Skip to main content
SpringerLink
Log in

Electrosynthesis of thin films of polythiophenes containing pyrene groups and flexible spacers, useful in the preparation of graphene polymer composites

  • Articles
  • Published:
MRS Advances Aims and scope Submit manuscript

Abstract

Thin polythiophene films were prepared by electrodeposition, using two novel thiophene monomers containing a pyrene unit linked via a flexible spacer. The obtained polymers have a suitable architecture for the further preparation of polymer composites with graphene via π-π interactions. Physicochemical characterization of the precursor polymers demonstrated that the resulting films are made of homogeneous electroactive polythiophene with pendant pyrene units regularly located on the polymer surface. These compounds are highly emissive and easily form excimers as other high pyrene content polymers. The polymer emission can be drastically quenched by the interaction with graphene after dipping the film into an aqueous suspension of reduced graphite oxide. The presence of aggregated graphene onto pyrene rich content areas by non-covalent interactions has been confirmed by AFM analysis. This kind of polythiophene/pyrene thin films showed to be a good matrix for the elaboration of fluorescent polymer composites.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A.K. Geim, K.S. Novoselov, Nat. Mater. 6 (2007) 183–191.

    Article  CAS  Google Scholar 

  2. K.S. Novoselov, A.K Geim, S.V. Morozov, D. Jiang, Y. Zhang, S.V. Dubonos, I.V. Grigorieva, A.A. Firsov, Science 306 (2004) 666–669.

    CAS  Google Scholar 

  3. Y. Xu, Y. Wang, J. Liang, Y. Huang, Y. Ma, X. Wan, Y. Chen, Nano Res. 2 (2009) 343–348.

    Article  CAS  Google Scholar 

  4. Z. Yang, X. Shi, J. Yuan, H. Pu, Y. Liu, Appl. Surf. Sci. 257 (2010) 138–142.

    Article  CAS  Google Scholar 

  5. X. Wang, J. Wang, H. Cheng, P. Yu, J. Ye, L. Mao, Langmuir 27 (2011) 11180–11186.

    Article  CAS  Google Scholar 

  6. F. Li, J. Song, H. Yang, S. Gan, Q. Zhang, D. Han, A. Ivaska, L. Niu, Nanotechnology 20 (2009) 455602.

    Article  CAS  Google Scholar 

  7. W. Tu, J. Lei, S. Zhang, H. Ju, Chem. Eur. J. 16 (2010) 10771–10777.

    Article  CAS  Google Scholar 

  8. G. Zeng, Y. Xing, J. Gao, Z. Wang, X. Zhang, Langmuir 26 (2010) 15022–15026.

    Article  CAS  Google Scholar 

  9. W. Hong, H. Bai, Y. Xu, Z. Yao, Z. Gu, G. Shi, J. Phys. Chem. C 114 (2010) 1822–1826.

    Article  CAS  Google Scholar 

  10. D.A. Dikin, S. Stankovich, E.J. Zimney, R.D. Piner, G.H.B. Dommett, G. Evmenenko, S.T. Nguyen, R.S. Ruoff, Nature 448 (2007) 457–460.

    Article  CAS  Google Scholar 

  11. C. Berger, Z. Song, X. Li, X. Wu, N. Brown, C. Naud, D. Mayou, T. Li, J. Hass, A.N. Marchenkov, E.H. Conrad, P.N. First, W.A. de Heer, Science 312 (2006) 1191–1196.

