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Synthesis and electrochromic properties of epoxy materials containing triphenylamine units

  • Liping Hao
  • Wen Wang
  • Yan Sun
  • Haijun Niu
  • Yan Ji
Original Paper

Abstract

A series of novel aromatic epoxy resins are prepared from the epichlorohydrin (ECH) and di(4-hydroxybenzylideneamino) triphenylamine (DHB-TPA) monomers, which are synthesized from different triphenylamine (TPA)-containing diamines and p-hydroxybenzaldehyde. FT-IR, 1H NMR and UV–Vis absorption spectra are employed to characterize the chemical structures of the polymers. All the polymers are amorphous, soluble in a variety of common organic solvents. The thermal properties of the polymers are investigated by thermogravimetric analysis (TGA) indicating good thermal stabilities compared with conventional epoxy resins on behalf of the introduction of aromatic TPA groups. All the polymers exhibit excellent reversibility of electrochromic characteristics by continuous cyclic scans between 0 and 2.0 V with the color changing from green to blue. The polymers also display photoelectrical response. The above properties prove that the series of polymers exhibit high thermal stability, excellent reversibility of electrochromic characteristics and photoelectric behaviours, which can be prospective candidates as electrochromic materials and photoelectrical conversion materials.

Keywords

Triphenylamines Electrochromic properties Photoelectro conversions Epoxy resins 

Notes

Acknowledgments

The authors are grateful to the support of the National Science Foundation of China (Grant No. 51373049, 51372055, 51321061), Doctoral Fund of Ministry of Education of China (20132301120004).

Supplementary material

10965_2015_715_MOESM1_ESM.pdf (510 kb)
ESM 1 (PDF 510 kb)

