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Organometallic and Coordination Polymers, and Linear and Star Oligomers Using the trans-Pt(PR3)2(C≡C)2 Linker

Article

Abstract

This review article presents the advances made by the Harvey group over the past 10 years on the development of new functional materials using the trans-Pt(PR3)2(C≡C)2 fragment, [Pt], mainly targeting photonic properties. The presented topics include the synthesis, electronic communication across the chain, polymers bearing chiral P-centers, electroactive polymers, photo-induced electron transfers, triplet excited state energy transfers, formation of charge transfer excited states for push–pull polymers, trans-Pt(PR3)2(C≡C)2-containing polyaniline, star molecules and coordination polymers. This research aims at designing photonic devices, such as solar cells and light emitting diodes, and evaluating their performances, as well as sensors for gases, namely CO2, and small molecules. The photophysical properties of the related trans-(C≡C)Pt(dppm)2Pt(C≡C) fragment ([Pt 2 ]) is presented for comparison purposes. It turns out that the Pt(I)–Pt(I) bond is excellent for electronic communication but is also particularly sensitive to oxidative additions, hence limiting its applications.

Graphical Abstract

Keywords

Platinum Organometallic polymer Synthesis Energy transfer Electron transfer Sensor Coordination polymer Star molecule 

General codes employed in this review article

[Pt]

Trans-Pt(PR3)2(C≡C)2 linker

[Pt2]

(C≡C)Pt(dppm)2Pt(C≡C) linker

P x

Polymer species

Model x

Model compound

Ox

Oligomer species

CP x

Coordination polymer

SM x

Star molecule

[Zn]

Zinc(II)porphyrin dye

[Ir]

Bis(2,2′-bipyridyl)-2-(phenylpyridine)iridium(III) unit

Cycle x

Cyclic product

dyad x

Donor–acceptor

Notes

Acknowledgements

The NSERC, Natural Sciences and Engineering Research Council of Canada, the FRQNT, Fonds de Recherche du Québec – Nature et Technologies, the CQMF, Centre Québéquois des Matériaux Fonctionnels, and the CEMOPUS, Centre d’Études des Matériaux Optiques et Photoniques de l’Université de Sherbrooke are thanked for their financial support. PDH is also indebted to the Agence nationale de la recherche (ANR) for a Research Chair of Excellence while in Dijon (2008–2010). The author would also like to express his deepest gratitude towards collaborators and friends (in no particular order: Prof. Wai-Yeung Wong, Prof. Roger Guilard, Prof. Claude Gros, Prof. Sylvain Jugé, Prof. Michael Knorr, Prof. Eli Zysman-Colman, Prof. Gessie Brisard, Prof. Armand Soldera, Prof. Alaa S. Abd-El-Aziz, Prof. William Geiger, Dr. Daniel Fortin and Mr. Paul-Ludovic Karsenti) and all the students and postdoctoral fellows for their valuable contributions with this research program. Their names appear in the list of references.

