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Recent advances in the synthesis and applications of azo initiators

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Abstract

This mini-review describes recent developments and trends in the area of syntheses and applications of azo compounds, which are planned to act as initiators of radical reactions, particularly polymerizations. The paper reports chemical modifications of well-known initiators (AIBN, etc.) or variants of syntheses of new types of these compounds. The chemical modifications of basic skeletons of azo initiators are discussed in the context with their properties and applications. Also discussed are the contemporary trends in the development of these initiators, particularly in preparation of microparticles and nanoparticles of polymers or hybrid inorganic–organic microparticles and nanoparticles prepared for intentional studies and applications.

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Abbreviations

AIBN:

Azobisisobutyronitrile

DCC:

Dicykohexylcarbodiimide

DMAP:

4-Dimethylaminopyridine

PLP:

Pulsed-laser polymerization

RAFT:

Reversible addition fragmentation chain transfer

References

  1. G.A. Ozin, A.C. Arsenault, Nanochemistry: a chemical approach to nanomaterials, 1st edn. (RSC Publishing, Cambridge, 2005), pp. 435–462

    Google Scholar 

  2. B.G. Trewin, H.-T. Chen, V.S.-Y. Lin, in Recoverable and recyclable catalysts, ed. by M. Benaglia (Wiley, Chichester, 2009), p. 15

    Chapter  Google Scholar 

  3. O. Prucker, J. Rühe, Macromolecules 31, 592 (1998)

    Article  CAS  Google Scholar 

  4. O. Prucker, J. Rühe, Macromolecules 31, 602 (1998)

    Article  CAS  Google Scholar 

  5. http://www.wako-chem.co.jp/specialty/index.htm

  6. H.D. Hatrzler, in The chemistry of the cyano group, ed. by S. Patai (Wiley, Chichester, 1970), p. 683

    Google Scholar 

  7. T.N. Myers, in Encyclopedia of polymer science and technology, ed. by K. Matyjaszewski (Wiley Online Library, New York, 2002), p. 563

    Google Scholar 

  8. A. Strecker, A. Ann. 75, 27 (1850)

    Google Scholar 

  9. P. Drabina, M. Sedlák, ARKIVOC Special Issue 1, 152 (2012)

    Google Scholar 

  10. J. Thiel, K. Heuser, Justus Liebigs Ann. Chem. 290, 1 (1896)

    Article  Google Scholar 

  11. C.G. Overberger, P. Huang, M.B. Berenbaum, N.J. Leonard, E.H. Mottus, Org. Synth. Coll. 4, 274 (1963)

    Google Scholar 

  12. J.P. Van Hook, A.V. Tobolsky, J. Am. Chem. Soc. 80, 779 (1958)

    Article  Google Scholar 

  13. P.B. Ayscough, B.R. Brooks, H.E. Evans, J. Phys. Chem. 68, 3889 (1964)

    Article  CAS  Google Scholar 

  14. M. Talât-Erben, S. Bywater, J. Am. Chem. Soc. 77, 3710 (1955)

    Article  Google Scholar 

  15. M. Talât-Erben, S. Bywater, J. Am. Chem. Soc. 77, 3712 (1955)

    Article  Google Scholar 

  16. C.G. Overberger, H. Biletch, A.B. Finestone, J. Lilker, J. Herbert, J. Am. Chem. Soc. 75, 2078 (1953)

    Article  CAS  Google Scholar 

  17. A.F. Bickel, V.A. Waters, Recl. Trav. Chim. Pays-Bas 69, 1490 (1950)

    Article  CAS  Google Scholar 

  18. B.V. Tamhankar, U.V. Desai, R.B. Mane, P.P. Kulkarni, P.P. Wadgaonkar, Synth. Commun. 32, 3643 (2002)

    Article  CAS  Google Scholar 

  19. T. Watanabe, O. Koshikawa, S. Shikida, JP 2007070230, 2007. Chem. Abstr. 146, 337893 (2007)

    Google Scholar 

  20. A. Pinner, Ber. Dtsch. Chem. Ges. 16, 1643 (1883)

    Article  Google Scholar 

  21. K. Tauer, in Advanced polymer nanoparticles: synthesis and surface modifications, ed. by V. Mittal (CRC Press, Boca Raton, 2011), p. 329

