Skip to main content
Log in

New cyano-substituted copolymers containing biphenylenevinylene and bithienylenevinylene units: synthesis, optical, and electrochemical properties

  • Published:
Journal of Materials Science Aims and scope Submit manuscript

Abstract

Two new cyano-substituted copolymers containing biphenylenevinylene and bithienylenevinylene moieties (DCN-PPV and DCN-PTV) were synthesized by a stille condensation reaction with Pd(PPh3)4 as catalyst. Their structures were confirmed by 1H NMR, IR spectroscopy, and elemental analysis. The thermal, optical, and electrochemical properties of the polymers were investigated. The results show that the polymers possess high thermal decomposition temperature and reversible n-doping/dedoping processes. In addition, DCN-PTV has higher electron affinity with a low LUMO energy level of −3.84 eV and a relatively broader absorption band covering 300–780 nm, indicating that DCN-PTV could be a potential n-type conjugated polymer in optoelectronic devices.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Shirakawa H, Louis EL, MacDiarmid AG, Chiang CK, Heeger AJ (1977) J Chem Soc Chem Commun 578

  2. Martijn MW, Mathieu GRT, Martin PS, Marta F, René AJJ (2006) Appl Phys Lett 88:153511

    Article  Google Scholar 

  3. Hou JH, Fan BH, Huo LJ, He C, Yang CH, Li YF (2006) J Polym Sci Part A: Polym Chem 44:1279

    Article  CAS  Google Scholar 

  4. Wu TY, Chen Y (2002) J Polym Sci Part A: Polym Chem 40:3847

    Article  CAS  Google Scholar 

  5. Wang WZ, Zhu R, Fan QL, Xu H, Hou LT, Cao Y, Huang W (2006) Macromol Rapid Commun 27:1142

    Article  CAS  Google Scholar 

  6. Huang J, Xu YS, Hou Q, Yang W, Yuan M, Cao Y (2002) Macromol Rapid Commun 23:709

    Article  CAS  Google Scholar 

  7. Zou YP, Tan ST, Yuan ZL, Yu ZQ (2005) J Mater Sci 40:3561. doi:10.1007/s10853-005-2878-7

    Article  ADS  CAS  Google Scholar 

  8. Tan ST, Zou YP, Zhu WG, Jiang CY (2006) Opt Mater 28:1108

    Article  ADS  CAS  Google Scholar 

  9. Zou YP, Tan ST, Yuan ZL, YU ZQ (2005) J Mater Sci 40:3569. doi:10.1007/s10853-005-2889-4

    Article  ADS  CAS  Google Scholar 

  10. Shi CJ, Yao Y, Yang Y, Pei QB (2006) J Am Chem Soc 128:8980

    Article  PubMed  CAS  Google Scholar 

  11. Ashraf RS, Shahid M, Klemm E, Al-Ibrahim M, Sensfuss S (2006) Macromol Rapid Commun 27:1454

    Article  CAS  Google Scholar 

  12. Zhou EJ, Tan Z, Yang CH, Li YF (2006) Macromol Rapid Commun 27:793

    Article  CAS  Google Scholar 

  13. Marin V, Holder E, Wienk MM, Tekin E, Kozodaev D, Schubert US (2005) Macromol Rapid Commun 26:319

    Article  CAS  Google Scholar 

  14. Blouin N, Michaud A, Leclerc M (2007) Adv Mater 19:2295

    Article  CAS  Google Scholar 

  15. Zou YP, Gendron D, Alch RB, Najari A, Tao Y, Leclerc M (2009) Macromolecules 42:2891

    Article  CAS  Google Scholar 

  16. Bäuerle P, Emge A (1998) Adv Mater 3:324

    Article  Google Scholar 

  17. Shkunov M, Simms R, Heeney M, Tierney S, McCulloch I (2005) Adv Mater 17:2608

    Article  CAS  Google Scholar 

  18. Cheng F, Zhang GW, Lu XM, Huang YQ, Chen Y, Zhou Y, Fan QL, Huang W (2006) Macromol Rapid Commun 27:799

    Article  CAS  Google Scholar 

