9 results
Search Results
Now showing 1 - 9 of 9
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).Article Citation - WoS: 11Citation - Scopus: 11Electrochemical and Optical Properties of Substituted Phthalimide Based Monomers and Electrochemical Polymerization of 3,4-Ethylenedioxythiophene Oligomeric Silsesquioxane (poss) Analogue(Elsevier Sci Ltd, 2019) Cakal, Deniz; Ertan, Salih; Cihaner, Atilla; Onal, Ahmet M.A new series of donor-acceptor-donor type trimeric monomers bearing substituted phthalimide units as acceptor units and thiophene and 3,4-ethylenedioxythiophene (EDOT) as donor units was synthesized and characterized. The strength of acceptor units and intramolecular charge transfer between donor and acceptor units were investigated by using electrochemical and optical methods. The main advantage of phthalimide unit over other acceptor units is the ease of its functionalizability. Thus, utilizing this property, a phthalimide derivative (E2P-POSS) bearing polyhedral oligomeric silsesquioxane (POSS) cage was introduced successfully with EDOT and polymerized electrochemically. The corresponding electroactive polymer, PE2P-POSS, has a band gap of 1.72 eV and is an electrochromic polymer: gray when neutralized and eggplant purple when oxidized.Article Citation - WoS: 30Citation - Scopus: 31A New Low-Voltage Polymeric Electrochromic(Elsevier Sci Ltd, 2010) Pamuk, Melek; Tirkes, Seha; Cihaner, Atilla; Algi, FatihDesign, synthesis, and properties of a novel donor-acceptor-donor type low-voltage-driven green polymeric electrochrome, P1, which is based on 8-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-11-(2,3-dihydrothieno[3,4-b][l,4]dioxin-7-yl)acenaphtho[1,2-b]quinoxaline (1) are highlighted. It is noted that P1 has an ambipolar (n- and p-doping processes) character in 0.1 M tetrabutylammonium hexafluorophosphate/dichloromethame solution and switches to a transmissive blue state upon oxidation. Furthermore, this new polymeric electrochromic candidate exhibits high redox stability, high coloration efficiency and/or contrast ratio, high percent transmittance (%T) and low response time (1.0 s) with a band gap of 1.10 eV-1.25 eV. (C) 2009 Elsevier Ltd. All rights reserved.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: 24Citation - Scopus: 23Synthesis and Electrochemical Polymerization of D-A Type Monomers With Thieno [3,4-c] Pyrrole-4,6 Acceptor Unit(Elsevier Sci Ltd, 2018) Cakal, Deniz; Ertan, Salih; Cihaner, Atilla; Onal, Ahmet M.In this study, three new donor-acceptor-donor type monomers bearing 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno [3,4-c]pyrrole- 4,6(5H)-dione (A) as an acceptor unit and thiophene, 3,4-ethylenedioxythiophene (EDOT) and 3,3-didecy1-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (didecyl-ProDOT) as donor units were synthesized via Stille cross-coupling reaction and their electrochemical polymerization by repetitive cycling was reported. The electrochemical and optical properties of the monomers ((5-(2-ethyl-liexyl)-1,3-di(thienyl-2-yl)-4H-thienolr-3,4-cl pyrrole-4,6(5H)-dione (TAT), 1,3-bis(2,3-dihydrothieno[3,4-1)] (1,4]dioicin-5-yl)-5-(2-ethylhexyl)-4H-thieno(3,4-c) pyrrole-4,6-(5H)-dione (EAE) and 1,3-bis(3,3-didecyl-3,4-dihydro-2H-thieno[3,4-1)111,41-dioxepin-6-yl)-5-(2-ethylhexyl)-4H-thieno[3,4-apyrrole-4,6(5H)-dione (PAP)) and their corresponding polymers called PTAT, PEAE and PPAP were investigated and it was found that EDOT units containing monomer and polymer (EAE and PEAE) have lower oxidation potentials and lower band gap value as compared to didecyl-ProDOT and thiophene units containing monomers and polymers (PAP, TAT and PPAP, PTAT). Spectroelectrochemical investigations conducted on electrochemically obtained polymer films revealed that polymer films exhibited electrochromic behaviors: brick red to gray for PTAT, blue/violet to highly sky blue for PEAE and blue to highly light blue for PPAP in their neutral and oxidized states, respectively. Moreover, PAP was also polymerized chemically using FeC13 as an oxidizing agent. Both chemically and electrochemically obtained PPAP were found to be soluble in some organic solvents and their dichloromethane solutions can be reversibly oxidized and reduced using antimony pentachloride and hydrazine hydrate solutions, respectively.Article Citation - WoS: 13Citation - Scopus: 13Effect of the Donor Units on the Properties of Fluorinated Acceptor Based Systems(Elsevier Sci Ltd, 2021) Cakal, Deniz; Akdag, Akin; Cihaner, Atilla; Onal, Ahmet M.A new series of monomers in the donor-acceptor-donor array, namely 5-fluoro-4,7-di(furan-2-yl)benzo[c][1,2,5] thiadiazole (F2BT-F), and 5-fluoro-4,7-di(selenophen-2-yl)benzo[c][1,2,5] thiadiazole (S2BT-F), bearing 5-fluorobenzo[c][1,2,5]-thiadiazole as the acceptor moiety and furan and selenophene as the electron donating groups was synthesized