References

  1. 1.
    J. Chatt, B.L. Shaw, J. Chem. Soc. 4020–4033 (1959)Google Scholar
  2. 2.
    M.I. Bruce, D.A. Harbourne, F. Waugh, F.G.A. Stone, J. Chem. Soc. A. (1968). doi: 10.1039/J19680000356 Google Scholar
  3. 3.
    I. Collamati, A. Furlani, J. Organomet. Chem. 17, 457–461 (1969)CrossRefGoogle Scholar
  4. 4.
    K. Sonogashira, S. Kataoka, S. Takahashi, N. Hagihara. J. Organomet. Chem. 160, 319–327 (1978)CrossRefGoogle Scholar
  5. 5.
    S. Takahashi, Y. Ohyama, E. Murata, K. Sonogashira, N. Hagihara, J. Polym. Sci. 18, 349–353 (1980)Google Scholar
  6. 6.
    G.-J. Zhou, W.-Y. Wong, Chem. Soc. Rev. 40, 2541–2566 (2011)CrossRefGoogle Scholar
  7. 7.
    J. Mei, K. Ogawa, Y.-G. Kim, N.C. Heston, D.J. Arenas, Z. Nasrollahi, T.D. McCarley, D.B. Tanner, J.R. Reynolds, K.S. Schanze, ACS Appl. Mater. Interfaces 1, 150–161 (2009)CrossRefGoogle Scholar
  8. 8.
    A.H. Shelton, R.S. Price, L. Brokmann, B. Dettlaff, K.S. Schanze, ACS Appl. Mater. Interfaces 5, 7867–7874 (2013)CrossRefGoogle Scholar
  9. 9.
    L. Sudha Devi, M.K. Al-Suti, N. Zhang, S.J. Teat, L. Male, H.A. Sparkes, P.R. Raithby, M.S. Khan, A. Köhler, Macromolecules 42, 1131–1141 (2009)CrossRefGoogle Scholar
  10. 10.
    C.L. Ho, Z.Q. Yu, W.-Y. Wong, Chem. Soc. Rev. 45, 5264–5295 (2016)CrossRefGoogle Scholar
  11. 11.
    J. Xiang, C.L. Ho, W.-Y. Wong, Polym. Chem. 6, 6905–6930 (2015)CrossRefGoogle Scholar
  12. 12.
    L. Ying, C.-L. Ho, H. Wu, Y. Cao, W.-Y. Wong, Adv. Mater. 26, 2459–2473 (2014)CrossRefGoogle Scholar
  13. 13.
    X. Yang, G. Zhou, W.-Y. Wong, J. Mater. Chem. C 2, 1760–1778 (2014)CrossRefGoogle Scholar
  14. 14.
    C.-L. Ho, W.-Y. Wong, in Molecular Design and Applications of Photofunctional Polymers and Materials. Royal Society of Chemistry Polymer Chemistry Series (2012), pp. 1–30Google Scholar
  15. 15.
    C.-L. Ho, W.-Y. Wong, Coord. Chem. Rev. 257, 1614–1649 (2013)CrossRefGoogle Scholar
  16. 16.
    C.-L. Ho, W.-Y. Wong, Coord. Chem. Rev. 255, 2469–2502 (2011)CrossRefGoogle Scholar
  17. 17.
    W.-Y. Wong, C.-L. Ho, Acc. Chem. Res. 43, 1246–1256 (2010)CrossRefGoogle Scholar
  18. 18.
    W.-Y. Wong, P.D. Harvey, Macromol. Rapid Commun. 31, 671–713 (2010)CrossRefGoogle Scholar
  19. 19.
    A. Sebald, B. Wrackmeyer, W.Z. Beck, Naturforsch 38B, 45–56 (1983)Google Scholar
  20. 20.
    X. Wang, D. Fortin, G. Brisard, P.D. Harvey, Macromol. Rapid Commun. 35, 992–997 (2014)CrossRefGoogle Scholar
  21. 21.
    K. Gagnon, S.M. Aly, A. Brisach-Wittmeyer, D. Bellows, J.-F. Berube, L. Caron, A.S. Abd-El-Aziz, D. Fortin, P.D. Harvey, Organometallics 27, 2201–2214 (2008)CrossRefGoogle Scholar
  22. 22.
