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Proton Sensing Color Changing Organoiron and Organic Macromolecules

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Abstract

Macromolecules incorporating photoactive species have become one of the most important topics in literature for the search of new materials with tunable properties. In particular, azobenzene-containing polymers have witnessed important developments in order to build up novel, smart materials for various useful purposes. The majority of these materials were completely organic macromolecules, however in recent years, azo dyes have been merged into organometallic polymers. Our group was one of the pioneers in this field via functionalization of organoiron macromolecules with aryl and hetaryl azo moieties. The combination of azo chromophore with organometallic macromolecules can tune the properties of the obtained polymers and increase the possibility of their applications in fields such as reversible optical storage systems, electrooptic modulators, labeling, photorefractive switches and biomedicine. Herein, we are highlighting the synthesis and characterization of various classes of highly colored organo and/or organoiron polymers and illustrating their possible applications.

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References

  1. D.A. Schlüter, C. Hawker, J. Sakamoto, Synthesis of Polymers: New structures and Methods (Wiley, New York, 2012)

    Google Scholar 

  2. D. Yan, C. Gao, H. Frey, Hyperbranched Polymers: Synthesis, Properties, and Applications (Wiley, New York, 2011)

    Book  Google Scholar 

  3. E.W. Neuse, J. Inorg. Organomet. Polym Mater. 15, 3 (2005)

    Article  CAS  Google Scholar 

  4. G. Caldwell, M.G. Meirim, D.D. N’Da, E.W. Neuse, J. Appl. Polym. Sci. 100, 3415 (2006)

    Article  CAS  Google Scholar 

  5. B.A. Aderibigbe, K.D. Jacques, E.W. Neuse, J. Inorg. Organomet. Polym Mater. 21, 336 (2011)

    Article  CAS  Google Scholar 

  6. A.S. Abd-El-Aziz, C.E. Carraher, C.U. Pittman, J.E. Sheats, M. Zeldin (eds.), Macromolecules Containing Metal and Metal-like Elements: A half-century of Metal- and Metalloid-Containing Polymers (Wiley, New York, 2003)