and polymerized electrochemically. To compare heteroatom effect, thiophene analogue of newly synthesized (FBT)-B-2-F and S2BT-F namely, (5-fluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5] thiadiazole (T2BT-F)) and its corresponding polymer were also synthesized. Effect of donor units on the electrochemical and optical properties of fluorinated acceptor based systems was investigated in terms of the effect of different sized heteroatoms in five-membered rings on the dihedral angle and planarity. Theoretical calculations also suggested a deviation from planarity upon fluorination. Moreover, electrochemically obtained polymers possess low bandgap values (1.62 eV-1.68 eV for PF2BT-F and PS2BT-F, respectively) and exhibited electrochromic properties with relatively low switching times.Article Citation - WoS: 14Citation - Scopus: 14A novel terthienyl based polymer electrochrome with peripheral BODIPY(Elsevier Sci Ltd, 2012) Algi, Fatih; Cihaner, AtillaDesign, synthesis and electropolymerization of a new hybrid material based on terthienyl system bearing BODIPY appendage are reported. This electrochemically polymerized unique combination readily gives an electrochromic polymer with a narrow optical band gap (1.71 eV). The electrochrome exhibits purple color when neutralized and sky blue color when oxidized in a monomer-free electrolyte solution containing 0.1 M tetrabutylammonium tetrafluoroborate dissolved in acetonitrile. Spectroscopic and electrochemical features of the electroactive polymer electrochrome indicate that it is a promising candidate for electrochromic device and display applications. (C) 2012 Elsevier Ltd. All rights reserved.Article Citation - WoS: 3Citation - Scopus: 2Polyhedral Oligomeric Silsesquioxane Cage Integrated Soluble and Fluorescent Poly(3,4-Propylenedioxythiophene) Dye(Elsevier Sci Ltd, 2021) Ertan, Salih; Kaya, Murat; Cihaner, AtillaA new analog of poly (3,4-propylenedioxythiophene) conjugated polymers called PProDOT-POSS, where polyhedral oligomeric silsesquioxane (POSS) nanocage with alkyl substitutions was integrated on the bridge of 3,4-propylenedioxythiophene unit and its structure was confirmed by spectroscopic techniques, was reported. The polymers were synthesized via both chemical and electrochemical polymerization techniques. While chemical polymerization was carried out in the presence of anhydrous FeCl3 as an oxidant, a solution of 0.1 M tetrabutylammonium hexafluoride electrolyte dissolved in a mixture of dichloromethane and acetonitrile (1/3: v/v) was used as an electrolyte solution for electrochemical polymerization. Electro-optical properties of the corresponding polymers were characterized by using electroanalytical techniques such as cyclic voltammetry and square wave potentiometry, and spectrophotometric methods like ultraviolet-visible and fluorescent spectrophotometry. Corresponding polymers obtained both electrochemically and chemically are soluble completely in common organic solvents such as chloroform, toluene, dichloromethane, tetrahydrofuran, etc. Polymer samples both in film and solution forms can be doped/dedoped reversibly by using a chemical oxidant or an external potential. The optical bandgap of the neutral polymer film with a maximum absorption band at 555 nm was calculated as 1.95 eV. Polymers have fluorescent property and excited polymers represented a red/orange light with an emission band centered at 605 nm in toluene. Also, PProDOT-POSS polymers have electrochromic properties under external potentials and they have an optical contrast of 55% at 555 nm between their neutral and oxidized states. Upon oxidation, they showed high transparency and they can switch between redox states in a short time (switching time = similar to 1.0 s) as well as high coloration efficiency (502 cm(2)/C for 95% switching). It can be concluded that POSS based PProDOT polymers can be good candidates for optoelectronic and bioelectronics applications. Short Abstract for Paper Submission: A new analog of poly (3,4-propylenedioxythiophene) conjugated polymers called PProDOT-POSS, was reported with the integrated of alkyl-substituted polyhedral oligomeric silsesquioxane nanocage structure. The polymers were synthesized via both chemical and electrochemical polymerization techniques. Corresponding polymers obtained both electrochemically and chemically are soluble completely in common organic solvents such as chloroform, toluene, dichloromethane, tetrahydrofuran, etc. Polymer samples both in film and solution forms can be doped/dedoped reversibly by using a chemical oxidant or an external potential. The optical bandgap of the neutral polymer film with a maximum absorption band at 555 nm was calculated as 1.95 eV. Polymers have fluorescent property and excited polymers represented a red/orange light with an emission band centered at 605 nm in toluene.
