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Article Citation - WoS: 7Citation - Scopus: 9Pyrrole Coupling Chemistry: Investigation of Electroanalytic, Spectroscopic and Thermal Properties of N-Substituted Poly(bis-Pyrrole) Films(Royal Soc Chemistry, 2013) Mert, Olcay; Demir, Ayhan S.; Cihaner, AtillaAn etheric member of N-linked polybispyrroles (PolybisPy) based on 1-(3-(2-(2-(3-(1H-pyrrol-1-yl)propoxy)ethoxy)ethoxy)propyl)-1H-pyrrole (1) was electrochemically synthesized for the versatile investigation of its exciting electrochromic and ion receptor properties. It has been fully characterized by electroanalytic, spectroscopic, thermal, and four-probe techniques. It was thereby found that P1 shows strong stability, and a reversible redox process as well as a good electrochromic material property; transparent yellow in the neutral state, light pink in the intermediate state, and blue in the oxidized state. Also, the corresponding polymer (P1) exhibited a selective voltammetric response towards Na+ among the alkali series in an organic medium. Moreover, P1 film was employed for the detection of Ag+ ions in the solution with cyclic voltammetry without precipitants or complexing ligands, and SEM images confirmed the deposition of metallic silver on the film surface. These prominent features also make P1 a good candidate for many practical uses, such as the recovery of metals and ion sensors.Article Citation - WoS: 6Citation - 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: 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: 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: 13Citation - Scopus: 14Thermally Highly Stable Polyhedral Oligomeric Silsesquioxane (poss)-Sulfur Based Hybrid Inorganic/Organic Polymers: Synthesis, Characterization and Removal of Mercury Ion(Royal Soc Chemistry, 2022) Berk, Hasan; Kaya, Murat; Cihaner, AtillaElemental sulfur was copolymerized with octavinyl polyhedral oligomeric silsesquioxane (OV-POSS) cages in diglyme solution via the inverse vulcanization method and characterized using NMR and FTIR spectroscopic techniques. The polysulfur copolymer called poly(sulfur-random-octavinyl polyhedral oligomeric silsesquioxane) (poly(S-r-OV-POSS)) was cured successfully sequentially at 170, 200 and 230 degrees C without changing the structure of the POSS cages in the polymer backbone. Highly crosslinked poly(S-r-OV-POSS) polymer cured at 200 and 230 degrees C exhibited high thermal stability at high temperatures; the loss of the samples was only 10% weight at 400 degrees C and 27% at 800 degrees C. Finally, the feasibility of poly(S-r-OV-POSS) as an adsorbent for the removal of Hg(ii) ions, as an example of a toxic heavy metal, from an aqueous solution was investigated. Optimization of the pH of the solution and contact time was performed and almost all Hg(ii) ions were collected from the aqueous solution at pH = 7 in 1 h (99% adsorption).Article Citation - WoS: 17Citation - Scopus: 18A Glow in the Dark: Synthesis and Electropolymerization of a Novel Chemiluminescent Terthienyl System(Royal Soc Chemistry, 2009) Asil, Demet; Cihaner, Atilla; Onal, Ahmet M.The synthesis and characterization of a unique (electro)-chemiluminescent monomer based on a terthienyl system, and its corresponding polymer which is the first example of an electro-active chemiluminescent polymer bearing a pyridazine appendage, are described.