    D. Fortin, S. Clement, K. Gagnon, J.-F. Berube, M.P. Stewart, W.E. Geiger, P.D. Harvey, Inorg. Chem. 48, 446–454 (2009)CrossRefGoogle Scholar
  23. 23.
    F.L. Jiang, D. Fortin, P.D. Harvey, Inorg. Chem. 49, 2614–2623 (2010)CrossRefGoogle Scholar
  24. 24.
    A.M. Soliman, E. Zysman-Colman, P.D. Harvey, Macromol. Rapid Commun. 36, 627–632 (2015)CrossRefGoogle Scholar
  25. 25.
    M. Turcotte, P.D. Harvey, Inorg. Chem. 41, 2971–2974 (2002)CrossRefGoogle Scholar
  26. 26.
    D. Bellows, S.M. Aly, C.P. Gros, M. El Ojaimi, J.-M. Barbe, R. Guilard, P.D. Harvey, Inorg. Chem. 48, 7613–7629 (2009)CrossRefGoogle Scholar
  27. 27.
    G. Langlois, S.M. Aly, C.P. Gros, J.-M. Barbe, P.D. Harvey, New J. Chem. 35, 1302–1314 (2011)CrossRefGoogle Scholar
  28. 28.
    X. Wang, D. Fortin, G. Brisard, P.D. Harvey, Chem. Commun. 50, 350–352 (2014)CrossRefGoogle Scholar
  29. 29.
    A. Lapprand, N. Khiri, D. Fortin, S. Juge, P.D. Harvey, Inorg. Chem. 52, 2361–2371 (2013)CrossRefGoogle Scholar
  30. 30.
    F. Chaux, S. Frynas, H. Laureano, C. Salomon, G. Morata, M.-L. Auclair, M. Stephan, R. Merdes, P. Richard, M.-J. Ondel-Eymin, J.C. Hendry, J. Bayardon, C. Darcel, S. Juge, C. R. Chim. 12, 1213–1226 (2010)CrossRefGoogle Scholar
  31. 31.
    B.M. Squeo, V.G. Gregoriou, A. Avgeropoulos, S. Baysec, S. Allard, U. Scherf, C.L. Chochos, Prog. Polym. Sci. 71, 26–52 (2017)CrossRefGoogle Scholar
  32. 32.
    L. Bucher, S.M. Aly, N. Desbois, P.-L. Karsenti, C.P. Gros, P.D. Harvey, J. Phys. Chem. C 121, 6478–6491 (2017)CrossRefGoogle Scholar
  33. 33.
    L. Fu, F.-L. Jiang, D. Fortin, P.D. Harvey, Y. Liu, Chem. Commun. 47, 5503–5505 (2011)CrossRefGoogle Scholar
  34. 34.
    H. Jia, B. Kucukoz, Y. Xing, P. Majumdar, C. Zhang, A. Karatay, G. Yaglioglu, A. Elmali, J. Zhao, M. Hayvali, J. Mater. Chem. C 2, 9720–9736 (2014)CrossRefGoogle Scholar
  35. 35.
    W. Yang, A. Karatay, J. Zhao, J. Song, L. Zhao, Y. Xing, C. Zhang, C. He, H.G. Yaglioglu, M. Hayvali, A. Elmali, B. Kucukoz, Inorg. Chem. 54, 7492–7505 (2015)CrossRefGoogle Scholar
  36. 36.
    M.-H. Nguyen, J.H.K. Yip, Organometallics 31, 7522–7531 (2012)CrossRefGoogle Scholar
  37. 37.
    M.-H. Nguyen, J.H.K. Yip, Organometallics 30, 6383–6392 (2011)CrossRefGoogle Scholar
  38. 38.
    M.-H. Nguyen, V.H. Nguyen, J.H.K. Yip, Organometallics 32, 7283–7291 (2013)CrossRefGoogle Scholar
  39. 39.
    A. Bonnot, P.D. Harvey, J. Inorg. Organomet. Polym. Mater. 26, 1328–1337 (2016)CrossRefGoogle Scholar
  40. 40.
    A.M. Soliman, M. Abdelhameed, E. Zysman-Colman, P.D. Harvey, Chem. Commun. 49, 5544–5546 (2013)CrossRefGoogle Scholar
  41. 41.
