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Pentacene- and BODIPY-Containing trans-Bis(ethynyl)bis(phosphine)platinum(II) Organometallic Polymers: A DFT Point of View

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Abstract

The effect of the polymer dimension and the nature of the end-group of oligomer models containing pentacence ([pen]) and BODIPY ([BOD]) alternating with the organometallic fragment trans-bis(trialkylphosphine)platinum(II) ([Pt]), i.e. ([Ar] n–[Pt] m)x with [Ar] = C≡C–[pen]–C≡C, C≡C–[BOD]–C≡C, and 1 < x < 4, on their structures and optical properties were investigated by means of DFT and TDDFT (B3LYP) calculations. For sake of reduction of computation size for the oligomers, the trialkylphosphine was set to PMe3 instead of the commonly encountered PBu3 in the experimental articles. Two specific aspects were addressed. Firstly, a series of computations were performed in a systematic manner in order to find the best conditions for these calculations (namely the choice of basis sets and solvent fields), due to the large size of the oligomer models. Secondly, the effect of the oligomer size and nature of the terminal unit of ([Ar] n–[Pt] m)x, namely C≡C–[pen]–C≡CH or C≡C–[BOD]–C≡CH and [Pt]–Cl, on the structure and electronic properties have also been examined. These calculations indicate that the nature of end-groups has a little impact on the properties mentioned above for the alternating ((C≡C–[BOD]–C≡C) n–[Pt] m)x oligomers, but some minor effects are noted for the (C≡C–[pen]–C≡C)-containing species. Noteworthy, the evolution of the properties, notably the position of the lowest energy electronic transition, shows no significant evolution above 3 units. This computational result indicates the limitation of the electronic communication across the polymer chains. The lowest energy electronic states are all mainly ππ* located in the [Ar] fragment. Consequently, this work was limited to 4 units only.

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References

  1. W.-Y. Wong, P.D. Harvey, Macromol. Rapid. Commun. 31, 671–713 (2010)

    Article  CAS  Google Scholar 

  2. 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)

    Article  CAS  Google Scholar 

  3. A.A.I. Sina, S.M.I. Al-Rafia, MdF Ahmad, R.K. Paul, S.M.S. Islam, M. Younus, P.R. Raithby, C.-L. Ho, Y.H. Lo, L. Liu, H. Li, W.-Y. Wong, J. Inorg. Organomet. Polym. Mater. 25, 427–436 (2015)

    CAS  Google Scholar 

  4. C.-L. Ho, S.-Y. Poon, P.-K. Lo, M.-S. Wong, W.-Y. Wong, J. Inorg. Organomet. Polym. Mater. 23, 206–215 (2013)

    Article  CAS  Google Scholar 

  5. F.R.F. 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)

    Article  CAS  Google Scholar 

  6. L. Li, C.-L. Ho, W.-Y. Wong, J. Organomet. Chem. 703, 43–50 (2012)

    Article  CAS  Google Scholar 

  7. F.-R. Dai, H.-M. Zhan, Q. Liu, Y.-Y. Fu, J.-H. Li, Q.-W. Wang, Z. Xie, L. Wang, F. Yan, W.-Y. Wong, Chem. Euro. J. 18, 1502–1511 (2012)

    Article  CAS  Google Scholar 

  8. H. Zhan, W.-Y. Wong, A. Ng, A.B. Djurisic, W.-K. Chan, J. Organomet. Chem. 696, 4112–4120 (2011)

    Article  CAS  Google Scholar 

  9. Q. Wang, Z. He, A. Wild, H. Wu, Y. Cao, U.S. Schubert, C.-H. Chui, W.-Y. Wong, Chem. Asian. J. 6, 1766–1777 (2011)

    Article  CAS  Google Scholar 

  10. L. Li, W.-C. Chow, W.-Y. Wong, C.-H. Chui, R.S.-M. Wong, J. Organomet. Chem. 696, 1189–1197 (2011)

    Article  CAS  Google Scholar 

  11. Q. Wang, W.-Y. Wong, Poly. Chem. 2, 432–440 (2011)

    Article  CAS  Google Scholar 

  12. C. Qin, W.-Y. Wong, L. Wang, Macromolecules 44, 483–489 (2011)

    Article  CAS  Google Scholar 

  13. X.-Z. Wang, C.-L. Ho, L. Yan, X. Chen, X. Chen, K.-Y. Cheung, W.-Y. Wong, J. Inorg. Organomet. Polym. Mater. 20, 478–487 (2010)

    Article  CAS  Google Scholar 

  14. X.-Z. Wang, Q. Wang, L. Yan, W.-Y. Wong, K.-Y. Cheung, A. Ng, A.B. Djurisic, W.-K. Chan, Macromol. Rapid. Commun. 31, 861–867 (2010)

    Article  CAS  Google Scholar 

  15. H.-M. 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)

    Article  CAS  Google Scholar 

  16. T. Goudreault, Z. He, Y. Guo, C.-L. Ho, H. Zhan, H. Qiwei, Y.-F. Keith, 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)

    Article  CAS  Google Scholar 

  17. 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)

