Advertisement

Synthesis, characterization and properties of poly(N-allyl-tetrasubstituted imidazole)

  • Haikun Chang
  • Xiaodong Chen
  • Qingyang Hu
  • Yanpeng Shi
  • Ran Zheng
  • Jie Fan
  • Qiang Gu
  • Yumin ZhangEmail author
Original Paper

Abstract

A new poly(N-allyl-tetrasubstituted imidazole) containing furan rings and benzene ring was synthesized starting from 1-allyl-4,5-di(furan-2-yl)-2-phenyl-1H-imidazole (N-allyl-tetrasubstituted imidazole, monomer) using benzoyl peroxide as an initiator coupled with the mixture of benzene and water as solvents. The influence factors on the conversion of N-allyl-tetrasubstituted imidazole (monomer) were optimized by the orthogonal experiment. The structure and property of the obtained monomer and polymers were characterized by Fourier infrared spectroscopy, high-resolution mass spectroscopy, nuclear magnetic resonance spectroscopy, X-ray diffraction, gel permeation chromatography, differential scanning calorimetry and thermogravimetric analysis. Moreover, the luminescence property of monomer and polymers from the different polymerization conditions was investigated. The results showed that the luminescence property and thermal stability of polymer were related to molecular weight and the crystallization degree of polymer, and their thermal stability was markedly better than monomer. It suggested that poly(N-allyl-tetrasubstituted imidazole) had potential application in the fields of heat-resistant material and luminescence material.

Keywords

Poly(N-allyl-tetrasubstituted imidazole) Polymerization Fluorescent polymer Thermal stability 

Notes

Acknowledgements

We are thankful to C. Y. Wang for NMR spectra, Z. L. Wei for Ms spectra and X. D. Chen for XRD.

Supplementary material

289_2019_2680_MOESM1_ESM.doc (486 kb)
Supplementary material 1 (DOC 485 kb)