    S. Clement, T. Goudreault, D. Bellows, D. Fortin, L. Guyard, M. Knorr, P.D. Harvey, Chem. Commun. 48, 8640–8642 (2012)CrossRefGoogle Scholar
  42. 42.
    D. Osella, R. Gobetto, C. Nervi, M. Ravera, R. D’Amato, M.V. Russo, Inorg. Chem. Commun. 1, 239–245 (1998)CrossRefGoogle Scholar
  43. 43.
    T. Nishiumi, Y. Chimoto, Y. Hagiwara, M. Higushi, K. Yamamoto, Macromolecules 37, 2661–2664 (2004)CrossRefGoogle Scholar
  44. 44.
    X. Wang, T. Kenny, D. Fortin, S.M. Aly, G. Brisard, P.D. Harvey, Organometallics 34, 1567–1581 (2015)CrossRefGoogle Scholar
  45. 45.
    S.M. Aly, C.-L. Ho, D. Fortin, W.-Y. Wong, A.S. Abd-El-Aziz, P.D. Harvey, Chem. Eur. J. 14, 8341–8352 (2008)CrossRefGoogle Scholar
  46. 46.
    S.M. Aly, C.-L. Ho, W.-Y. Wong, D. Fortin, P.D. Harvey, Macromolecules 42, 6902–6916 (2009)CrossRefGoogle Scholar
  47. 47.
    T. Forster, Ann. Phys. 2, 55–80 (1948)CrossRefGoogle Scholar
  48. 48.
    D.L. Dexter, J. Chem. Phys. 21, 836–850 (1953)CrossRefGoogle Scholar
  49. 49.
    A. Langlois, P.D. Harvey, J. Porph. Phthalocyanines 18, 666–674 (2014)CrossRefGoogle Scholar
  50. 50.
    S. Faure, C. Stern, R. Guilard, P.D. Harvey, J. Am. Chem. Soc. 126, 1253–1261 (2004)CrossRefGoogle Scholar
  51. 51.
    P.D. Harvey, in Porphyrin Handbook, 18, ed. by K. M. Kadish, K. M. Smith, R. Guilard eds. (Academic Press, Paris, 2003), pp. 63–250CrossRefGoogle Scholar
  52. 52.
    B. Du, P.D. Harvey, Chem. Commun. 48, 2671–2673 (2012)CrossRefGoogle Scholar
  53. 53.
    B. Du, D. Fortin, P.D. Harvey, J. Inorg. Organomet. Polym. Mater. 23, 81–88 (2013)CrossRefGoogle Scholar
  54. 54.
    A.M. Soliman, D. Fortin, E. Zysman-Colman, P.D. Harvey, Chem. Commun. 48, 6271–6273 (2012)CrossRefGoogle Scholar
  55. 55.
    J.-M. Camus, S.M. Aly, C. Stern, R. Guilard, P.D. Harvey, Chem. Commun. 47, 8817–8819 (2011)CrossRefGoogle Scholar
  56. 56.
    L. Liu, D. Fortin, P.D. Harvey, Inorg. Chem. 48, 5891–5900 (2009)CrossRefGoogle Scholar
  57. 57.
    A. Langlois, J.-M. Camus, P.-L. Karsenti, R. Guilard, P.D. Harvey, Inorg. Chem. 56, 2506–2517 (2017)CrossRefGoogle Scholar
  58. 58.
    P.D. Harvey, B. Daoust, Can. J. Chem 70, 2777–2784 (1992)CrossRefGoogle Scholar
  59. 59.
    T. Kenny, S.M. Aly, G. Brisard, D. Fortin, P.D. Harvey, Macromol. Rapid Commun. 34, 511–515 (2013)CrossRefGoogle Scholar
  60. 60.
    A.M. Soliman, D. Fortin, P.D. Harvey, E. Zysman-Colman, Chem. Commun. 48, 1120–1122 (2012)CrossRefGoogle Scholar
  61. 61.
    T. Kenny, S. Lamare, S.M. Aly, D. Fortin, G. Brisard, P.D. Harvey, Inorg. Chem. 51, 13081–13095 (2012)CrossRefGoogle Scholar
  62. 62.
    S.M. Aly, T. Kenny, S. Lamare, P.D. Harvey, J. Inorg. Organomet. Polym. Mater. 25, 118–125 (2015)CrossRefGoogle Scholar
  63. 63.
