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Ferrocenyl Monomers and Polymers of N-Allyl and N-Acrylatenaphthalimides

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A series of N-allyl, N-ethylmethacrylate and N-phenylmethacrylatenaphthalimide monomers have been prepared with –C=CFc, –C≡CFc and –C≡CSiMe3 substituents at the 4-position of the naphthalimide ring. All have been characterised by elemental analysis and spectroscopy; the X-ray structure of N-allyl-4-ethenylferrocenylnapththalimide is also reported. Free-radical polymerisation of these monomers gave homopolymers, random co- and terpolymers with polydispersities ranging from 1.7 to 3.2. Incorporation into a polymer matrix has no effect on the spectroscopic and electrochemical properties of the naphthalimide or ferrocenyl components. The ferrocenyl polymers are electrochromic and when oxidised give naphthalimide\({\rightarrow \hbox{Fc}^{+}}\) charge-transfer bands in the NIR; this electrochromism was examined by OTTLE techniques.

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References

  1. (a) J. Morgado, J. Gruner, S. P. Walcott, T. M. Yong, R. Cervini, S. C. Moratti, A. B. Holmes, and R. H. Friend, Synth. Metals, 95, 113 (1998). (b) F. Cacialli, C.-M. Bouche, P. Le Barny, R. H. Friend, H. Facoetti, F. Soyer, and P. Robin, Opt. Mater. 9, 163 (1998)

  2. (a) W. W. Stewart, Nature, 292, 17 (1981). (b) R. J. Hodgkiss, G. W. Jones, A. Long, R. W. Middleton, J. Parrick, M. R. L. Stratford, P. Wardman, and G. D. Wilson, J Med. Chem. 34, 2268 (1991). (c) Z.-R. Liu, K. H. Hecker, and R. L. Rill, J. Biomol. Struct. Dyn. 14, 331 (1996)

  3. (a) Z. D. Tul’guk, R. N. Nurmukhametov, V. G. Klimenko, and L. I. Semenova, Khimicheskie Volokna, 5, 16 (1993). (b) T. Cao and S. E. Webber, Macromolecules, 24, 79 (1991). (c) M. Chen, Y. Hu, H. Yan, and Y. Shen, Youji Huaxue, 21, 294 (2001). (d) I. Grabchev, Dyes Pigments, 38, 219 (1998). (e) T. Philipova, I. Karamancheva, and I. Grabchev, Dyes Pigments, 28, 91 (1995). (f) I. Grabchev, I. Moneva, R. Betcheva, and G. Elyashevich, Mat. Res. Innovat. 6, 34 (2002)

  4. (a) F. S. Du, H. Cai, Z.-C. Li, and F.-M. Li, J. Polym. Sci. Part A: Polym. Chem. 36, 1111 (1998). (b) I. Grabchev and V. J. Bojinov, Photochem. Photobio. A: Chem. 139, 157 (2001)

  5. (a) C. M. Bouche, P. Le Barny, H. Facoetti, and F. Soyer, J. Chimie Phys. Physico-Chimie Biol. 95, 1351 (1998). (b) F. Cacialli, B. Bouche, P. Le Barny, R. H. Friend, H. Facoetti, and F. Soyer, Opt. Mater. 9, 163 (1998). (c) I. Grabchev and J.-M. Chovelon, Polym. Adv. Technol. 14, 601 (2003)

  6. Grabchev I., Moneva I., Bojinov V., Guittonneau S. (2000) J. Mat. Chem 10:1291

    Article  CAS  Google Scholar 

  7. Philipova T., Grabchev I., Petrov I. (1997) J. Polym. Sci., Part A: Polym. Chem. 35:1069

    Article  Google Scholar 

  8. (a) I. Grabchev and V. Bojinov, Polym. Degrad. Stab. 70, 147 (2000) (b) V. Bojinov and T. Konstantinova, Dyes Pigments 54, 239 (2002)

  9. Grabchev I., Chovelon J.-M., Bojinov V., Ivanova G. (2003) Tetrahedron 59:9591

    Article  CAS  Google Scholar 

  10. Arimoto F. S., Haven A. C. (1955) J. Am. Chem. Soc. 77:6295

    Article  CAS  Google Scholar 

  11. C. U. Pittman, J. Inorg. Organomet. Polym. Mater. 15, 33 (2005); A. S. Abd-El-Aziz, C. E. Carraher, C. U. Pittman, J. E. Sheats, and M. Zeldin, eds., Macromolecules Containing Metal and Metal-Like Elements, Vol. 2 Organoiron Polymers. (John Wiley & Sons Publishers, Hoboken, N. J., 2004)

  12. A. S. Abd-El-Aziz, C. E. Carraher, C. U. Pittman, J. E. Sheats, and M. Zeldin, eds. Macromolecules Containing Metal and Metal-Like Elements, Volume 1: A Half-Century of Metal- and Metalloid-Containing Polymers. (John Wiley & Sons Publishers, Hoboken, N. J., 2003)

