Journal of Materials Science

, Volume 45, Issue 2, pp 435–442 | Cite as

Stilbene-based liquid crystalline and photocrosslinkable polynaphthylphosphate esters

  • A. Ravikrishnan
  • P. Sudhakara
  • P. KannanEmail author


A series of liquid crystalline and photocrosslinkable polymers were synthesized from 4,4′-bis(m-hydroxyalkyloxy)stilbene (m = 2, 4, 6, 8, 10) with naphthylphosphorodichloridate. The synthesized polymers were characterized by spectroscopic techniques. Thermogravimetric analysis revealed that the polymers were stable between 283 and 341 °C, then underwent two-stage decomposition, and char yield increased with decreasing spacer length. DSC and HOPM analysis disclosed that the polymers IIIV (m = 6, 8, 10) exhibited LC phases wherein flexible methylene spacer separates mesogenic alignment and reduces overall rigidity of polymers, while polymers I and II are unable to show LC phase. The photolysis was studied by UV–visible and fluorescence spectroscopy. The rate of photocrosslinking increases with increase in methylene chain. The fluorescence property decreased with successive UV irradiation in the polymers.


Stilbene Char Yield Anhydrous Potassium Carbonate Methylene Chain Methylene Spacer 



We gratefully acknowledge the financial support provided for this research work by Department of Science and Technology, New Delhi, India, under the SERC Scheme (Ref. Sanction No. SR/S1/PC-14/2003).


  1. 1.
    Peng B, Johannsmann D, Rühe J (1999) Macromolecules 32:6759CrossRefGoogle Scholar
  2. 2.
    Leszek M, Jolanta F (1997) React Funct Polym 33:225CrossRefGoogle Scholar
  3. 3.
    Decker C, Bianchi C (2005) J Mater Sci 40:5491. doi: CrossRefGoogle Scholar
  4. 4.
    Petri A, Kummer S, Brauchle CH (1995) Liq Cryst 19:277CrossRefGoogle Scholar
  5. 5.
    Zentel R (1986) Liq Cryst 1:589CrossRefGoogle Scholar
  6. 6.
    Sung HK, Chi HA, Sam RK, Kwangnak K (2005) Dyes Pigm 65:179CrossRefGoogle Scholar
  7. 7.
    Marten J, Erbe A, Critchley K, Bramble JP, Weber E, Evans SD (2008) Langmuir 24:2479CrossRefGoogle Scholar
  8. 8.
    Pucci A, Cuia FD, Signori F, Ruggeri GJ (2007) Mater Chem 17:783CrossRefGoogle Scholar
  9. 9.
    Georgiev G, Cebe P, Capel M (2005) J Mater Sci 40:1141. doi: CrossRefGoogle Scholar
  10. 10.
    Hikmet RAM, Lub J, van den Maassen Brink P (1992) Macromolecules 25:4194CrossRefGoogle Scholar
  11. 11.
    Hikmet RAM, Zwerver BH, Lub J (1994) Macromolecules 27:6722CrossRefGoogle Scholar
  12. 12.
    Young WR, Aviram A, Cox RJ (1972) J Am Chem Soc 94:3976CrossRefGoogle Scholar
  13. 13.
    Rameshbabu K, Kannan P, Velu R, Ramamurthy P (2005) Liq Cryst 32:823CrossRefGoogle Scholar
  14. 14.
    Catanescu O, Grigoras M, Colotin G, Dobreanu A, Hurduc N, Simionescu CI (2001) Eur Polym J 37:2213CrossRefGoogle Scholar
  15. 15.
    Li CH, Chang TC (1990) J Polym Sci Part A Polym Chem 28:3625CrossRefGoogle Scholar
  16. 16.
    Canadell J, Mantecón A, Cádiz V (2008) Polym Degrad Stab 93:59CrossRefGoogle Scholar
  17. 17.
    Kannan P, Murugavel SC (1999) J Polym Sci Part A Polym Chem 37:3285CrossRefGoogle Scholar
  18. 18.
    Kim J, Lee K, Lee K, Bae J, Yang J, Hong S (2003) Polym Degrad Stab 79:201CrossRefGoogle Scholar
  19. 19.
    Xia XN, Luy B, Zhou X, Xiong YO, Zhang XH, Xu WJ (2006) J Appl Polym Sci 102:3842CrossRefGoogle Scholar
  20. 20.
    Hamciuc C, Vlad-Bubulac T, Petreus O, Lisa G (2007) Eur Polym J 43:80Google Scholar
  21. 21.
    Quigliang H, Lei S, Yuan H, Shun Z (2009) J Mater Sci 44:1308. doi: CrossRefGoogle Scholar
  22. 22.
    Canadell J, Mantecon H, Cadiz V (2007) Polym Degrad Stab 92:1934CrossRefGoogle Scholar
  23. 23.
    Senthil S, Kannan P (2002) Liq Cryst 29:1297CrossRefGoogle Scholar
  24. 24.
    Sakthivel P, Kannan P (2006) Liq Cryst 33:341CrossRefGoogle Scholar
  25. 25.
    Perrin DD, Armorego WLF (1988) Purification of laboratory chemicals. Pergamon, New YorkGoogle Scholar
  26. 26.
    Gao C, Hay AS (1995) J Polym Sci Part A Polym Chem 33:2731CrossRefGoogle Scholar
  27. 27.
    Goldschmith DJ, Kennedy E, Campbello RG (1995) J Org Chem 40:3571CrossRefGoogle Scholar
  28. 28.
    Kang SK, Kim WS, Homoon B (1985) Synthesis 12:1161CrossRefGoogle Scholar
  29. 29.
    Antony R (1993) J Polym Sci Part A Polym Chem 31:3187CrossRefGoogle Scholar
  30. 30.
    Bellamy LJ (1980) The infrared spectra of complex molecules, 3rd edn. Chapman and Hall, London, p 1Google Scholar
  31. 31.
    Richards M, Dahiyat BI, Arm DM, Lim S, Leong KW (1991) J Polym Sci Part A Polym Chem 29:1157CrossRefGoogle Scholar
  32. 32.
    Kannan P, Raja S, Sakthivel P (2004) Polymer 45:7895CrossRefGoogle Scholar
  33. 33.
    Al-Muaikel NS (2003) Eur Polym J 39:1025CrossRefGoogle Scholar
  34. 34.
    Huang FJ, Wang TL (2004) J Polym Sci Part A Polym Chem 42:290CrossRefGoogle Scholar
  35. 35.
    Bonet J, Callau L, Reina JA, Galia M, Cadiz V (2002) J Polym Sci Part A Polym Chem 40:3883CrossRefGoogle Scholar
  36. 36.
    Percec V, Kawasumi M (1993) Chem Mater 5:826CrossRefGoogle Scholar
  37. 37.
    Sakthivel P, Kannan P (2005) Polymer 46:9821CrossRefGoogle Scholar
  38. 38.
    Gangadhara, Kishore K (1993) Macromolecules 26:2995CrossRefGoogle Scholar
  39. 39.
    Huang HW, Horie K, Tokita M, Watanabe J (1999) Polymer 40:3013CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Department of ChemistryAnna UniversityChennaiIndia

Personalised recommendations