    Google Scholar 

  7. D.D. N’Da, E.W. Neuse, J. Inorg. Organomet. Polym Mater. 20, 468 (2010)

    Article  Google Scholar 

  8. J. Cui, A.D. Campo, Smart Polymers and Their Applications, vol. 93 (Woodhead Publishing, Cambridge, 2014)

    Google Scholar 

  9. Y. Hu, B. Wang, Z. Su, J. Appl. Poly. Sci. 111, 1931 (2009)

    Article  CAS  Google Scholar 

  10. T. Yamamoto, Poly. J. 45, 711 (2013)

    Article  CAS  Google Scholar 

  11. X. Shen, H. Liu, Y. Li, S. Liu, Macromolecules 41, 2421 (2008)

    Article  CAS  Google Scholar 

  12. R.L.M. Allen, In Colour Chemistry (Appleton-Century-Crofts, New York, 1971)

    Google Scholar 

  13. H. Zollinger, In Azo and Diazo Chemistry (Inter science Publishing, New York, 1961)

    Google Scholar 

  14. A. Altomare, C. Baronti, R. Solaro, Macrmol. Chem. Phys. 203, 1584 (2002)

    CAS  Google Scholar 

  15. A. Natansohn, P. Rochon, Can. J. Chem. 79, 1093 (2001)

    Article  CAS  Google Scholar 

  16. A. Natansohn, P. Rochon, Chem. Rev. 102, 4139 (2002)

    Article  CAS  Google Scholar 

  17. G.S. Kumar, D.C. Neckers, Chem. Rev. 89, 1915 (1989)

    Article  CAS  Google Scholar 

  18. M. Hasegawa, T. Ikawa, M. Tsuchimori, O. Watanabe, J. Appl. Polym. Sci. 86, 17 (2002)

    Article  CAS  Google Scholar 

  19. L.A. Howe, G.D. Jaycox, J. Polym. Sci.: Part A: Polym. Chem 36, 2827 (1998)

    Article  CAS  Google Scholar 

  20. K. Huang, H. Qiu, M. Wan, Macromolecules 35, 8653 (2002)

    Article  CAS  Google Scholar 

  21. S.H.K. Kang, H.-D. Shin, C.H. Oh, D.H. Choi, K.H. Park, Bull. Korean Chem. Soc. 23, 957 (2002)

    Article  CAS  Google Scholar 

  22. P. Uznanski, J. Pecherz, J. Appl. Polym. Sci. 86, 1459 (2002)

    Article  CAS  Google Scholar 

  23. C. Samyn, T. Verbiest, A. Persoons, Macromol. Rapid Commun. 21, 1 (2000)

    Article  CAS  Google Scholar 

  24. G. Iftime, F.L. Labarthet, A. Natansohn, P. Rochon, K. Murti, Chem. Mater. 14, 168 (2002)

    Article  CAS  Google Scholar 

  25. G.H. Kim, C.D. Keunm, S.J. Kim, L.S. Park, J. Polym. Sci., Part A: Polym. Chem. 37, 3715 (1999)

    Article  CAS  Google Scholar 

  26. K. Tawa, K. Kamada, K. Kiyohara, K. Ohta, D. Yasumatsu, Z. Sekkat, S. Kawata, Macromolecules 34, 8232 (2001)

    Article  CAS  Google Scholar 

  27. L. Wu, X. Tuo, H. Cheng, Z. Chen, X. Wang, Macromolecules 34, 8005 (2001)

    Article  CAS  Google Scholar 

  28. P. Rachon, E. Batalla, A. Natansohn, Appl. Phys. Lett. 66, 136 (1995)

    Article  Google Scholar 

  29. D.Y. Kim, S.K. Tripathy, L. Li, J. Kumar, Appl. Phys. Lett. 66, 1166 (1995)

    Article  CAS  Google Scholar 

  30. Z. Wang, H. Tian, K. Chen, Dyes Pigm. 51, 161 (2001)

    Article  CAS  Google Scholar 

  31. C. Lambert, W. Gaschler, M. Zabel, R. Matschiner, R. Wortmann, J. Organomet. Chem. 592, 109 (1999)

    Article  CAS  Google Scholar 

  32. A.M. Breul, M.D. Hager, U.S. Schubert, Chem. Soc. Rev. 42, 5366 (2013)

    Article  CAS  Google Scholar 

  33. A.S. Abd-El-Aziz, T.H. Afifi, W.R. Budakowski, K.J. Friesen, E.K. Todd, Macromolecules 35, 8929 (2002)

    Article  CAS  Google Scholar 

  34. A.S. Abd-El-Aziz, N.M. Pereira, W. Boraie, E.K. Todd, T.H. Afifi, W.R. Budakowski, K.J. Friesen, J. Inorg. Organomet. Polym Mater. 15, 497 (2005)

    Article  CAS  Google Scholar 

  35. A.S. Abd-El-Aziz, E.K. Todd, R.M. Okasha, T.H. Afifi, M. Salih, Macromol. Symp. 196, 89 (2003)

    Article  CAS  Google Scholar 

  36. K.J. Ivin, J.C. Mol, Olefin Metathesis and Metathesis Polymerization (Academic Press, San Diego, 1997)

    Google Scholar 

  37. V. Dragutan, R. Streck, Catalytic Polymerization of Cycloolefins: Ionic, Ziegler-natta and Ring-opening Metathesis Polymerization (Elsevier, Amsterdam, 2000)

    Google Scholar 

  38. T.J. Boyd, R.R. Schrock, Macromolecules 32, 6608 (1999)

    Article  CAS  Google Scholar 

  39. T.J. Boyd, Y. Geerts, J.-K. Lee, D.E. Fogg, G.G. Lavoie, R.R. Schrock, M.F. Rubner, Macromolecules 30, 3553 (1997)

    Article  CAS  Google Scholar 

  40. H.D.M. Maynard, S.Y. Okada, R.H. Grubbs, J. Am. Chem. Soc. 123, 1275 (2001)

    Article  CAS  Google Scholar 

  41. A.S. Abd-El-Aziz, R.M. Okasha, T.H. Afifi, E.K. Todd, Macromol. Chem. Phys. 204, 555 (2003)

    Article  CAS  Google Scholar 

  42. A.S. Abd-El-Aziz, R.M. Okasha, T.H. Afifi, J. Inorg. Organomet. Polym. 14, 269 (2004)

    Article  CAS  Google Scholar 

  43. A.S. Abd-El-Aziz, R.M. Okasha, P.O. Shipman, T.H. Afifi, Macromol. Rapid Commun. 25, 1497 (2004)

    Article  CAS  Google Scholar 

  44. A.S. Abd-El-Aziz, R.M. Okasha, E.K. Todd, T.H. Afifi, P.O. Shipman, K.M.D. Copping, Macromol. Symp. 209, 185 (2004)

    Article  CAS  Google Scholar 

  45. A.S. Abd-El-Aziz, P.O. Shipman, E.G. Neeland, T.C. Corkery, S. Mohammed, P.D. Harvey, H.M. Mohamed, A.H. Bedair, A.M. El-Agrody, P.M. Aguiar, S. Kroeker, Macromol. Chem. Phys. 208, 84 (2008)