  13. McAdam C. J., Robinson B. H., Simpson J. (2000) Organometallics 19:3644

    Article  CAS  Google Scholar 

  14. McAdam C. J., Morgan J. L., Robinson B. H., Simpson J., Rieger P. H., Rieger A. L. (2003) Organometallics 22:5126

    Article  CAS  Google Scholar 

  15. Cavigiolio G., Morgan J. L., Robinson B. H., Simpson J. (2004) Aust. J. Chem. 57:885

    Article  CAS  Google Scholar 

  16. McAdam C. J., Morgan J. L., Murray R. E., Robinson B. H., Simpson J. (2004) Aust. J. Chem. 57:525

    Article  CAS  Google Scholar 

  17. (a) A. H. Flood, C. J. McAdam, K. C. Gordon, H. G. Kjaergaard, A. M. Manning, B. H. Robinson, and J. Simpson, Polyhedron, in press. (b) L. Cuffe, R. D. A. Hudson, J. F. Gallagher, S. Jennings, C. J. McAdam, R. B. Connelly, A. R. Manning, B. H.Robinson, and J. Simpson, Organometallics, 24, 2051 (2005). (c) P. Chandrasekhar, B. J. Zay, G. C. Birur, S. Rawal, E. A. Pierson, L. Kauder, and T. Swanson, Adv. Funct. Mater. 12, 95 (2002).

  18. J. M. Warman, R. D. Abellon, and H. J. Verhey, J. Phys. Chem. B, 101, 4913 (1997). (b) B. H. Cumpston, S. P. Ananthavel, and S. Barlow, Nature, 398, 51 (1999)

    Google Scholar 

  19. Liu W.-Y., Xu Q.-H., Ma Y.-X., Liang Y.-M., Dong N.-L., Guan D.-P. (2001) J. Organometal. Chem. 625:128

    Article  CAS  Google Scholar 

  20. Abram T. S., Watts W. E. (1976) Synth. React. Inorg. Metal-Org. Chem. 6:31

    CAS  Google Scholar 

  21. Konstantinova T. N., Meallier P., Grabchev I. (1993) Dyes Pigments 22:191

    Article  CAS  Google Scholar 

  22. Grayshan P. H., Kadhim A. M., Peters A. T. (1974) J. Heterocyclic Chem. 11:33

    Article  CAS  Google Scholar 

  23. SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, (1999)

  24. G. M. Sheldrick, SHELXS-97 A program for the solution of crystal structures from diffraction data and SHELXL-97 A program for the refinement of crystal structures; University of Göttingen, Germany (1997)

  25. Easton C. J., Gulbis J. M., Hoskins B. F., Scharfbillig I. M., Tiekink E. R. T. (1992) Z. Kristallogr. 199:249

    Article  CAS  Google Scholar 

  26. (a) R. G. Baughman, S. C.Chang, R. E. Utecht, and R. D. Lewis, Acta Crystallogr. C51, 1189 (1995). (b) R. A. Batchelor, C. A. Hunter, and J. Simpson, Acta Crystallogr. C53, 1117 (1997). (c) S. V. Lindeman, I. I. Ponomarev, and A. L. Rusanov, Acta Crystallogr. C51, 2157 (1995). (d) Y. Dromzee, J. Kossanyi, V. Wintgens, P. Valat, L. Biczok, A. Demeter, and T. Z. Berces, Z. Krystallogr. 210, 760 (1995)

  27. Janiak C. (2000) J. Chem Soc. Dalton Trans. 3885

  28. Spek A. L. (2003) J. Appl. Cryst. 36:7

    Article  CAS  Google Scholar 

  29. Pittman C. U., Hirao A. (1978) J. Polym. Sci., Chem. Ed. 16:1197

    Article  CAS  Google Scholar 

  30. C. U. Pittman, J. C. Lai, D. P. Vanderpool, M. Good, and R. Prados in Polymer Characterisation: Interdisciplinary Approaches, C. D. Carver, ed. (Plenum Press, NY, 1971)

  31. M. George and G. Hayes, J. Polym. Sci. Chem. Ed. 13, 1049 (1976); M. George and G. Hayes, J. Polym. Sci. Chem. Ed. 14, 475 (1976); M. George and G. Hayes, Polymer 15, 394 (1974)

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Acknowledgements

This work was supported by a grant from the New Economy Research Fund of the New Zealand Foundation for Research Science and Technology. We also thank the New Zealand Foundation for Research Science and Technology for a Postdoctoral Fellowship to C.J.M.

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  1. Department of Chemistry, University of Otago, Dunedin, New Zealand

    Bogdan H. Dana, C. John McAdam, Brian H. Robinson, Jim Simpson & Hongsheng Wang

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  1. Bogdan H. Dana
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  2. C. John McAdam
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Correspondence to Jim Simpson.

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Dana, B.H., McAdam, C.J., Robinson, B.H. et al. Ferrocenyl Monomers and Polymers of N-Allyl and N-Acrylatenaphthalimides. J Inorg Organomet Polym 17, 547–559 (2007). https://doi.org/10.1007/s10904-007-9144-1

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