    K. Gagnon, S.M. Aly, D. Fortin, A.S. Abd-El-Aziz, P.D. Harvey, J. Inorg. Organomet. Polym. Mater. 19, 28–34 (2009)CrossRefGoogle Scholar
  64. 64.
    T. Kenny, S.M. Aly, D. Fortin, P.D. Harvey, Chem. Commun. 48, 11543–11545 (2012)CrossRefGoogle Scholar
  65. 65.
    C.-H. Siu, L.T.L. Lee, S.-C. Yiu, P.-Y. Ho, P. Zhou, C.-L. Ho, T. Chen, J. Liu, K. Han, W.-Y. Wong, ‎Chem. Eur. J. 22, 3750–3757 (2016)CrossRefGoogle Scholar
  66. 66.
    W. Wu, Z.-Y. Li, Z. Zheng, Y. Hu, J. Hua, Dyes Pigments 111, 21–29 (2014)CrossRefGoogle Scholar
  67. 67.
    A. Tigreros, V. Dhas, A. Ortiz, B. Insuasty, N. Martin, L. Echegoyen, Sol. Energy Mater. Sol. Cells 121, 61–68 (2014)CrossRefGoogle Scholar
  68. 68.
    Z.-Y. Li, W. Wu, Q. Zhang, B. Jin, J. Hua, H.-B. Yang, H. Tian, Chem. Asian J. 8, 2660–2669 (2013)CrossRefGoogle Scholar
  69. 69.
    F.-R. Dai, Y.-C. Chen, L.-F. Lai, W.-J. Wu, C.-H. Cui, G.-P. Tan, X.-Z. Wang, J.-T. Lin, H. Tian, W.-Y. Wong, Chem. Asian J. 7, 1426–1434 (2012)CrossRefGoogle Scholar
  70. 70.
    W. Wu, J. Zhang, H. Yang, B. Jin, Y. Hu, J. Hua, C. Jing, Y. Long, H. Tian, J. Mater. Chem. 22, 5382–5389 (2012)CrossRefGoogle Scholar
  71. 71.
    W. Wu, X. Xu, H. Yang, J. Hua, X. Zhang, L. Zhang, Y. Long, H. Tian, J. Mater. Chem. 21, 10666–10671 (2011)CrossRefGoogle Scholar
  72. 72.
    P. Luo, P.-L. Karsenti, G. Brisard, B. Marsan, P.D. Harvey, Chem. Commun. 51, 17305–17308 (2015)CrossRefGoogle Scholar
  73. 73.
    P. Luo, P.-L. Karsenti, G. Brisard, B. Marsan, P.D. Harvey, Inorg. Chem. 55, 1894–1904 (2016)CrossRefGoogle Scholar
  74. 74.
    P. Luo, P.-L. Karsenti, G. Brisard, B. Marsan, P.D. Harvey, Organometallics 35, 816–826 (2016)CrossRefGoogle Scholar
  75. 75.
    L. Liu, L. Hu, H. Fu, Q.-M. Fu, S.-Z. Liu, Z.-L. Du, W.-Y. Wong, P.D. Harvey, J. Organomet. Chem. 696, 1319–1324 (2011)CrossRefGoogle Scholar
  76. 76.
    H. Zhan, S. Lamare, A. Ng, T. Kenny, H. Guernon, W.-K. Chan, A.B. Djurisic, P.D. Harvey, W.-Y. Wong, Macromolecules 44, 5155–5167 (2011)CrossRefGoogle Scholar
  77. 77.
    D. Gao, S.M. Aly, P.-L. Karsenti, G. Brisard, P.D. Harvey, Phys. Chem. Chem. Phys. (2017). doi: 10.1039/c7cp04193d Google Scholar
  78. 78.
    C.-L. Ho, C.-H. Chui, W.-Y. Wong, S.M. Aly, D. Fortin, P.D. Harvey, B. Yao, Z. Xie, L. Wang, Macromol. Chem. Phys. 210, 1786–1798 (2009)CrossRefGoogle Scholar
  79. 79.
    T. Goudreault, Z. He, Y. Guo, C.-L. Ho, H. Zhan, Q. Wang, K.Y.-F. Ho, K.-L. Wong, D. Fortin, B. Yao, Z. Xie, L. Wang, W.-M. Kwok, P.D. Harvey, W.-Y. Wong, Macromolecules 43, 7936–7949 (2010)CrossRefGoogle Scholar
  80. 80.
    H. Lang, A. Del Villar, B. Walfort, G. Rheinwald, J. Organomet. Chem. 689, 1464–1471 (2004)CrossRefGoogle Scholar
