Skip to main content
Log in

Synthesis of a main-chain liquid crystalline azo-polymer via “click” chemistry

  • Short Communication
  • Published:
Colloid and Polymer Science Aims and scope Submit manuscript

Abstract

A main-chain liquid crystalline azo-polymer (BPHCHA) was prepared through the copper-catalyzed “click” reaction between the alkyne group on 4,4′-bis((6-(propargyloxy)hexyl)oxy) biphenyl (BPH) and the azide group on 4-(6-azidohexyloxy)carbonyl-4′-(6′-azidohexyloxy) azobenzene (AHCHA). The “click” reaction was confirmed by FT-IR, 1H NMR, and GPC studies. The phase transition behavior of BPH, AHCHA, and the resulting azo-polymer BPHCHA was investigated by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). AHCHA and BPHCHA exhibited mesomorphic behavior, while BPH is a crystalline compound. A liquid crystalline phase from 39 to 69 °C for AHCHA upon heating was observed under POM. Schlieren texture was observed at 130 °C for BPHCHA on cooling from 150 °C and annealed at 130 °C for 15 min. Moreover, DSC and POM studies showed that BPHCHA exhibited monotropic mesomorphic behavior.

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
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

References

  1. Audorff H, Kreger K, Walker R, Haarer D, Kador L, Schmidt HW (2010) Adv Polym Sci 228:59

    Article  CAS  Google Scholar 

  2. Zhao Y, He J (2009) Soft Matter 5:2686

    Article  CAS  Google Scholar 

  3. Yan Z, Ji X, Wu W, Wei J, Yu YL (2012) Macromol Rapid Commun 33:1362

    Article  CAS  Google Scholar 

  4. Srinivasan MV, Kannan P (2011) J Mater Sci 46:5029

    Article  Google Scholar 

  5. Tripathy SK, Viswanathan NK, Balasubramanian S, Kumar J (2000) Polym Adv Technol 11:570

    Article  CAS  Google Scholar 

  6. Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004

    Article  CAS  Google Scholar 

  7. Huisgen R (1963) Angew Chem Int Ed 2:565

    Article  Google Scholar 

  8. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    Article  CAS  Google Scholar 

  9. Tornoe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Article  CAS  Google Scholar 

  10. Reinicke S, Schmalz H (2011) Colloid Polym Sci 289:497

    Article  CAS  Google Scholar 

  11. Chen JC, Wang HD, Luo WQ, Xiang JM, Zhang LH, Sun BB (2010) Colloid Polym Sci 288:173

    Article  CAS  Google Scholar 

  12. Ho KM, Li WY, Wong CH, Li P (2010) Colloid Polym Sci 288:1503

    Article  CAS  Google Scholar 

  13. Sumerlin BS, Tsarevsky NV, Louche G, Lee RY, Matyjaszewski K (2005) Macromolecules 38:7540

    Article  CAS  Google Scholar 

  14. Englert BC, Bakbak S, Bunz UHF (2005) Macromolecules 38:5868

    Article  CAS  Google Scholar 

  15. Ladmiral V, Mantovani G, Clarkson GJ, Cauet S, Irwin JL, Haddleton DM (2006) J Am Chem Soc 128:4823

    Article  CAS  Google Scholar 

  16. Xia Y, Verduzco R, Grubbs RH, Kornfield JA (2008) J Am Chem Soc 130:1735

    Article  CAS  Google Scholar 

  17. Parrish B, Breitenkamp RB, Emrick T (2005) J Am Chem Soc 127:7404

    Article  CAS  Google Scholar 

  18. Liu XM, Quan LD, Tian J, Laquer FC, Ciborowski P, Wang D (2010) Biomacromolecules 11:2621

    Article  CAS  Google Scholar 

  19. Helms B, Mynar JL, Hawker CJ, Frechet JMJ (2004) J Am Chem Soc 126:15020

    Article  CAS  Google Scholar 

  20. Joralemon MJ, O’Reilly RK, Matson JB, Nugent AK, Hawker CJ, Wooley KL (2005) Macromolecules 38:5436

    Article  CAS  Google Scholar 

  21. Ossipov DA, Hilborn J (2006) Macromolecules 39:1709

    Article  CAS  Google Scholar 

  22. Laurent BA, Grayson SM (2006) J Am Chem Soc 128:4238

    Article  CAS  Google Scholar 

  23. Fernandez-Megia E, Correa J, Rodriguez-Meizoso I, Riguera R (2006) Macromolecules 39:2113

    Article  CAS  Google Scholar 

  24. Johnson JA, Lewis DR, Diaz DD, Finn MG, Koberstein JT, Turro NJ (2006) J Am Chem Soc 128:6564

    Article  CAS  Google Scholar 

  25. Cui ZH, Zhang Y, He SJ (2008) Colloid Polym Sci 286:1553

    Article  CAS  Google Scholar 

  26. Pandey S, Kolli B, Mishra SP, Samui AB (2012) J Polym Sci A Polym Chem 50:1205

    Article  CAS  Google Scholar 

  27. Royes J, Rebole J, Custardoy L, Gimeno N, Oriol L, Tejedor RM, Pinol M (2012) J Polym Sci A Polym Chem 50:1579

    Article  CAS  Google Scholar 

  28. Pandey S, Mishra SP, Kolli B, Kanai T, Samui AB (2012) J Polym Sci A Polym Chem 50:2659

    Article  CAS  Google Scholar 

  29. Yuan WZ, Yu ZQ, Tang YH, Lam JWY, Xie N, Lu P, Chen EQ, Tang BZ (2011) Macromolecules 44:9618

    Article  CAS  Google Scholar 

  30. Nithyanandan S, Balamurugan S, Senthil S (2009) Chin J Polym Sci 27:761

    Article  Google Scholar 

  31. Gujadhur R, Venkataraman D, Kintigh JT (2001) Tetrahedron Lett 42:4791

    Article  CAS  Google Scholar 

  32. Chen D, Liu H, Kobayashi T, Yu HF (2010) J Mater Chem 20:3610

    Article  CAS  Google Scholar 

  33. Stenhouse PJ, Valles EM, Kantor SW, MacKnight WJ (1989) Macromolecules 22:1467

    Article  CAS  Google Scholar 

  34. Angeloni AS, Laus M, Chiellini E, Galli G, Francescangeli O (1995) Eur Polym J 31:253

    Article  CAS  Google Scholar 

  35. Xue XQ, Zhu J, Zhang W, Zhang ZB, Zhu XL (2009) Polymer 50:4512

    Article  CAS  Google Scholar 

Download references

Acknowledgment

We thank the Natural Science Foundation of Tianjin (10JCYBJC02100) for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Shangjin He.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kang, X., Zhao, J., Li, H. et al. Synthesis of a main-chain liquid crystalline azo-polymer via “click” chemistry. Colloid Polym Sci 291, 2245–2251 (2013). https://doi.org/10.1007/s00396-013-2946-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00396-013-2946-5

Keywords

Navigation