The polymers were characterized using the Fourier transform infrared spectroscopic technique and the thermal behavior of electrochemically prepared polymers was investigated using thermogravimetric analysis. Spectroelectrochemical properties of the films were investigated using the in situ UV-visible spectroscopic technique. (c) 2007 Society of Chemical Industry.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: 20Citation - Scopus: 22Electrochemical and Optical Properties of an Azo Dye Based Conducting Copolymer(Tubitak Scientific & Technological Research Council Turkey, 2009) Cihaner, Atilla; Algi, FatihThe electrochemical and optical properties of a novel conducting copolymer called poly(2,5'-dimethyl-[4-(2,5-di-thiophen-2-yl-pyrrol-1-yl)-phenyl]azobenzene-co-(3,4-ethylenedioxythiophene)) (poly(1-co-EDOT)) are reported. Electrochemically synthesized poly(1-co-EDOT) based on the azo dye has a well-defined and reversible redox couple (0.37 V vs. Ag/AgCl) with good cycle stability. The copolymer film exhibits high conductivity (13 S/cm) as well as electrochromic behavior (magenta when neutralized and transmissive sky blue when oxidized). Furthermore, electro-optically active copolymer film has a low band gap of 1.79 eV with a pi-pi* transition at 555 nm.Article Side Chain Effect on the Electrochemical and Optical Properties of Tpd Based Donor Acceptor Donor Type Monomers and Polymers(Molecular Systems Design and Engineering, 2023) Çakal, Deniz; Demir Arabacı, Elif; Yıldırım, Erol; Cihaner, Atilla; Önal, Ahmet M.In organic π-conjugated materials, side chains play great roles that are 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 TPD acceptor with a new side chain, fluorene, 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, have been discussed in comparison to each other. Notably, it was discovered that TPD acceptor unit can be modified by any functional group other than common alkyl chains to impart new functionalities by keeping their superior optoelectronic properties. New kind of side chains can be used to tune the physical characteristics such as solubility, absorption, emission and molecular packing. In this paper, fluorene-appended monomers as a new class of D-A-D type π-conjugated molecules were studied and it was found that E(Fl) and P(Fl) exhibited resonable quantum yields and their corresponding polymers revealed ambipolar character with slightly lower band gap as compared to the previous analougs 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 to improve next-generation organic π-conjugated materials with the desired properties.Article Synthesis and Electropolymerization of a Selenophene Based Chemiluminescent Monomer and Its Use in Blood Detection(Elsevier Sci Ltd, 2025) Balci, Burcu; Cakal, Deniz; Cihaner, AtillaA new selenophene based trimeric chemiluminescent compound, namely 5,7-di(selenophen-2-yl)-2,3-dihydrothieno[3,4-d]pyridazine-1,4-dione (S2T-Lum), was synthesized in two steps via electron donor-acceptor-donor approach. Its chemiluminescent reaction with hydrogen peroxide was investigated in an alkaline solution in the presence of various catalysts such as different metal ions, hemin and blood samples and the results were compared with its thiophene analogue (T2T-Lum) and luminol. It was found that S2T-Lum was very sensitive to copper(II) and iron(III) ions, and blood samples. Also, it can be easily concluded that S2T-Lum as a new member of luminol type compounds is a potential candidate for the detection of blood findings in forensic science. Furthermore, S2T-Lum has an irreversible oxidation peak at 1.28 V vs Ag/AgCl, which is responsible from its electropolymerization. S2T-Lum was successfully polymerized electrochemically via potentiodynamic electrolysis without cleavage of its chemiluminescent active appendage. To the best of our knowledge, its corresponding polymer PS2T-Lum film is the first member of selenophene based luminol type electroactive polymers.Article Citation - WoS: 8Citation - Scopus: 8Improvement of Optical Properties and Redox Stability of Poly(3,4-Ethylenedioxythiophene)(Elsevier Sci Ltd, 2018) Ertan, Salih; Cihaner, AtillaIn order to improve the optical properties and redox stability of poly(3,4-ethylenedioxythiophene) (PEDOT) without changing its electrochemical and electrochromic behaviour, it was supported with alkyl-substituted polyhedral oligomeric silsesquioxane (POSS) cage. The corresponding copolymers were obtained electrochemically via potentiostatic or potentiodynamic methods and compared to the parent homopolymers. Electrochemical polymerization of EDOT and POSS containing EDOT called EDOT-POSS in various monomer feed ratios was performed in an electrolyte solution of 0.1 M TBAPF(6) dissolved in a mixture of dichloromethane and acetonitrile (1/3: v/v). Just as PEDOT, the copolymers represented the similar band gap (1.61 eV), redox and electrochromic behaviors. On the other hand, when compared to the parent PEDOT, the presence of POSS cages in the copolymer backbone improved the redox stability and optical properties of PEDOT such as higher percent transmittance change (65% at 621 nm), higher transparency at oxidized state, lower switching time (similar to 1.0 s) and higher coloration efficiency (463 cm(2)/C for 95% switching) as well as higher electrochemical stability (86% of its electroactivity retains after 1750 cycles under ambient conditions).