  81. 81.
    H. Lang, A. Del Villar, B. Walfort, Inorg. Chem. Commun. 7, 694–697 (2004)CrossRefGoogle Scholar
  82. 82.
    F. Juvenal, A. Langlois, A. Bonnot, D. Fortin, P.D. Harvey, Inorg. Chem. 55, 11096–11109 (2016)CrossRefGoogle Scholar
  83. 83.
    F. Juvenal, A. Bonnot, D. Fortin, P.D. Harvey, ACS Omega (2017) (submitted)Google Scholar
  84. 84.
    C.K.M. Chan, C.-H. Tao, H.-L. Tam, N. Zhu, K.-W. Yam, Vivian,, Cheah, Inorg. Chem. 48, 2855–2864 (2009)CrossRefGoogle Scholar
  85. 85.
    C.-C. Huang, Y.-C. Lin, P.-Y. Lin, Y.-J. Chen, Eur. J. Org. Chem. 2006, 4510–4518 (2006)CrossRefGoogle Scholar
  86. 86.
    G. Vives, A. Carella, J.-P. Launay, G. Rapenne, Chem. Commun. 21, 2283–2285 (2006)CrossRefGoogle Scholar
  87. 87.
    H. Lei, A. Langlois, D. Fortin, P.-L. Karsenti, S.M. Aly, P.D. Harvey, Phys. Chem. Chem. Phys. 19, 21532-21539 (2017)CrossRefGoogle Scholar
  88. 88.
    H. Lei, S.M. Aly, P.-L. Karsenti, D. Fortin, P.D. Harvey, Organometallics 36, 572–581 (2017)CrossRefGoogle Scholar
  89. 89.
    H. Lei, S.M. Aly, P.-L. Karsenti, D. Fortin, P.D. Harvey, Inorg. Chem. (2017) (submitted)Google Scholar
  90. 90.
    C.R. Langrick, P.G. Pringle, B.L. Shaw, J. Chem. Soc. Dalton Trans. 5, 1015–1017 (1985)CrossRefGoogle Scholar
  91. 91.
    J.H.K. Yip, J. Wu, K.-Y. Wong, K.P. Ho, C.S.-N. Pun, J.J. Vittal, Organometallics 21, 5292–5300 (2002)CrossRefGoogle Scholar
  92. 92.
    D. Bellows, T. Goudreault, S.M. Aly, D. Fortin, C.P. Gros, J.-M. Barbe, P.D. Harvey, Organometallics 29, 317–325 (2010)CrossRefGoogle Scholar
  93. 93.
    M.J. Irwin, G. Jia, J.J. Vittal, R.J. Puddephatt, Organometallics 15, 5321–5329 (1996)CrossRefGoogle Scholar
  94. 94.
    S. Clément, S.M. Aly, D. Bellows, D. Fortin, C. Strohmann, L. Guyard, A.S. Abd-El-Aziz, M. Knorr, P.D. Harvey, Inorg. Chem. 48, 4118–4133 (2009)CrossRefGoogle Scholar
  95. 95.
    J.-F. Bérubé, K. Gagnon, D. Fortin, A. Decken, P.D. Harvey, Inorg. Chem. 45, 2812–2823 (2006)CrossRefGoogle Scholar
  96. 96.
    S. Clément, S.M. Aly, K. Gagnon, A.S. Abd-El-Aziz, M. Knorr, P.D. Harvey, J. Inorg. Organomet. Chem. Mater. 18, 104–110 (2008)CrossRefGoogle Scholar
  97. 97.
    S. Clément, S.M. Aly, J. Husson, M. Knorr, L. Guyard, A.S. Abd-El-Aziz, P.D. Harvey, Eur. J. Inorg. Chem. 2009, 2536–2546 (2009)CrossRefGoogle Scholar
  98. 98.
    S. Clément, S.M. Aly, D. Fortin, L. Guyard, M. Knorr, A.S. Abd-El-Aziz, P.D. Harvey, Inorg. Chem. 47, 10816–10824 (2008)CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  1. 1.Département de chimieUniversité de SherbrookeSherbrookeCanada

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