    Article  Google Scholar 

  46. A.S. Abd-El-Aziz, E.A. Strohm, M. Ding, R.M. Okasha, T.H. Afifi, S. Sezgin, P.R. Shipley, J. Inorg. Organomet. Polym Mater. 20, 592 (2010)

    Article  CAS  Google Scholar 

  47. W.-Y. Wong, A.S. Abd-El-Aziz (eds.), Molecular Design and Applications of Photofunctional Polymers and Materials (RSC Publishing, Cambridge, 2012)

    Google Scholar 

  48. A.S.A.S. Abd-El-Aziz, E.A. Strohm, Transition metal-containing macromolecules: en route to new functional Materials. Polymer 53, 4879–4921 (2012)

    Article  CAS  Google Scholar 

  49. J.M.J. Fréchet, Science 263, 1710 (1994)

    Article  Google Scholar 

  50. A.S. Abd-El-Aziz, S.A. Carruthers, E.K. Todd, T.H. Afifi, J.M.A. Gavina, J. Polym. Sci., Part A: Polym. Chem. 43, 1382 (2005)

    Article  CAS  Google Scholar 

  51. X. Shen, H. Liu, Y. Li, S. Liu, Macromolecules 41, 2421 (2008)

    Article  CAS  Google Scholar 

  52. T. Tuuttila, J. Lipsonen, M. Lahtinen, J. Huuskonen, K. Rissanen, Tetrahedron 64, 10590 (2008)

    Article  CAS  Google Scholar 

  53. A.O. Moughton, R.K. O’Reilly, Macromol. Rapid Commun. 31, 37 (2010)

    Article  CAS  Google Scholar 

  54. P. Rempp, J.E. Herz, Encyclopedia of Polymer Science and Engineering, vol. 793, 2nd edn. (Wiley, New York, 1989)

    Google Scholar 

  55. T.H. Higashihara, K. Sugiyama, H.S. Yoo, M. Hayashi, A. Hirao, Macromol. Rapid Commun. 31, 1031 (2010)

    Article  CAS  Google Scholar 

  56. A.S. Abd-El-Aziz, P.O. Shipman, B.N. Boden, W.S. McNeil, Prog. Polym. Sci. 35, 714 (2010)

    Article  CAS  Google Scholar 

  57. S. Wang, X. Wang, L. Li, R.C. Advincula, J. Org. Chem. 69, 9073 (2004)

    Article  CAS  Google Scholar 

  58. H. Deligo¨z, J. Inclusion Phenom. Macrocyclic Chem 55, 197 (2006)

    Article  Google Scholar 

  59. C.D. Gutsche, L. Lin, Tetrahedron 42, 1633 (1986)

    Article  CAS  Google Scholar 

  60. M.A. McKervey, E.M. Seward, G. Ferguson, B.L. Ruhl, J. Org. Chem. 51, 3581 (1986)

    Article  CAS  Google Scholar 

  61. S. Shinkai, H. Koreishi, K. Ueda, T. Arimura, O. Manabe, J. Am. Chem. Soc. 109, 6371 (1987)

    Article  CAS  Google Scholar 

  62. J. Zeller, S. Koenig, U. Radius, Inorg. Chim. Acta 357, 1813 (2004)

    Article  CAS  Google Scholar 

  63. M.T. Blanda, E. Adou, Polymer 39, 3821 (1998)

    Article  CAS  Google Scholar 

  64. G. Podoprygorina, M. Janke, A. Janshoff, V. Bo¨hmer. Supramol. Chem. 20, 59 (2008)

    Article  CAS  Google Scholar 

  65. Y. Yang, T.M. Swager, Macromolecules 40, 7437 (2007)

    Article  CAS  Google Scholar 

  66. Y. Yang, T.M. Swager, Macromolecules 39, 2013 (2006)

    Article  CAS  Google Scholar 

  67. K. Chang, I. Su, G. Lee, W. Chung, Tetrahedron Lett. 48, 7274 (2007)

    Article  CAS  Google Scholar 

  68. A.S. Abd-El-Aziz, P.O. Shipman, J.L. Pilfold, P.R. Shipley, Macromol. Chem. Phys. 211, 996 (2010)

    Article  CAS  Google Scholar 

  69. A.S. Abd-El-Aziz, P.O. Shipman, J.L. Pilfold, P.R. Shipley, Macromol. Rapid Commun. 33, 459 (2010)

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Taibah University, Madinah, Saudi Arabia

    Rawda M. Okasha

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Correspondence to Rawda M. Okasha.

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This review article is dedicated to the memory of Professor E.W. Neuse for his outstanding contribution to the field of organometallic polymers.

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Okasha, R.M. Proton Sensing Color Changing Organoiron and Organic Macromolecules. J Inorg Organomet Polym 25, 354–366 (2015). https://doi.org/10.1007/s10904-015-0193-6

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