References

  1. 1.
    Somani PR, Radhakrishnan S (2002) Electrochromic materials and devices: present and future. Mater Chem Phys 77:117–133CrossRefGoogle Scholar
  2. 2.
    Maier A, Rabindranath AR, Tieke B (2009) Fast-switching electrochromic films of zinc polyiminofluorene-terpyridine prepared upon coordinative supramolecular assembly. Adv Mater 21:959–963CrossRefGoogle Scholar
  3. 3.
    Mortimer RJ (1997) Electrochromic materials. Chem Soc Rev 26:147–156CrossRefGoogle Scholar
  4. 4.
    Rosseinsky DR, Mortimer RJ (2001) Electrochromic systems and the prospects for devices. Adv Mater 13:783–793CrossRefGoogle Scholar
  5. 5.
    Liu S, Kurth DG, Mohwald H, Volkmer D (2002) A thin-film electrochromic device based on a polyoxometalate cluster. Adv Mater 14:225–228CrossRefGoogle Scholar
  6. 6.
    Zhang T, Liu S, Kurth DG, Faul CFJ (2009) Organized nanostructured complexes of polyoxometalates and surfactants that exhibit photoluminescence and electrochromism. Adv Funct Mater 19:642–652CrossRefGoogle Scholar
  7. 7.
    Kiralp S, Camurlu P, Gunbas G, Tanyeli C, Akhmedov I, Toppare L (2009) Electrochromic conjugated polyheterocycles and derivatives—highlights from the last decade towards realization of long lived aspirations. J Appl Polym Sci 112:1082–1087CrossRefGoogle Scholar
  8. 8.
    Bijleveld JC, Verstrijden RAM, Wienk MM, Janssen RAJ (2011) Copolymers of diketopyrrolopyrrole and thienothiophene for photovoltaic cells. J Mater Chem 21:9224–9231CrossRefGoogle Scholar
  9. 9.
    Azens A, Granqvist CG (2003) Electrochromic smart windows: energy efficiency and device aspects. J Solid State Electrochem 7:64–68CrossRefGoogle Scholar
  10. 10.
    DuBois CJ, Abboud KA, Reynolds JR (2004) Electrolyte-controlled redox conductivity and n-type doping in poly(bis-EDOT-pyridine)s. J Phys Chem B 108:8550–8557CrossRefGoogle Scholar
  11. 11.
    Mortimer RJ, Dyer AL, Reynolds JR (2006) Electrochromic organic and polymeric materials for display applications. Displays 27:2–18CrossRefGoogle Scholar
  12. 12.
    Esmera EN, Tarkucb S, Uduma YA, Toppare L (2011) A naphthalene-based multi-electrochromic material and its neutral green electrochromic device. Mater Chem Phys 131:519–524CrossRefGoogle Scholar
  13. 13.
    Liou GS, Hsiao SH, Huang HM, Chang CW, Yen HJ (2007) Synthesis and photophysical properties of novel organo-soluble polyarylates bearing triphenylamine moieties. J Polym Res 14:191–199CrossRefGoogle Scholar
  14. 14.
    Cheng XF, Zhao JS, Cui CS, Fu YZ, Zhang XX (2012) Star-shaped conjugated systems derived from thienyl-derivatized poly(triphenylamine)s as active materials for electrochromic devices. J Electroanal Chem 677–680:24–30CrossRefGoogle Scholar
  15. 15.
    Krebs FC, Jørgensen M (2004) The effect of fluorination in semiconducting polymers of the polyphenyleneimine type. Synth Met 142:181–185CrossRefGoogle Scholar
  16. 16.
    Yang CJ, Jenekhe SA (1995) Group contribution to molar refraction and refractive index of conjugated polymers. Chem Mater 7:1276–1285CrossRefGoogle Scholar
  17. 17.
    Işık D, Santato C, Barik S, Skene WG (2012) Charge-carrier transport in thin films of p-conjugated thiopheno-azomethines. Org Electron 13:3022–3031CrossRefGoogle Scholar
  18. 18.
    Bourgeaux M, Skene WG (2007) A highly conjugated p- and n-type polythiophenoazomethine: synthesis, spectroscopic, and electrochemical investigation. Macromolecules 40:1792–1795CrossRefGoogle Scholar
  19. 19.
    Kaya İ, Yıldırım M, Aydın A (2011) A new approach to the schiff base-substituted oligophenols: the electrochromic application of 2-[3-thienylmethylene] aminophenol based co-polythiophenes. Org Electron 12:210–218CrossRefGoogle Scholar
  20. 20.
    Kaya İ, Bora E, Aydın A (2014) Synthesis and characterization of schiff base derivative with pyrrolering and electrochromic applications of its oligomer. Prog Org Coat 77:463–472CrossRefGoogle Scholar
  21. 21.
    Sek D, Iwan A, Jarzabek B, Kaczmarczyk B, Kasperczyk J, Mazurak Z, Domanski M, Karon K, Lapkowski M (2008) Hole transport triphenylamine − azomethine conjugated system: synthesis and optical, photoluminescence, and electrochemical properties. Macromolecules 41:6653–6663CrossRefGoogle Scholar
  22. 22.
    Iwan A, Palewicz M, Krompiec M, Grucela-Z M, Schab-B E, Sikora A (2012) Synthesis, materials characterization and opto (electrical) properties of unsymmetrical azomethines with benzothiazole core. Spectrochim Acta A 97:546–555CrossRefGoogle Scholar
  23. 23.
    Niu HJ, Huang YD, Bai XD, Li X, Zhang GL (2004) Study on crystallization, thermal stability and hole transport properties of conjugated polyazomethine materials containing 4,4 -bisamine-triphenylamine. Mater Chem Phys 86:33–37CrossRefGoogle Scholar
  24. 24.
    Ma LN, Cai JW, Zhao P, Niu HJ, Wang C, Bai XD, Wang W (2012) In situ preparation of composite from conjugated polyschiff bases and multiwalled carbon nanotube: Synthesis, electrochromic, acidochromic properties. Mater Chem Phys 133:333–339CrossRefGoogle Scholar
  25. 25.
    Ma LN, Niu HJ, Cai JW, Lian YF, Zhang CH, Wang C, Bai XD, Wang W (2013) Non-conjugated polyamines with near-infrared electrochromic and photoelectric response prepared via reducing PolySchiff bases by NaBH4. Sen Actua B Chem 188:117–126CrossRefGoogle Scholar
  26. 26.
    Lim B, Nah YC, Hwang JT, Ghim J, Vak D, Yun JM, Kim DY (2009) Synthesis of novel arylamine containing perfluorocyclobutane and its electrochromic properties. J Mater Chem 19:2380–2385CrossRefGoogle Scholar
  27. 27.
    Cheng SH, Hsiao SH, Su TH, Liou GS (2005) Novel aromatic poly (amine-imide) s bearing a pendent triphenylamine group: synthesis, thermal, photophysical, electrochemical, and electrochromic characteristics. Macromolecules 38:307–316CrossRefGoogle Scholar