    Google Scholar 

  22. M. Sedlák, K. Tauer, Molecules 5, 730 (2000)

    Article  Google Scholar 

  23. K. Suguru, H. Seji, S. Kazuo, EP 1999-109142, 1999, Chemical Abstract 131, 351803 (1999)

  24. J.J. Ritter, P.P. Minieri, J. Am. Chem. Soc. 70, 4045 (1948)

    Article  CAS  Google Scholar 

  25. M. Sedlák, K. Tauer, SYNLETT Issue 2, 299–300 (2004)

  26. K. Tauer, K.A.M. Imroz, U. Yildiz, M. Sedlák, Polymer 46, 1003 (2005)

    Article  CAS  Google Scholar 

  27. A.M. Imroz, K. Tauer, M. Sedlák, Polymer 46, 1017 (2005)

    Article  Google Scholar 

  28. K. Tauer, A.M. Imroz, M. Sedlák, Colloid Polym. Sci. 283, 351 (2005)

    Article  CAS  Google Scholar 

  29. K. Tauer, K.H. Goebel, S. Kosmella, K. Stähler, J. Neelsen, Makromol. Chem. Macromol. Symp. 31, 107 (1990)

    Article  Google Scholar 

  30. U. Yildiz, B. Hazer, I. Capek, Angew. Makromol. Chem. 231, 135 (1995)

    Article  CAS  Google Scholar 

  31. U. Yildiz, B. Hazer, K. Tauer, Polym. Chem. 3, 1107 (2012)

    Article  CAS  Google Scholar 

  32. R. Walz, B. Bömer, W. Heitz, Makromol. Chem. Phys. 178, 2527 (1977)

    CAS  Google Scholar 

  33. B. Hazer, A. Ayas, N. Beşirli, N. Saltek, B.M. Baysal, Makromol. Chem. Phys. 190, 1987 (1989)

    Article  CAS  Google Scholar 

  34. B. Hazer, Macromol. Chem. Phys. 193, 1081 (1992)

    Article  CAS  Google Scholar 

  35. B. Hazer, I. Cakmak, S. Denizligil, Y. Yagci, Angew. Makromol. Chem. 195, 121 (1992)

    Article  CAS  Google Scholar 

  36. B. Hazer, B. Erdem, R.W. Lenz, J. Polym. Sci. Part A Polym. Chem. 32, 1739 (1994)

    Article  CAS  Google Scholar 

  37. U. Yildiz, B. Hazer, Polymer 41, 539 (2000)

    Article  CAS  Google Scholar 

  38. S. Edmondson, V.L. Osborne, W.T.S. Huck, Chem. Soc. Rev. 33, 14 (2004)

    Article  CAS  Google Scholar 

  39. O. Prucker, J. Rühe, Langmuir 14, 6893 (1998)

    Article  CAS  Google Scholar 

  40. R.T. Arnold, G.R. Sheppard, J. Locklin, Macromolecules 45, 5444 (2012)

    Article  CAS  Google Scholar 

  41. V.N. Wong, G. Fernando, A.R. Wagner, J. Zhang, G.R. Kinsel, S. Zauscher, D.J. Dyer, Langmuir 25, 1459 (2009)

    Article  CAS  Google Scholar 

  42. R. Rotzoll, P. Vana, Macromol. Rapid Commun. 30, 1989 (2009)

    Article  CAS  Google Scholar 

  43. R. Rotzoll, P. Vana, Aust. J. Chem. 62, 1473 (2009)

    Article  CAS  Google Scholar 

  44. V.N. Postnov, N.A. Mel’nikova, I.V. Murin, Russ. J. Gen. Chem. 84, 822 (2014)

    Article  CAS  Google Scholar 

  45. H. Yang, H. Pu, F. Gong, J. Appl. Polym. Sci. 131, 41062 (2014)

    Google Scholar 

  46. N. Tsubokawa, Y. Shirai, K. Hashimoto, Colloid Polym. Sci. 273, 1049 (1995)

    Article  CAS  Google Scholar 

  47. D.L. Patton, K.A. Page, Ch. Xu, K.L. Genson, M.J. Fasolka, K.L. Beers, Macromolecules 40, 6017 (2007)

    Article  CAS  Google Scholar 

  48. T. Yakushiji, K. Sakai, A. Kikuchi, T. Aoyagi, Y. Sakurai, T. Okano, Anal. Chem. 71, 1125 (1999)

    Article  CAS  Google Scholar 

  49. J. Chiefari, Y.K. Chong, F. Ercole, J. Kristina, J. Jeffery, P.T. Le Tam, T.A.M. Roshan, F.M. Gordon, M.L. Catherine, E. Rizzardo, H.T. San, Macromolecules 31, 5559 (1998)

    Article  CAS  Google Scholar 

  50. M.D. Soucek, K.R. Miller, U.S. Patent 2,014,0054162, 2014, Chemical Abstract 160, 341478 (2014)

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Acknowledgments

The authors acknowledge financial support from The Czech Grant Agency Project No. 14-00925S.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10, Pardubice, Czech Republic

    Ladislav Androvič, Jan Bartáček & Miloš Sedlák

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  1. Ladislav Androvič
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  2. Jan Bartáček
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  3. Miloš Sedlák
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Correspondence to Miloš Sedlák.

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Androvič, L., Bartáček, J. & Sedlák, M. Recent advances in the synthesis and applications of azo initiators. Res Chem Intermed 42, 5133–5145 (2016). https://doi.org/10.1007/s11164-015-2351-4

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