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Journal of Materials Science

, Volume 44, Issue 12, pp 3172–3178 | Cite as

Preparation and properties of alternating 2,7-linked carbazole copolymers with phenylene units with varying number of fluorine substituents

  • David F. Pickup
  • Hunan Yi
  • Ahmed IraqiEmail author
Article
First Online:

Abstract

New alternating copolymers comprising 2,7-linked-3,6-dimethyl-9-(2-hexyldecy)-9H-carbazole and 1,4-phenylene units (P1), 2,5-difluoro-1,4-phenylene units (P2), and 2,3,5,6-tetrafluoro-1,4-phenylene units (P3) have been prepared using Suzuki cross-coupling conditions. The polymers were characterized by NMR spectroscopy, UV–vis absorption spectroscopy, fluorescence spectroscopy, and their weight-average molecular weights were estimated using gel permeation chromatography. The polymers are thermally stable up to 420 °C and display wide band gaps ranging from 3.16 to 3.2 eV. The polymers are electrolytically stable and emit around 400 nm. A discussion on the effect of the varying degree of fluorine substitution of the phenylene repeat units in polymers P1–P3 on their physical properties is presented.

Keywords

Repeat Unit Carbazole Phenylboronic Acid Aromatic Region Tetrabutylammonium Perchlorate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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Notes

Acknowledgement

We would like to acknowledge EPSRC (Grant number GR/S56719/01) for financial support of this work.

References

  1. 1.
    Virgili T, Lidzey DG, Bradley DDC (2000) Adv Mater 12:58CrossRefGoogle Scholar
  2. 2.
    Liang B, Jiang C, Chen Z, Zhang X, Shi H, Cao Y (2006) J Mater Chem 16:1281CrossRefGoogle Scholar
  3. 3.
    Zhang X, Chen Z, Yang C, Li Z, Zhang K, Yao H, Qin J, Chen J, Cao Y (2006) Chem Phys Lett 422:386CrossRefGoogle Scholar
  4. 4.
    Cleave V, Yahioglu G, Le Barny P, Hwang D-H, Holmes AB, Friend RH, Tessler N (2001) Adv Mater 13:44CrossRefGoogle Scholar
  5. 5.
    O’Brien DF, Giebeler C, Fletcher RB, Cadby AJ, Palilis LC, Lidzey DG, Lane PA, Bradley DDC, Blau W (2001) Synth Met 116:379CrossRefGoogle Scholar
  6. 6.
    Guo T-F, Chang S-C, Yang Y, Kwong RC, Thompson ME (2000) Org Electron 1:15CrossRefGoogle Scholar
  7. 7.
    Jiang C, Yang W, Peng J, Xiao S, Cao Y (2004) Adv Mater 16:537CrossRefGoogle Scholar
  8. 8.
    Hong H, Sfez R, Yitzchaik S, Davidov D (1999) Synth Met 102:1217CrossRefGoogle Scholar
  9. 9.
    Lamansky S, Kwong RC, Nugent M, Djurovich PI, Thompson ME (2001) Org Electron 2:53CrossRefGoogle Scholar
  10. 10.
    Zeng G, Yu W-L, Chua S-J, Huang W (2002) Macromolecules 35:6907CrossRefGoogle Scholar
  11. 11.
    List EJW, Guentner R, de Scanducci de FP, Scherf U (2002) Adv Mater 14:374CrossRefGoogle Scholar
  12. 12.
    Becker K, Lupton JM, Feldmann J, Nehls BS, Galbrecht F, Gao D, Scherf U (2006) Adv Funct Mater 16:364CrossRefGoogle Scholar
  13. 13.
    Zotti G, Schiavon G, Zecchin S, Morin J-F, Leclerc M (2002) Macromolecules 35:2122CrossRefGoogle Scholar
  14. 14.
    Iraqi A, Wataru I (2004) Chem Mater 16:442CrossRefGoogle Scholar
  15. 15.
    Yi H, Iraqi A, Stevenson M, Elliott CJ, Lidzey DG (2007) Macromol Rapid Commun 28:1155CrossRefGoogle Scholar
  16. 16.
    Iraqi A, Pickup DF, Yi H (2006) Chem Mater 18:1007CrossRefGoogle Scholar
  17. 17.
    Krebs FC, Jorgensen M (2003) Polym Bull 51:127CrossRefGoogle Scholar
  18. 18.
    Crouch DJ, Skabara PJ, Lohr JE, McDouall JJW, Heeney M, McCulloch I, Sparrowe D, Shkunov M, Coles SJ, Horton PN, Hursthouse MB (2005) Chem Mater 17:6567CrossRefGoogle Scholar
  19. 19.
    Assaka AM, Rodrigues PC, De Oliveira ARM, Ding L, Hu B, Karasz FE, Akcelrud L (2004) Polymer 45:7071CrossRefGoogle Scholar
  20. 20.
    Kameshima H, Nemoto N, Endo T (2001) J Polym Sci Part A: Polym Chem 39:3143CrossRefGoogle Scholar
  21. 21.
    Gritzner G (1990) Pure Appl Chem 62:1839CrossRefGoogle Scholar
  22. 22.
    Iraqi A, Wataru I (2004) J Polym Sci Part A: Polym Chem 42:6041CrossRefGoogle Scholar
  23. 23.
    Kulasi A, Yi H, Iraqi A (2007) J Polym Sci Part A: Polym Chem 45:5957CrossRefGoogle Scholar
  24. 24.
    Pommerehne J, Vestweber H, Guss W, Mahrt RF, Bässler H, Porsch M, Daub J (1995) Adv Mater 7:551CrossRefGoogle Scholar
  25. 25.
    Janietz S, Bradley DDC, Grell M, Giebeler C, Inbasekaran M, Woo EP (1998) Appl Phys Lett 73:2453CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of SheffieldSheffieldUK

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