References

  1. 1.
    Song D, Ma S (2016) Recent development of benzimidazole-containing antibacterial agents. Chem Med Chem 11:646–659CrossRefGoogle Scholar
  2. 2.
    Hohard AH, John AR (1964) 2-p-anilinophenylaminoimidazoline and its salts. US Patent 3146240Google Scholar
  3. 3.
    Erb JDF, Montgomery EL, Ritter ED (2004) Fire blocking fabric. US Patent 6790795Google Scholar
  4. 4.
    Law KY (1993) Organic photoconductive materials: recent trends and developments. Chem Rev 93:449–486CrossRefGoogle Scholar
  5. 5.
    Grazulevicius JV, Strohriegl P, Pielichowski J, Pielichowski K (2003) Carbazole-containing polymers: synthesis, properties and applications. Prog Polym Sci 28:1297–1353CrossRefGoogle Scholar
  6. 6.
    Lee BS, Mahajan S, Janda KD (2005) Cross-linked poly(4-vinylpyridine/styrene) copolymers as a support for immobilization of ytterbium triflate. Cheminform 36:3081–3086Google Scholar
  7. 7.
    Hou Z, Tan Y, Zhou Q (2006) Side-chain pseudopolyrotaxanes by threading cucurbituril onto quaternized poly-4-vinylpyridine derivative: synthesis and properties. Polym 47:5267–5274CrossRefGoogle Scholar
  8. 8.
    Nowakowska M, Zapotoczny S, Karewicz A (2001) Polymeric photosensitizers. Part 4. Synthesis of poly(sodium styrenesulfonate-block-N-vinylcarbazole) by nitroxide-mediated free radical polymerization. Polym 42:1817–1823CrossRefGoogle Scholar
  9. 9.
    Ihm JE, Han KO, Han IK, Ahn KD, Han DK, Cho CS (2003) High transfection efficiency of poly(4-vinylimidazole) as a new gene carrier. Bioconjugate Chem 14:707–708CrossRefGoogle Scholar
  10. 10.
    Ihm JE, Han KO, Hwang CS, Kang JH, Ahn KD, Han IK (2005) Poly (4-vinylimidazole) as nonviral gene carrier: in vitro and in vivo transfection. Acta Biomater 1:165–172CrossRefGoogle Scholar
  11. 11.
    Jayabharathi J, Thanikachalam V, Jayamoorthy K (2012) Photophysical studies of some heterocyclic chromophores as potential NLO materials. Spectrochim Acta, Part A 89:301–307CrossRefGoogle Scholar
  12. 12.
    Anderson EB, Long TE (2010) Imidazole- and imidazolium-containing polymers for biology and material science applications. Polymer 51:2447–2454CrossRefGoogle Scholar
  13. 13.
    Schemeth D, Noël JC, Jakschitz T, Matthias R, Richard T, Christian WH, Günther KB (2015) Poly(N-vinylimidazole/ethylene glycol dimethacrylate) for the purification and isolation of phenolic acids. Anal Chim Acta 885:199–206CrossRefGoogle Scholar
  14. 14.
    Zhao L, Li SB, Wen GA, Peng B, Huang W (2006) Imidazole derivatives: thermally stable organic luminescence materials. Mater Chem Phys 100:460–463CrossRefGoogle Scholar
  15. 15.
    Fang ZJ, Wang SM, Zhao L, Xu ZX, Ren J, Wang XB, Yang QF (2007) A novel polymerizable imidazole derivative for blue light-emitting material. Mater Lett 61:4803–4806CrossRefGoogle Scholar
  16. 16.
    Huang J, Su JH, Tian H (2012) The development of anthracene derivatives for organic light-emitting diodes. J Mater Chem 22:10977–10989CrossRefGoogle Scholar
  17. 17.
    Li BZ, Gu Q, Kang J, Zhang YM (2012) Facile synthesis of trisubstituted imidazoles from 1,2-di(furan-2-yl)-2-oxoethyl carboxylates and their chemiluminescence. C R Chim 15:784–792CrossRefGoogle Scholar
  18. 18.
    Liao Q, Nie Z, Chen H, Luo X, Gao Y, Li H (2012) Unique UV absorbance for triphenylimidazole-based polymer. J Appl Polym Sci 126:1146–1151CrossRefGoogle Scholar
  19. 19.
    Green MD, Allen MH Jr, Dennis JM, Cruz DSDL, Gao RG, Winey KI, Long TE (2011) Tailoring macromolecular architecture with imidazole functionality: a perspective for controlled polymerization processes. Eur Polym J 47:486–496CrossRefGoogle Scholar
