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Synthesis of a novel class of chromophoric cross-linkers

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Abstract

Considering the special place of aromatic diazo compounds in photo-responsive materials and growing demand for materials with interesting optical properties, a new class of chromophoric cross-linkers was synthesized by acrylation of diazo derivatives of m-diaminobenzene. The cross-linkers are soluble in a wide variety of organic solvents as well as in mixtures of water and water miscible solvents. The chromophores of the cross-linkers are stable in protic and some certain aprotic solvents and remain stable after cross-linking. The chemical structure of this class allows one to have a cross-linker with tuned chemical reactivity and solubility with post-linking applicability. The cross-linkers are obtained from reactions with simple chemistry in high yields and are able to participate in radical and ionic polymerization as well as in nucleophilic addition reactions. Successful participation of these substances in acrylamide polymerization and sol–gel preparation is demonstrated.

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References

  1. V. Percec, Chem. Rev. 101, 3579 (2001)

    Article  CAS  Google Scholar 

  2. D.B. Otts, M.W. Urban, Polymer 46, 2699 (2005)

    Article  CAS  Google Scholar 

  3. M.R. Buchmeiser, J. Chromatogr. A 918, 233 (2001)

    Article  CAS  Google Scholar 

  4. S. Al-Kindy, R. Badía, J.L. Suárez-Rodríguez, M.E. Díaz-García, Crit. Rev. Anal. Chem. 30, 291 (2000)

    Article  CAS  Google Scholar 

  5. F. Falvo, L. Fiebig, M. Schäfer, Int. J. Mass Spectrom. 354, 26 (2013)

    Article  Google Scholar 

  6. K. Sato, K. Hosokawa, M. Maeda, Anal. Sci. 23, 17 (2007)

    Article  Google Scholar 

  7. S.A. Piletsky, T.L. Panasyuk, E.V. Piletskaya, I.A. Nicholls, M. Ulbricht, J. Membr. Sci. 157, 263 (1999)

    Article  CAS  Google Scholar 

  8. W.E. Hennink, C.F. van Nostrum, Adv. Drug Deliv. Rev. 54, 13 (2002)

    Article  CAS  Google Scholar 

  9. G. Leriche, L. Chisholm, A. Wagner, Bioorg. Med. Chem. 20, 571 (2012)

    Article  CAS  Google Scholar 

  10. M. Suchanek, A. Radzikowska, C. Thiele, Nat. Methods 2, 261 (2005)

    Article  CAS  Google Scholar 

  11. W. Wu, A.D. Li, Nanomedicine 2, 523 (2007)

    Article  CAS  Google Scholar 

  12. D.A. Spivak, Adv. Drug Deliv. Rev. 57, 1779 (2005)

    Article  CAS  Google Scholar 

  13. M.W. Gardner, L.A. Vasicek, S. Shabbir, E.V. Anslyn, J.S. Brodbelt, Anal. Chem. 80, 4807 (2008)

    Article  CAS  Google Scholar 

  14. R.N. Wine, J.M. Dial, K.B. Tomer, C.H. Borchers, Anal. Chem. 74, 1939 (2002)

    Article  CAS  Google Scholar 

  15. D. Filpula, H. Zhao, Adv. Drug Deliv. Rev. 60, 29 (2008)

    Article  CAS  Google Scholar 

  16. S. Rouhani, S. Salimi, K. Haghbeen, Dyes Pigm. 77, 363 (2008)

    Article  CAS  Google Scholar 

  17. D. Wang, X. Wang, Prog. Polym. Sci. 38, 271 (2013)

    Article  CAS  Google Scholar 

  18. A. Priimagi, C.J. Barrett, A. Shishido, J. Matter Chem. C 2, 7155 (2014)

    Article  CAS  Google Scholar 

  19. H. Gao, K. Matyjaszewski, Prog. Polym. Sci. 34, 317 (2009)

    Article  CAS  Google Scholar 

  20. K. Haghbeen, E.W. Tan, J. Org. Chem. 63, 4503 (1998)

    Article  CAS  Google Scholar 

  21. M. Constantin, G. Fundueanu, M. Nichifor, Rev. Roum. Chem. 53(9), 753 (2008)

    Google Scholar 

  22. L. Chi, O. Sadovski, G.A. Woolley, Biocon. Chem. 17, 670 (2006)

    Article  CAS  Google Scholar 

  23. F. Mirazizi, A. Bahrami, K. Haghbeen, H.S. Zahiri, M. Bakavoli, R.L. Legge, J. Enzyme Inhib. Med. Chem. Online (2015). doi:10.3109/14756366.2015.1103234

    Google Scholar 

  24. M. Shamsipura, B. Maddah, B. Hemmateenejad, S. Rouhani, K. Haghbeen, K. Alizadeh, Spectrochimica Acta Part A 70, 1–6 (2008)

    Article  Google Scholar 

  25. K. Haghbeen, R. Agharafeie, S. Maghsoudi, Iran. Polym. J. 14, 729 (2005)

    CAS  Google Scholar 

  26. K. Haghbeen, R.L. Legge, Chem. Eng. J. 150, 1 (2009)

    Article  CAS  Google Scholar 

  27. R. Haag, S. Roller, in Immobilized Catalysts, ed. (Springer, Berlin Heidelberg) (2004)

  28. R. Mutneja, R. Singh, V. Kaur, J. Wagler, E. Kroke, Dyes Pigm. 108, 41 (2014)

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the Natural Sciences and Engineering Research Council (NSERC) in the form of a Discovery Grant to RLL. Sincere collaboration of Dr Richard W. Smith manager of Mass Spectrometry Facility of University of Waterloo is appreciated.

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Authors and Affiliations

  1. National Institute for Genetic Engineering and Biotechnology, P.O.Box: 14965/161, Tehran, Iran

    Kamahldin Haghbeen

  2. Department of Chemical Engineering, University of Waterloo, Waterloo, ON, N2L 3G1, Canada

    Raymond L. Legge

Authors
  1. Kamahldin Haghbeen
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  2. Raymond L. Legge
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Correspondence to Kamahldin Haghbeen.

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Haghbeen, K., Legge, R.L. Synthesis of a novel class of chromophoric cross-linkers. J IRAN CHEM SOC 13, 957–965 (2016). https://doi.org/10.1007/s13738-016-0811-4

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  • DOI: https://doi.org/10.1007/s13738-016-0811-4

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