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Synthesis and electrochromic performance of a novel polymer based on an oxidative polymer derived from carbazole and thiophene

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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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References

  1. 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

    Article  CAS  Google Scholar 

  2. 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

    Article  Google Scholar 

  3. 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

    Article  CAS  Google Scholar 

  4. Aydın A, Kaya İ (2013) Syntheses of novel copolymers containing carbazole and their electrochromic properties. J Electroanal Chem 691:1–12

    Article  Google Scholar 

  5. 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

    Article  Google Scholar 

  6. Kocaeren AA (2015) Electrochemical synthesis and electrochromic application of a novel polymer based on carbazole. Org Electron 24:219–226

    Article  CAS  Google Scholar 

  7. 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

    Article  CAS  Google Scholar 

  8. 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

    Article  CAS  Google Scholar 

  9. 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

    Google Scholar 

  10. 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

    Article  CAS  Google Scholar 

  11. 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

    Article  CAS  Google Scholar 

  12. 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

    Article  CAS  Google Scholar 

  13. 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

    Article  CAS  Google Scholar 

  14. 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

    Article  CAS  Google Scholar 

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. 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

    Article  CAS  Google Scholar 

  18. 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

    Article  CAS  Google Scholar 

  19. 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

    Article  CAS  Google Scholar 

  20. 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

    Article  CAS  Google Scholar 

  21. 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

    Article  CAS  Google Scholar 

  22. Beaujuge PM, Reynolds JR (2010) Color control in π-conjugated organic polymers for use in electrochromic devices. Chem Rev 110:268–320

    Article  CAS  Google Scholar 

  23. 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

    Article  CAS  Google Scholar 

  24. Padilla J, Österholm AM, Dyer AL, Reynolds JR (2015) Process controlled performance for soluble electrochromic polymers. Sol Energy Mater Sol Cells 140:54–60

    Article  CAS  Google Scholar 

  25. 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

    Article  CAS  Google Scholar 

  26. Alévêque O, Levillain E, Sanguinet L (2015) Spectroelectrochemistry on electroactive self-assembled monolayers: cyclic voltammetry coupled to spectrophotometry. Electrochem Commun 51:108–112

    Article  Google Scholar 

  27. 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

    Article  CAS  Google Scholar 

  28. Romero DB, Nüesch F, Benazzi T, Adès D, Siove A, Zuppiroli L (1997) Electroluminescence from carbazole dimers. Adv Mater 9:1158–1161

    Article  CAS  Google Scholar 

  29. 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

    Article  CAS  Google Scholar 

  30. 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

    Article  CAS  Google Scholar 

  31. 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

    Article  CAS  Google Scholar 

  32. 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

    Article  CAS  Google Scholar 

  33. 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

    Article  Google Scholar 

  34. 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

    Article  Google Scholar 

  35. 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

    Article  CAS  Google Scholar 

  36. 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

    Article  CAS  Google Scholar 

  37. 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

    Article  Google Scholar 

  38. Rughooputh SDDV, Nowak M, Hotta S, Heeger AJ, Wudl F (1987) Spectroscopic studies of soluble poly(3-alkylthienylenes). Macromolecules 20:212–215

    Article  Google Scholar 

  39. 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

    Article  CAS  Google Scholar 

  40. 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

    Article  CAS  Google Scholar 

  41. 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

    Article  CAS  Google Scholar 

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Correspondence to Aysel Aydın Kocaeren.

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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

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