    Article  CAS  Google Scholar 

  12. D. Wei, Y. Liu, Y. Wang, H. Zhang, L. Huang, G. Yu, Nano Lett. 9 (2009) 1752–1758.

    Article  CAS  Google Scholar 

  13. H. Chen, M.B. Muller, K.J. Gilmore, G.G. Wallace, D. Li, Adv. Mater. 20 (2008) 3557–3561.

    Article  CAS  Google Scholar 

  14. X.L. Li, X.R. Wang, L. Zhang, S.W Lee, H.J Dai, Science 319 (2008) 1229–1232.

    Article  CAS  Google Scholar 

  15. X. Li, G. Zhang X. Bai, X. Sun, X. Wang, E. Wang, H. Dai, Nat. Nanotechnol. 3 (2008) 538–542.

    Article  CAS  Google Scholar 

  16. M. Choucair, P. Thordarson, J.A. Stride, Nat. Nanotechnol. 4 (2009) 30–33.

    Article  CAS  Google Scholar 

  17. B. Das, R. Voggu, C.S. Rout, C.N.R. Rao, Chem. Commun., 41 (2008), 5155–5157.

    Article  CAS  Google Scholar 

  18. R. Voggu, B. Das, C.S. Rout, C.N.R. Rao, J. Phys.: Condens. Matter 20 (2008) 472204 (1–5).

    Google Scholar 

  19. K.S. Subrahmanyam, R. Voggu, A. Govindaraj, C.N.R. Rao, Chem. Phys. Lett. 472 (2009) 96–98.

    Article  CAS  Google Scholar 

  20. K.S. Subrahmanyam, A. Ghosh, A. Gomathi, A. Govindaraj, C.N.R. Rao, Nanosci. Nanotechnol. Lett. 1 (2009) 28–31.

    Article  CAS  Google Scholar 

  21. A. Ghosh, K.V. Rao, S.J. George, C.N.R. Rao, Chem. Eur. J. 16 (2010) 2700–2704.

    Article  CAS  Google Scholar 

  22. S. Stepanian, V.A. Karachevtsev, A.Y. Glamazda, U. Dettlaff-Weglikowska, L. Mol. Phys. 101 (2003) 2609–2614.

    Article  CAS  Google Scholar 

  23. Y.H. Xie, A.K Soh, Mater. Lett. 59 (2005) 971–975.

    Article  CAS  Google Scholar 

  24. J.A.A.W. Elemans, R. Van Hameren, R.J.M. Nolte, A.E Rowan, Adv. Mater. 18 (2006) 1251–1266.

    Article  CAS  Google Scholar 

  25. D.M. Guldi, G.M.A. Rahman, F. Zerbetto, M. Prato, Acc. Chem. Res. 38 (2005) 871–878.

    Article  CAS  Google Scholar 

  26. H. Murakami, T. Nomura, N. Nakashima, Chem. Phys. Lett. 378 (2003) 481–485.

    Article  CAS  Google Scholar 

  27. M. Alvaro, C. Aprile, B. Ferrer, H. Garcia, J. Am. Chem. Soc. 129 (2007) 5647–5655.

    Article  CAS  Google Scholar 

  28. D.M. Guldi, A. Rahman, V. Sgobba, C. Ehli, Chem. Soc. Rev. 35 (2006) 471–487.

    Article  CAS  Google Scholar 

  29. R. Martin, M. Alvaro, H. Garcia, Curr. Org. Chem. 15 (2011) 1106–1120.

    Article  CAS  Google Scholar 

  30. I. Robel, B.A. Bunker, P.V. Kamat, Adv. Mater. 17 (2005) 2458–2463.

    Article  CAS  Google Scholar 

  31. M. De Miguel, M. Álvaro, H. García, Langmuir 28 (2012) 2849–2857.

    Article  CAS  Google Scholar 

  32. Y. Xu, Z. Liu, X. Zhang, Y. Wang, J. Tian, Y. Huang, Y. Ma, X. Zhang, Y. Chen, Adv. Mater. 21 (2009) 1275–1279.

    Article  CAS  Google Scholar 

  33. Y. Xu, L. Zhao, W. Hong, C. Li, G. Shi, J. Am. Chem. Soc. 131 (2009) 13490–13497.

    Article  CAS  Google Scholar 

  34. R.S. Swathi, K.L. Sebastian, J. Chem. Phys 129 (2008) 054703.

    Article  CAS  Google Scholar 

  35. R.S. Swathi, K.L. Sebastian, J. Chem Phys 130 (2009) 086101.

    Article  CAS  Google Scholar 

  36. CH. Lu, H.H. Yang, CL. Zhu, X. Chen, G.N. Chen, Angew. Chem. Int Ed. 48 (2009) 4785–4787.

    Article  CAS  Google Scholar 

  37. E. Treossi, M. Melucci, A. Liscio, M. Gazzano, P. Samori, V. Palermo, J. Am. Chem. Soc. 131 (2009) 15576–15577.

    Article  CAS  Google Scholar 

  38. P.V. Kamat, J. Phys. Chem. Lett. 1 (2010) 520–527.

    Article  CAS  Google Scholar 

  39. L. Xie, X. Ling, Y. Fang, J. Zhang, Z. Liu, J. Am. Chem. Soc. 131 (2009) 9980–9981.

    Google Scholar 

  40. Y. Liu, C.Y. Liu, Appl. Surf. Sci. 257 (2010) 5513–5518.

    Article  CAS  Google Scholar 

  41. H. Matte, K.S. Subrahmanyam, K.V. Rao, S.J. George, C.N.R. Rao, Chem. Phys. Lett. 506 (2011) 260–264.

    Article  CAS  Google Scholar 

  42. C.N.R. Rao, K.S. Subrahmanyam, H. Matte, A. Govindaraj, Mod. Phys. Lett. B 25 (2010) 427–451.

    Article  CAS  Google Scholar 

  43. J.Q. Tian, H.L. Li, Y.L. Luo, L. Wang, Y.W. Zhang, Y. W., X.P. Sun, Langmuir 27 (2010) 874–877.

    Article  CAS  Google Scholar 