  20. 20.
    Kuznetsov VA, Lavlinskaya MS, Ostankova IV, Shatalov GV, Shikhaliev KS, Ryzhkova EA (2018) Synthesis of N-vinylformamide and 1-vinyl-(1methacryloyl)-3,5-dimethylpyrazole copolymers and their extraction ability in relation to histidine in water-salt media. Polym Bull 75:1237–1251CrossRefGoogle Scholar
  21. 21.
    Ge ZS, Xie D, Chen DY, Jiang XZ, Zhang YF, Liu HW, Liu SY (2007) Stimuli-responsive double hydrophilic block copolymer micelles with switchable catalytic activity. Macromolecules 40:3538–3546CrossRefGoogle Scholar
  22. 22.
    Stancik CM, Lavoie AR, Schutz J, Achurra PA, Lindner P, Gast AP, Waymouth RM (2004) Micelles of imidazolium-functionalized polystyrene diblock copolymers investigated with neutron and light scattering. Langmuir 20:596–605CrossRefGoogle Scholar
  23. 23.
    Stancik CM, Lavote AR, Achurra PA, Waymouth RM, Gast AP (2004) A neutron scattering study of the structure and water partitioning of selectively deuterated copolymer micelles. Langmuir 20:8975–8987CrossRefGoogle Scholar
  24. 24.
    Lawson KJ (2002) 2-Vinylimidazole and 1-methyl-2-vinylimidazole. J Am Chem Soc 75:3398–3400CrossRefGoogle Scholar
  25. 25.
    Odian G (2004) Principles of polymerization, Chapter 5. Wiley, Hoboken, p 679CrossRefGoogle Scholar
  26. 26.
    Gill JE (1969) The fluorescence excitation spectrum of quinine bisulfate. Photochem Photobiol 9:313–322CrossRefGoogle Scholar
  27. 27.
    Yuan CG, Zhu YZ (2012) Modern instrumental analysis. Chemical Industry Press, Beijing, p p19Google Scholar
  28. 28.
    Ci YX, Jia X (1986) Determination of relative fluorescence quantum yields using simplified method. Chin J Anal Chem 58:616–618CrossRefGoogle Scholar
  29. 29.
    Chen Y, Gu Q, Li B, Chen Q, Chen XD, Zhang YM, Liu JX (2013) Efficient synthesis of 1-R1-2-R-4,5-di(furan-2-yl)-1H-imidazoles and their luminescence properties. C R Chim 16:1103–1110CrossRefGoogle Scholar
  30. 30.
    Jangu C, Schultz AR, Wall CE, Esker AR, Long TE (2016) Diphenylphosphino styrene-containing homopolymers: influence of alkylation and mobile anions on physical properties. Macromol Rapid Commun 37:1212–1217CrossRefGoogle Scholar
  31. 31.
    Iwamura T, Sakaguchi M (2008) A novel de-cross-linking system from cross-linked polymer to linear polymer utilizing pressure or visible light irradiation. Macromolecules 41(23):8995–8999CrossRefGoogle Scholar
  32. 32.
    Lu YB, Shang YB, Huang X, Chen AM, Yang Z et al (2011) Preparation of strong cationic chitosan-graft-polyacrylamide flocculants and their flocculating properties. Ind Eng Chem Res 50:7141–7149CrossRefGoogle Scholar
  33. 33.
    Ge H, Pang W, Luo D (2006) Graft copolymerization of chitosan with acrylic acid under microwave irradiation and its water absorbency. Carbohydr Polym 66:372–378CrossRefGoogle Scholar
  34. 34.
    Guha S, Ray B, Mandal BM (2001) Anomalous solubility of polyacrylamide prepared by dispersion (precipitation) polymerization in aqueous tert-butyl alcohol. J Polym Sci, Part A: Polym Chem 39:3434–3442CrossRefGoogle Scholar
  35. 35.
    Paine AJ, Luymes W, Nulty JM (1990) Dispersion polymerization of styrene in polar solvents. 6. Influence of reaction parameters on particle size and molecular weight in poly(N-vinylpyrrolidone)-stabilized reactions. Macromolecules 23:3104–3109CrossRefGoogle Scholar
  36. 36.
    Guan Q, Zheng H, Zhai H, Zhao C, Zheng X, Tang X, Chen W, Sun Y (2014) Effect of template on structure and properties of cationic polyacrylamide: characterization and mechanism. Ind Eng Chem Res 53:5624–5635CrossRefGoogle Scholar
