Abstract
A polymer derived from poly-9-bis[4-(thiophen-3,4-yloxy)biphenyl)]-9H-carbazole containing a carbazole and thiophene group, abbreviated as B2, was synthesized via the oxidation method by using FeCl3 as an oxidant. Additionally, the electrochemical polymer of B2 was synthesized and coated onto an ITO–glass surface via electrochemical oxidative polymerization. The electrochemical synthesis of the polymer was performed in 0.05 M AN/LiClO4 solvent/electrolyte solution containing 0.1 M concentration of B2 between +0.3 and +1.4 V potentials. The compounds were characterized by FT-IR, NMR, and elemental analysis techniques. The spectroelectrochemical and electrochromic properties of this polymer were also investigated in 0.05 M AN/LiClO4 solvent/electrolyte solution for 200 s and at a constant potential of +1.4 V. Switching ability of this polymer was measured as the percent transmittance (∆T%) at its changing point of maximum contrast. Additionally, the scan rate study was performed at different scan rates: 400, 300, 200, 100, 50, 20 mV/s. According to the electrochromic measurements, the synthesized polymer had a light blue color when it was oxidized, and when it was reduced, it had a transparent color. As a result, the synthesized polymer P(B2) can be used to produce new polymeric electrochromic devices, and it can be considered a good candidate for applications of electrochromic devices (ECDs) because of its short response time of 3.5 s.
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Kaya İ, Aydın A (2012) A new approach for synthesis of electroactive phenol based polymer: 4-(2,5-Di(thiophen-2-yl)-1H-pyrrol-1-yl)phenol and its oxidative polymer. Prog Org Coat 73:239–249
Aydın A, Kaya İ (2012) Synthesis and characterization of yellow and green light emitting novel polymers containing carbazole and electroactive moieties. Electrochim Acta 65:104–114
Kaya İ, Bora E, Aydın A (2014) Synthesis and characterization of Schiff base derivative with pyrrole ring and electrochromic applications of its oligomer. Prog Org Coat 77:463–472
Aydın A, Kaya İ (2013) Syntheses of novel copolymers containing carbazole and their electrochromic properties. J Electroanal Chem 691:1–12
Aydın A, Kaya İ (2013) Syntheses, characterizations and electrochromic applications of polymers derived from carbazole containing thiophene rings in side chain with electrochemical and FeCl3 methods. Org Electron 14:730–743
Kocaeren AA (2015) Electrochemical synthesis and electrochromic application of a novel polymer based on carbazole. Org Electron 24:219–226
Kaya İ, Aydın A (2009) Synthesis, characterization, thermal degradation and electrical conductivity of oligo[2-(thien-2-ylmethylene) aminophenol] and oligomer-metal complexes. Chin J Polym Sci 27:465–477
Kaya İ, Aydın A (2011) Synthesis and characterization of the polyaminophenol derivatives containing thiophene in side chain:thermal degradation, electrical conductivity, optical-electrochemical, and fluorescent properties. J Appl Polym Sci 121:3028–3040
Kaya İ, Aydın A (2008) Synthesis, characterization, thermal stability, conductivity and band gaps of monomer and oligo-4-[(thien-2-ylmethylene)amino] phenol. e-Polymers 071:1–14
Kaya İ, Temizkan K, Aydın A (2013) Synthesis, characterization, thermal stability, conductivity and band gaps of monomer and oligo-4-[(thien-2-ylmethylene)amino] phenol. J Electroanal Chem 708:54–61
Kaya İ, Temizkan K, Aydın A (2013) Synthesis and characterization of aromatic and aliphatic ether bridged polymers containing carbazole moieties. Mater Sci Eng B 178:863–874
Kaya İ, Aydın A, Temizkan K (2013) Synthesis and characterization of a new dyestuff polymer soluble in alkaline aqueous media. Chin J Polym Sci 31:1632–1646
Zhang Y, Gao X, Li J, Tu G (2015) Highly selective palladium-catalyzed Suzuki coupling reaction toward chlorine-containing electroluminescence polymers. Dyes Pigments 120:112–117
He Y, Cai C (2011) Polymer-supported macrocyclic Schiff base palladium complex: An efficient and reusable catalyst for Suzuki cross-coupling reaction under ambient condition. Catal Commun 12:678–683
Liu H, Wu F, Zhao B, Meng L, Wang G, Zhang J, Shen P, Tan S (2015) Synthesis and photovoltaic properties of the acceptor pended push–pull conjugated polymers incorporating thieno[3,2–b] thiophene in the backbone chain or side chains. Dyes Pigments 120:44–51
Ming S, Zhen S, Liu X, Lin K, Liu H, Zhao Y, Lu B, Xu J (2015) Chalcogenodiazolo[3,4-c]pyridine based donor–acceptor–donor polymers for green and near-infrared electrochromics. Polym Chem 6:8248–8258
Lin K, Ming S, Zhen S, Zhao Y, Lu B, Xu J (2015) Molecular design of DBT/DBF hybrid thiophenes π-conjugated systems and comparative study of their electropolymerization and optoelectronic properties: from comonomers to electrochromic polymers. Polym Chem 6:4575–4587
Koll DK, Taha AH, Giolando DM (2011) Photochemical “Self-healing” pyrrole based treatment of CdS/CdTe photovoltaics. Sol Energy Mater Sol Cells 95:1716–1719