  19. Zou YP, Wan MX, Sang GY, Ye MF, Li YF (2008) Adv Funct Mater 18:2724

    Article  CAS  Google Scholar 

  20. Hou JH, Tan Z, Yan Y, He Y, Yang CH, Li YF (2006) J Am Chem Soc 128:4911

    Article  PubMed  CAS  Google Scholar 

  21. Wienk MM, Kroon JM, Verhees WJH, Knol J, Hummelen JC, Hal PAV, Janssen RAJ (2003) Angew Chem Int Ed 42:3371

    Article  CAS  Google Scholar 

  22. Shaheen SE, Brabec CJ, Sariciftci NS, Padinger F, Fromherz T, Hummelen JC (2001) Appl Phys Lett 78:841

    Article  ADS  CAS  Google Scholar 

  23. Yu G, Heeger AJ (1995) J Appl Phys 78:4510

    Article  ADS  CAS  Google Scholar 

  24. Halls JJM, Walsh CA, Greenham NC, Marseglia EA, Friend RH, Moratti SC, Holmes AB (1995) Nature 376:498

    Article  ADS  CAS  Google Scholar 

  25. Veenstra SC, Verhees WJH, Kroon JM, Koetse MM, Sweelssen J, Bastiaansen JJAM, Schoo HFM, Yang X, Alexeev A, Loos J, Schubert US, Wienk MM (2004) Chem Mater 16:2503

    Article  CAS  Google Scholar 

  26. Yamamoto T, Lee BL, Kokubo H, Kishida H, Hirota K, Wakabayashi T, Okamoto H (2003) Macromol Rapid Commun 7:24

    Google Scholar 

  27. Hou JH, Huo LJ, He C, Yang CH, Li YF (2006) Macromolecules 39:594

    Article  ADS  CAS  Google Scholar 

  28. Zhou EJ, Hou JH, Yang CH, Li YF (2006) J Polym Sci Part A: Polym Chem 44:2206

    Article  CAS  Google Scholar 

  29. Granstro¨m M, Petritsch K, Arias AC, Lux A, Andersson MR, Friend RH (1998) Nature 395:257

    Article  ADS  Google Scholar 

  30. Kietzke T, Ho¨rhold HH, Neher D (2005) Chem Mater 17:6532

    Article  CAS  Google Scholar 

  31. Zou YP, Hou JH, Yang CH, Li YF (2006) Macromolecules 39:8889

    Article  ADS  CAS  Google Scholar 

  32. Cho NS, Hwang DH, Jung BJ, Lim E, Lee J, Shim HK (2004) Macromolecules 37:5265

    Article  ADS  CAS  Google Scholar 

  33. Chen Z, Meng H, Lai Y, Huang W (1999) Macromolecules 32:4351

    Article  ADS  CAS  Google Scholar 

  34. Hou JH, Tan Z, He Y, Yang CH, Li YF (2006) Macromolecules 39:4657

    Article  ADS  CAS  Google Scholar 

  35. Li YF, Cao Y, Gao J, Wang DL, Yu G, Heeger AJ (1999) Synth Met 99:243

    Article  CAS  Google Scholar 

  36. Sun QJ, Wang HQ, Yang CH, Li YF (2003) J Mater Chem 13:800

    Article  CAS  Google Scholar 

  37. Yamamoto T, Komarudin D, Arai M, Lee B-L, Suganuma H, Asakawa N, Inoue Y, Kubota K, Sasaki S, Fukuda T, Matsuda H (1998) J Am Chem Soc 120:2047

    Article  CAS  Google Scholar 

  38. Babel A, Jenekhe SA (2003) J Am Chem Soc 125:13656

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by National Natural science Foundation of China (Nos. 50803074 and 50633050), the Opening Fund of State Key Laboratory of Powder Metallurgy, and Start-up fund of Central South University.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yingping Zou.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zou, Y., Liu, B., Li, Y. et al. New cyano-substituted copolymers containing biphenylenevinylene and bithienylenevinylene units: synthesis, optical, and electrochemical properties. J Mater Sci 44, 4174–4180 (2009). https://doi.org/10.1007/s10853-009-3622-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10853-009-3622-5

Keywords

Navigation