  44. Y.B. Wang, D. Kurunthu, G.W. Scott, C.J. Bardeen, J. Phys. Chem. C 114 (2010) 4153–4159.

    Article  CAS  Google Scholar 

  45. X.M. Wu, H.Q. Cao, B.J. Li, G. Yin, Nanotechnology 22 (2011) 75202.

    Article  CAS  Google Scholar 

  46. X.F. Zhang, Q. Xi, Carbon 49 (2011) 3842–3850.

    Article  CAS  Google Scholar 

  47. F.M. Winnik, Chem. Rev. 93 (1993) 587–614.

    Article  CAS  Google Scholar 

  48. E. Rivera, M. Belletête, X.X. Zhu, G. Durocher, R. Giasson, Polymer 43 (2002) 5059–5068.

    Article  CAS  Google Scholar 

  49. E. Rivera, R. Wang, X.X. Zhu, D. Zargarian, R. Giasson, J. Mol. Catal. 204 (2003) 325–332.

    Article  CAS  Google Scholar 

  50. M. Belletête, E. Rivera, R. Giasson, X.X. Zhu, G. Durocher, Synth. Met. 14 (2004) 37–42.

    Article  CAS  Google Scholar 

  51. O. Morales-Saavedra, E. Rivera, Polymer 47 (2006) 5330–5337.

    Article  CAS  Google Scholar 

  52. K. Yoshino, S. Nakajima, M. Onada, R. Sugimoto, Synth. Met. 28 (1989) 349–357.

    Article  Google Scholar 

  53. B.X. Valderrama-García, K.I Moineau-Chane Ching, E. Rivera, Molecules 21 (2016) 172.

    Article  CAS  Google Scholar 

  54. W.S. Hummers, R.E. Offeman, J. Am. Chem. Soc. 80 (1958) 1339–1339.

    Article  CAS  Google Scholar 

  55. S. Park, J. An, J.R. Potts, A. Velamakanni, S. Murali, R.S. Carbon. 49 (2011) 3019–3023.

    Article  CAS  Google Scholar 

  56. R. Berridge, S.P. Wright, P.J. Skabara, A. Dyer, T. Steckler, A.A. Argun, J.R. Reynolds, R. Harrington, W. Clegg, J. Mater. Chem. 17 (2007) 225–231.

    Article  CAS  Google Scholar 

  57. S. P. Rittmeyel, A. Groß, Beilstein J Nanotechnol. 3 (2012) 909–919.

    Article  CAS  Google Scholar 

  58. Y.X. Yuan, H.S. Peng, J.T. Ping, X.H. Wang, F.T. You, Biomed Res Int 11 (2015) 245031.

    Google Scholar 

  59. P. Beyazkilic, A. Yildirim, M. Bayindir, Nanoscale 6 (2014) 15203–9.

    Article  CAS  Google Scholar 

  60. X. Sun, Y. Liu, G. Shaw, A. Carrier, S. Dey, J. Zhao, Y. Lei, ACS Appl. Mater. Interfaces 7 (2015) 13189–97.

    Article  CAS  Google Scholar 

  61. S. J. Park, S. Kim, T.F. Florence Anjong, S.E. Lee, J. Kim, Carbon 94 (2015) 448–454.

    Article  CAS  Google Scholar 

  62. K. Dimitrios, M.M. Stylianakis, E. Stratakis, E. Kymakis, J. Colloid Interface Sci. 430 (2014), 430, 108–112.

    Google Scholar 

  63. S.M. Rojas-Montoya, M. Vonlanthen, P. Porcu, G. Flores-Rojas, A. Ruiu, D. Morales-Morales, E. Rivera. Dalton Transactions 48 (2019), 10435–10447.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior Ciudad Universitaria, C.P. 0451, Ciudad de México, México

    Bianca X. Valderrama-García, Israel González-Méndez & Ernesto Rivera

  2. LCC (Laboratoire de Chimie de Coordination), CNRS, 205, route de Narbonne, 31077, Toulouse, France

    Bianca X. Valderrama-García, Alix Sournia-Saquet, Marine Tasse & Kathleen I. Moineau-Chane Ching

  3. UPS, INP; LCC, Université de Toulouse, 31077, Toulouse, France

    Alix Sournia-Saquet, Marine Tasse & Kathleen I. Moineau-Chane Ching

Authors
  1. Bianca X. Valderrama-García
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Israel González-Méndez
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alix Sournia-Saquet
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Marine Tasse
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Kathleen I. Moineau-Chane Ching
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ernesto Rivera
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Kathleen I. Moineau-Chane Ching or Ernesto Rivera.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Valderrama-García, B.X., González-Méndez, I., Sournia-Saquet, A. et al. Electrosynthesis of thin films of polythiophenes containing pyrene groups and flexible spacers, useful in the preparation of graphene polymer composites. MRS Advances 4, 3233–3242 (2019). https://doi.org/10.1557/adv.2019.410

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1557/adv.2019.410

Search

Navigation