Wang K, Zhang T, Hu Y, Yang W, Shi Y (2014) Synthesis and characterization of a novel multicolored electrochromic polymer based on a vinylene-linked EDOT-carbazole monomer. Electrochim Acta 130:46–51
Jiang Q, Zhen S, Mo D, Lin K, Ming S, Wang Z, Liu C, Xu J, Yao Y, Duan X, Zhu D, Shi H (2016) Design and synthesis of 9,9-dioctyl-9H-fluorene based electrochromic polymers. J Polym Sci Polym Chem 54:325–334
Thakur VK, Ding G, Ma J, Lee PS, Lu X (2012) Hybrid materials and polymer electrolytes for electrochromic device applications. Adv Mater 24:4071–4096
Beaujuge PM, Reynolds JR (2010) Color control in π-conjugated organic polymers for use in electrochromic devices. Chem Rev 110:268–320
Mi S, Wu J, Liu J, Zheng J, Xu C (2015) Donor–π-bridge–acceptor fluorescent polymers based on thiophene and triphenylamine derivatives as solution processable electrochromic materials. Org Electron 23:116–123
Padilla J, Österholm AM, Dyer AL, Reynolds JR (2015) Process controlled performance for soluble electrochromic polymers. Sol Energy Mater Sol Cells 140:54–60
Cysewska K, Karczewski J, Jasiński P (2015) Influence of electropolymerization conditions on the morphological and electrical properties of PEDOT film. Electrochim Acta 176:156–161
Alévêque O, Levillain E, Sanguinet L (2015) Spectroelectrochemistry on electroactive self-assembled monolayers: cyclic voltammetry coupled to spectrophotometry. Electrochem Commun 51:108–112
Yan R, Jin B (2015) Investigation on the redox mechanism of polyaniline film in acid solution by in situ rapid-scan time-resolved infrared spectroelectrochemistry. J Electroanal Chem 743:60–67
Romero DB, Nüesch F, Benazzi T, Adès D, Siove A, Zuppiroli L (1997) Electroluminescence from carbazole dimers. Adv Mater 9:1158–1161
Kaya İ, Yıldırım M, Aydın A, Şenol D (2010) Synthesis and characterization of fluorescent graft fluorene-co-polyphenol derivatives: the effect of substituent on solubility, thermal stability, conductivity, optical and electrochemical properties. React Funct Polym 70:815–826
Kaya İ, Aydın A (2011) Synthesis and characterization of chelate polymers containing etheric diphenyl ring in the backbone: thermal, optical, electrochemical, and morphological properties. Polym Adv Technol 22:951–961
Cloutet E, Olivero C, Adès D, Castex M-C, Siove A (2002) Synthesis and blue luminescence of a soluble newly designed carbazole main-chain polymer. Polymer 43:3489–3495
Berton N, Fabre-Francke I, Bourrat D, Chandezon F, Sadki S (2009) Poly(bisthiophene-carbazole-fullerene) double-cable polymer as new donor-acceptor material: preparation and electrochemical and spectroscopic characterization. J Phys Chem B 113:14087–14093
Yılmaz MD, Aytun T, Frasconi M, Stupp SI, Stoddart JF (2014) Photocurrent generation from a low band-gap and green BODIPY-based electrochromic polymer. Synth Met 197:52–57
Guarin SAP, Skene WG (2007) Thermal, photophysical, and electrochemical characterization of a conjugated polyazomethine prepared by anodic electropolymerization of a thiophenoazomethine co-monomer. Mater Lett 61:5102–5106
Qiu D, Guo Y, Wang H, Bao X, Feng Y, Huang Q, Zeng J, Qiu G (2011) Synthesis, crystal structure, photophysical property and electropolymerization of Pt(II) complexes with carbazole-grafting 2-(2-pyridyl)benzimidazole. Inorg Chem Commun 14:1520–1524
Pernites R, Ponnapati R, Felipe MJ, Advincula R (2011) Electropolymerization molecularly imprinted polymer (E-MIP) SPR sensing of drug molecules: Pre-polymerization complexed terthiophene and carbazole electroactive monomers. Biosens Bioelectron 26:2766–2771
Söyleyici HC, Ak M, Şahin Y, Demikol DO, Timur S (2013) New class of 2,5-di(2-thienyl)pyrrole compounds and novel optical properties of its conducting polymer. Mater Chem Phys 142:303–310
Rughooputh SDDV, Nowak M, Hotta S, Heeger AJ, Wudl F (1987) Spectroscopic studies of soluble poly(3-alkylthienylenes). Macromolecules 20:212–215
Yang X, Chi L, Chen C, Cui X, Wang Q (2015) The nearly 100% filling of PEDOT in TiO2 nanotube array by a simple electropolymerization method. Phys E 66:120–124
Dispenza C, Sabatino MA, Deghiedy N, Casaletto MP, Spadaro G, Piazza S, El-Rehim HAA (2015) In-situ polymerization of polyaniline in radiation functionalized polypropylene films. Polymer 67:128–138
Neo WT, Ye Q, Lin TT, Chua SJ, Xu J (2015) 4,9-Dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-embedded electrochromic conjugated polymers with high coloration efficiency and fast coloration time. Sol Energy Mater Sol Cells 136:92–99
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Kocaeren, A.A. Synthesis and electrochromic performance of a novel polymer based on an oxidative polymer derived from carbazole and thiophene. J Polym Res 23, 66 (2016). https://doi.org/10.1007/s10965-016-0961-1
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DOI: https://doi.org/10.1007/s10965-016-0961-1