  37. 37.
    Guo JS, Sudol ED, Vanderhoff JW, ELAasser MS (1992) Particle nucleation and monomer partitioning in styrene O/W microemulsion polymerization. J Polym Sci Part A Polym Chem 30:691–702CrossRefGoogle Scholar
  38. 38.
    Johnson PL, Gulari E (1984) Characteristics of microemulsion polymerized styrene with water-soluble versus oil-soluble initiators. J Polym Sci Polym Chem Ed 22:3967–3982CrossRefGoogle Scholar
  39. 39.
    Perez-Luna VH, Puig JE, Castano VM, Rodriguez BE, Murthy AK, Kaler EW (1990) Styrene polymerization in three-component cationic microemulsions. Langmuir 6:1040–1044CrossRefGoogle Scholar
  40. 40.
    Hou Y, Zhao T, Shi Y, Fan J, Zheng R, Zhang Y, Gu Q (2018) Surface modification of carbon black for facilitating the suspension polymerization of styrene and carbon black. J Appl Polym Sci.  https://doi.org/10.1002/app.46387 Google Scholar
  41. 41.
    Sarala L, Yathirajula RB, Gopikrishna P, Elaiyappillai E, Bella A, Manoharan SS, Iyer PK, Johnson PM (2018) Pronounced luminescence efficiency and thermal stability of small imidazole architect 2-(1, 4, 5-triphenyl-1H-imidazol-2-yl)phenol for efficient non-doped blue OLEDs. J Photochem Photobiol A Chem 365:232–237CrossRefGoogle Scholar
  42. 42.
    Chen GZ, Huang ZX, Zheng ZZ (1990) Fluorescence analysis. Science Press, Beijing, p 10Google Scholar
  43. 43.
    Fletcher AN (1967) Fluorescence emission band shift with wavelength of excitation. J Phys Chem 72:2742–2749CrossRefGoogle Scholar
  44. 44.
    Zhang GQ, Kooi SE, Demas JN, Fraser CL (2010) Emission color tuning with polymer molecular weight for difluoroboron dibenzoylmethane-polylactide. Adv Mater 20:2099–2104CrossRefGoogle Scholar
  45. 45.
    Loutfy RO (1986) Fluorescence probes for polymer free-volume. Pure Appl Chem 58:1239–1248CrossRefGoogle Scholar
  46. 46.
    Jayabharathi J, Thanikachalam V, Srinivasan N, Perumal MV (2012) Fluorescence spectral studies of some imidazole derivatives. Spectrochim Acta, Part A 90:125–130CrossRefGoogle Scholar
  47. 47.
    Wang JS, Gu Q, Su Q, Chen XD, Zhang YM (2009) 2,4,5-Tri-furan-2-yl-1H-imidazole. Acta Crystallogr Sect E: Struct Rep Online 65:3194CrossRefGoogle Scholar
  48. 48.
    Carraway ER, Demas JN, Degraff BA, Bacon JR (1991) Photophysics and photochemistry of oxygen sensors based on luminescent transition-metal complexes. Anal Chem 63:337–342CrossRefGoogle Scholar
  49. 49.
    Zhang G, Clair TLS, Fraser CL (2009) Synthesis and fluorescent properties of difluoroboron dibenzoylmethane polycaprolactone. Macromolecules 42:3092–3097CrossRefGoogle Scholar
  50. 50.
    Vetrova EV, Makarova NI, Omelichkin NI, Minyaeva LG, Chernyavinab VV, Borisenkoc RN, Metelitsa AV (2019) Insights into the solvents effect on spectral and photophysical properties of novel fluorescent heteroaromatic bis-peri-fused azoxonium cations. J Photochem Photobiol A Chem 370:127–134CrossRefGoogle Scholar
  51. 51.
    Zeng HP, Wang GR, Zeng GC, Li J (2009) The synthesis, characterization and electroluminescent properties of zinc (II) complexes for single-layer organic light-emitting diodes. Dyes Pigm 83:155–161CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Haikun Chang
    • 1
  • Xiaodong Chen
    • 1
  • Qingyang Hu
    • 2
  • Yanpeng Shi
    • 1
  • Ran Zheng
    • 1
  • Jie Fan
    • 1
  • Qiang Gu
    • 1
  • Yumin Zhang
    • 1
    Email author
  1. 1.College of ChemistryJilin UniversityChangchunPeople’s Republic of China
  2. 2.Shandong Gold Mining(Laizhou) Co. Ltd.ShandongPeople’s Republic of China

Personalised recommendations