  28. 28.
    Huang LT, Yen HJ, Liou GS (2011) Subsitituent effect on electrochemical and electrochromic behaviors of ambipolar aromatic polyimides based on aniline derivatives. Macromolecules 44:9595–9610CrossRefGoogle Scholar
  29. 29.
    Hsiao SH, Yeh SJ, Wang HM, Guo WJ, Kung YR (2014) Synthesis and optoelectronic properties of polyimides with naphthyldiphenylamine chromophores. J Polym Res 21:407–418CrossRefGoogle Scholar
  30. 30.
    Hsiao SH, Wang HM, Chang PC, Kung YR, Lee TM (2013) Novel organosoluble aromatic polyetheramides bearing triphenylamine moieties: synthesis, electrochemistry, and electrochromism. J Polym Res 20:154–163CrossRefGoogle Scholar
  31. 31.
    Hsiao SH, Guo WJ, Kung YC, Lee YJ (2011) Redox-active and electrochromic aromatic poly(amide-imide)s with 2,4-dimethoxytriphenylamine chromophores. J Polym Res 18:1353–1364CrossRefGoogle Scholar
  32. 32.
    Niu HJ, Cai JW, Zhao P, Wang C, Bai XD, Wang W (2013) Simple approach to regulate the spectra of novel kinds of polyazomethines containing bulky triphenylamine: electrochemistry, electrochromism and photophysical responsive to environment. Dyes Pigments 96:158–169CrossRefGoogle Scholar
  33. 33.
    Iwan A, Sek D (2011) Polymers with triphenylamine units: photonic and electroactive materials. Prog Polym Sci 36:1277–1325CrossRefGoogle Scholar
  34. 34.
    Li M, Wei YX, Zheng JM, Zhu D, Xu CY (2014) Highly contrasted and stable electrochromic device based on well-matched viologen and triphenylamine. Org Electron 15:428–434CrossRefGoogle Scholar
  35. 35.
    Du Q, Wei YX, Zheng JM, Xu CY (2014) Donor-π-bridge-acceptor type polymeric materials with pendant electron-withdrawing groups for electrochromic applications. Electrochim Acta 132:258–264CrossRefGoogle Scholar
  36. 36.
    John NAS, George GA (1994) Diglycidyl amine-epoxy resin networks: kinetics and mechanisms of cure. Prog Polym Sci 19:755–795CrossRefGoogle Scholar
  37. 37.
    Kandola BK, Biswas B, Price D, Horrocks AR (2010) Studies on the effect of different levels of toughener and flame retardants on thermal stability of epoxy resin. Polym Degrad Stab 95:144–152CrossRefGoogle Scholar
  38. 38.
    Zhang D, Jia D, Chen S (2009) Kinetics of curing and thermal degradation of hyperbranched epoxy (HTDE)/diglycidyl ether of bisphenol-A epoxy hybrid resin. J Therm Anal Calorim 98:819–824CrossRefGoogle Scholar
  39. 39.
    Mezzenga R, Boogh L, Manson JAE, Pettersson B (2000) Effects of the branching architecture on the reactivity of epoxy-amine groups. Macromolecules 33:4373–4379CrossRefGoogle Scholar
  40. 40.
    Liu ZG, Zhang G, Liu Z, Sun HC, Zhao CJ, Wang S, Li GB, Na H (2012) Synthesis and properties of an epoxy resin containing trifluoromethyl side chains and its cross-linking networks with different curing agents. Polym Degrad Stabil 97:691–697CrossRefGoogle Scholar
  41. 41.
    Chuang YW, Yen HJ, Liou GS (2013) A facile approach to multicolored electrochromic triarylamine-based thermoset epoxy materials with tunable intervalence charge transfer behavior. Chem Commun 49:9812–9814CrossRefGoogle Scholar
  42. 42.
    Vorländer D (1927) Über die Natur der Kohlenstoffketonen in Kristallin-flüssigen Substancen. Z Phys Chem 126:449–472Google Scholar
  43. 43.
    Ribera D, Mantecón A, Serra A (2002) Synthesis and crosslinking of a series of dimeric liquid-crystalline diglycidylester compounds containing imine groups. J Polym Sci Part A Polym Chem 40:4344–4356CrossRefGoogle Scholar
  44. 44.
    Rosu D, Cascaval CN, Mustata F, Ciobanu C (2002) Cure kinetics of epoxy resins studied by non-isothermal DSC data. Thermochim Acta 383:119–127CrossRefGoogle Scholar
  45. 45.
    Niu HJ, Luo PH, Zhang ML, Zhang L, Hao LN, Luo J, Bai XD, Wang W (2009) Multifunctional, photochromic, acidichromic, electrochromic molecular switch: novel aromatic poly(azomethine)s containing triphenylamine group. Eur Polym J 45:3058–3071CrossRefGoogle Scholar
  46. 46.
    Niu HJ, Kang HQ, Cai JW, Wang C, Bai XD, Wang W (2011) Novel soluble polyazomethines with pendant carbazole and triphenylamine derivatives: preparation, characterization and optical, electrochemical, electrochromic properties. Polym Chem 2:2804–2817CrossRefGoogle Scholar
  47. 47.
    Atta AM, Shaker NO, Maysour NE (2006) Influence of the molecular structure on the chemical resistivity and thermal stability of cured Schiff base epoxy resins. Prog Org Coat 56:100–110CrossRefGoogle Scholar
  48. 48.
    Hsiao SH, Guo WJ, Lee WF, Kung YC, Lee YJ (2011) Synthesis and characterization of electrochromic poly(amide-imide)s bearing methoxy-substituted triphenylamine units. Mater Chem Phys 130:1086–1093CrossRefGoogle Scholar
  49. 49.
    Cai JW, Ma LN, Niu HJ, Zhao P, Lian YF, Wang W (2013) Near infrared electrochromic naphthalene-based polyimides containing triarylamine: Synthesis and electrochemical properties. Electrochim Acta 112:59–67CrossRefGoogle Scholar
  50. 50.
    Cai JW, Niu HJ, Wang C, Ma LN, Bai XD, Wang W (2012) Tuning the bandgaps of polyazomethines containing triphenylamine by different linkage sites of dialdhyde monomers. Electrochim Acta 76:229–241CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  1. 1.School of Material Science and EngineeringHarbin Institute of TechnologyHarbinPeople’s Republic of China
  2. 2.Key Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Department of Macromolecular Science and Engineering, School of Chemical, Chemical Engineering and MaterialsHeilongjiang UniversityHarbinPeople’s Republic of China

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