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Synthesis and Characterization of New Functional Polystyrenes Containing Tributyltin Carboxylate Moieties Linked to the Aromatic Ring by a Trimethylene Spacer

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Abstract

A novel trialkyltin carboxylate monomer, tributyltin 4-(p-styryl)-butanoate, characterized by the presence of a trimethylenic spacer linking the tin carboxylate moiety to the aromatic group, has been prepared and submitted to radical homo- and copolymerization with styrene in order to obtain the corresponding copolymers with variable contents of organometallic moiety. For the sake of comparison, tributyltin 4-(4-isopropylphenyl)-butanoate has also been synthesized as the structural model of the repeating unit of the polymers. All the products prepared have been characterized both in solution and in the solid state by spectroscopic and thermal techniques with the aim to establish the coordination state of the tin atom, a feature which is of importance for future application of these derivatives.

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References

  1. J.A. Thompson, M.G. Sheffer, R.C. Pierce, Y.K. Chau, J.J. Cooney, W.P. Cullen, R.J. Maguire, Organotin Compounds in the Aquatic Environment: Scientific Criteria for Assessing their Effects on Environmental Quality (National Research Council Canada, Ottawa, 1985), p. 284

    Google Scholar 

  2. A.G. Davies, Organotin Chemistry, Chapter 1 (VCH, Weinheim, 2004)

    Google Scholar 

  3. R.W. Johnson, in Annual Technical Conference – Society of Plastic Engineers, Vol. 3 (Society of Plastic Engineers, Brookfield, 2003), pp. 3080–3082

  4. R. Gächter, H. Müller, Plastics Additives Handbook Chapter 4 (Hanser Publisher, Munich, 1990), pp. 281–287

    Google Scholar 

  5. D. Seyferth, T.C. Masterman, Appl. Organomet. Chem. 8(4), 335 (1994) and references therein

    Article  CAS  Google Scholar 

  6. H. Rüdel, Ecotoxicol. Environ. Safety 56(1), 180 (2003)

    Article  CAS  Google Scholar 

  7. J. Otera, Chem. Rev. 93(4), 1449 (1993)

    Article  CAS  Google Scholar 

  8. J. Otera, Acc. Chem. Res. 37(5), 288 (2004)

    Article  CAS  Google Scholar 

  9. K.E. Appel, Drug Metabol. Rev. 36(3–4), 763 (2004)

    Article  CAS  Google Scholar 

  10. M.A. Champ, P.F. Seligman, Organotins, Environmental Fate and Effects (Chapman and Hall, London, 1996)

    Google Scholar 

  11. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, M. Biesemans, Appl. Organomet. Chem. 19(7), 841 (2005)

    Article  CAS  Google Scholar 

  12. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, M. Biesemans, J. Polym. Sci. Part A: Polym. Chem. 43(14), 3091 (2005)

    Article  CAS  Google Scholar 

  13. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, M. Biesemans, J. Organomet. Chem. 691(13), 3043 (2006)

    Article  CAS  Google Scholar 

  14. H. Dalil, M. Biesemans, R. Willem, L. Angiolini, E. Salatelli, D. Caretti, N. Chaniotakis, K. Perdikaki, Helv. Chim. Acta 85, 852 (2002)

    Article  CAS  Google Scholar 

  15. D.D. Perrin, W.L.F. Amarego, D.R. Perrin, Purification of Laboratory Chemicals (Pergamon Press Ltd, Oxford, 1966)

    Google Scholar 

  16. D.J. Cram, L.A. Singer, J. Am. Chem. Soc. 85, 1084 (1963)

    Article  CAS  Google Scholar 

  17. J.R. Prahlad, S. Dev, Tetrahedron. 26(2), 631 (1970)

    Article  CAS  Google Scholar 

  18. L.I. Smith, C.P. Lo, J. Am. Chem. Soc. 70, 2209 (1948)

    Article  CAS  Google Scholar 

  19. R.O. Clinton, S.C. Laskowski, J. Am. Chem. Soc. 70, 3135 (1948)

    Article  CAS  Google Scholar 

  20. R.K. Ingham, S.D. Rosenberg, H. Gilman, Chem. Rev. 60, 459 (1960)

    Article  CAS  Google Scholar 

  21. V.V. Korshak, A.M. Polyakova, M.D. Suchkova, Vysokomol. Soedin. 2(1), 13 (1960)

    CAS  Google Scholar 

  22. S.M. Samoilov, Vysokomol. Soedin. B 16(1), 42 (1974)

    CAS  Google Scholar 

  23. N.E. Ikladious, N.N. Messiha, A.F. Shaaban, Eur. Polym. J. 20(6), 625 (1984)

    Article  CAS  Google Scholar 

  24. S.S.S. Al-Diab, H.-K. Suh, J.E. Mark, H. Zimmer, J. Polym. Sci. Part A: Polym. Chem. 28(2), 299 (1990)

    Article  CAS  Google Scholar 

  25. J. Holeček, K. Handlíř, A. Lyčka, T.K. Chattopadhyay, B. Majee, A.K. Kumar, Coll. Czech. Chem. Commun. 51(5), 1100 (1986)

    Article  Google Scholar 

  26. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, C. Femoni, J. Organomet. Chem. 689(21), 3301 (2004)

    Article  CAS  Google Scholar 

  27. R.J. Newman, Chem. Phys. 20, 1663 (1952)

    Article  CAS  Google Scholar 

  28. R.M. Silverstein, G. Clayton Bassler, T.C. Morrill, Spectrometric Identification of Organic Compounds, 4th edn. (John Wiley and Sons, New York, 1981) p.122

    Google Scholar 

  29. M.J. Janssen, J.G.A. Luijten, G.J.M. Van der Kerk, Rec. Trav. Chim. 82, 90 (1963)

    Article  CAS  Google Scholar 

  30. J. Holeček, M. Nádvorník, K. Handlíř, A. Lyčka, J. Organomet. Chem. 241(2), 177 (1983)

    Article  Google Scholar 

  31. J. Holeček, K. Handlíř, M. Nádvorník, A. Lyčka, J. Organomet. Chem. 258(2), 147 (1983)

    Article  Google Scholar 

  32. A. Lyčka, M. Nádvorník, K. Handlíř, J. Holeček, Coll. Czech. Chem. Commun. 49(6), 1497 (1984)

    Google Scholar 

  33. L. Angiolini, M. Biesemans, D. Caretti, E. Salatelli, R. Willem, Polymer 41(11), 3913 (2000)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The financial support by the University of Bologna (Progetti Pluriennali di Ricerca 2003) to L.A., D.C., L.M. and E.S. as well as by the fund of Scientific Research Flanders (Belgium) (FWO) (Grants G 0016.02 & G.0469.06) and the Research Council (Onderzoeksraad) of the Vrije Universiteit Brussel (Concerted Research Action, Grant GOA31) to R. W. and M. B. is gratefully acknowledged.

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Correspondence to Luigi Angiolini.

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Angiolini, L., Caretti, D., Salatelli, E. et al. Synthesis and Characterization of New Functional Polystyrenes Containing Tributyltin Carboxylate Moieties Linked to the Aromatic Ring by a Trimethylene Spacer. J Inorg Organomet Polym 18, 236–245 (2008). https://doi.org/10.1007/s10904-007-9166-8

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