    Article  CAS  Google Scholar 

  18. S.M. Aly, C.-L. Ho, W.-Y. Wong, D. Fortin, P.D. Harvey, Macromolecules 42, 6902–6916 (2009)

    Article  CAS  Google Scholar 

  19. S.M. Aly, C.-L. Ho, D. Fortin, W.-Y. Wong, A.S. Abd-El-Aziz, P.D. Harvey, Chem. Euro. J. 14, 8341–8352 (2008)

    Article  CAS  Google Scholar 

  20. X. Wang, T. Kenny, D. Fortin, S.M. Aly, G. Brisard, P.D. Harvey, Organometallics 34, 1567–1581 (2015)

    Article  CAS  Google Scholar 

  21. A.M. Soliman, E. Zysman-Colman, P.D. Harvey, Macromol. Rapid. Commun. 36, 627–632 (2015)

    Article  CAS  Google Scholar 

  22. X. Wang, D. Fortin, G. Brisard, P.D. Harvey, Macromol. Rapid. Commun. 35, 992–997 (2014)

    Article  CAS  Google Scholar 

  23. X. Wang, D. Fortin, G. Brisard, P.D. Harvey, Chem. Commun. 50, 350–352 (2014)

    Article  CAS  Google Scholar 

  24. S. Clement, T. Goudreault, D. Bellows, D. Fortin, L. Guyard, M. Knorr, P.D. Harvey, Chem. Commun. 48, 8640–8642 (2012)

    Article  CAS  Google Scholar 

  25. A.M. Soliman, D. Fortin, E. Zysman-Colman, P.D. Harvey, Chem. Commun. 48, 6271–6273 (2012)

    Article  CAS  Google Scholar 

  26. A.M. Soliman, D. Fortin, E. Zysman-Colman, P.D. Harvey, Macromol. Rapid. Commun. 33, 522–527 (2012)

    Article  CAS  Google Scholar 

  27. D. Fortin, S. Clement, K. Gagnon, J.-F. Berube, M.P. Stewart, W.E. Geiger, P.D. Harvey, Inorg. Chem. 48, 446–454 (2009)

    Article  CAS  Google Scholar 

  28. 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)

    Article  CAS  Google Scholar 

  29. A. Lapprand, N. Khiri, D. Fortin, S. Juge, P.D. Harvey, Inorg. Chem. 52, 2361–2371 (2013)

    Article  CAS  Google Scholar 

  30. S.M. Aly, T. Kenny, S. Lamare, P.D. Harvey, J. Inorg. Organomet. Polym. Mater. 25, 118–125 (2015)

    Article  CAS  Google Scholar 

  31. T. Kenny, S.M. Aly, G. Brisard, D. Fortin, P.D. Harvey, Macromol. Rapid. Commun. 34, 511–515 (2013)

    Article  CAS  Google Scholar 

  32. B. Du, D. Fortin, P.D. Harvey, J. Inorg. Organomet. Polym. Mater. 23, 81–88 (2013)

    Article  CAS  Google Scholar 

  33. T. Kenny, S. Lamare, S.M. Aly, D. Fortin, G. Brisard, P.D. Harvey, Inorg. Chem. 51, 13081–13095 (2012)

    Article  CAS  Google Scholar 

  34. F.-L. Jiang, D. Fortin, P.D. Harvey, Inorg. Chem. 49, 2614–2623 (2010)

    Article  CAS  Google Scholar 

  35. S. Goswami, G. Wicks, A. Rebane, K.S. Schanze, Dalton Trans. 43, 17721–17728 (2014)

    Article  CAS  Google Scholar 

  36. K. Ogawa, F. Guo, K.S. Schanze, J. Photochem. Photobiol. A. 207, 79–85 (2009)

    Article  CAS  Google Scholar 

  37. 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)

    Article  CAS  Google Scholar 

  38. F. Guo, Y.-G. Kim, J.R. Reynolds, K.S. Schanze, Chem. Commun. 17, 1887–1889 (2006)

    Article  Google Scholar 

  39. K. Haskins-Glusac, M.R. Pinto, C. Tan, K.S. Schanze, J. Am. Chem. Soc. 126, 14964–14971 (2004)

    Article  CAS  Google Scholar 

  40. I. Fratoddi, C. Battocchio, A.L. Groia, M.V. Russo, J. Polym. Sci. Pol. Chem. 45, 3311–3329 (2007)

    Article  CAS  Google Scholar 

  41. L. Sudha Devi, M.K. Al-Suti, N. Zhang, S.J. Teat, L. Male, H.A. Sparkes, P.R. Raithby, M.S. Khan, A. Kohler, Macromolecules 42, 1131–1141 (2009)

    Article  CAS  Google Scholar 

  42. M. Jura, O.F. Koentjoro, P.R. Raithby, E.L. Sharp, P.J. Wilson, Mater. Res. Soc. Symp. Proc. 846, 59–64 (2005)

    CAS  Google Scholar 

  43. M.S. Khan, M.K. Al-Suti, H.H. Shah, S. Al-Humaimi, F.R. Al-Battashi, J.K. Bjernemose, L. Male, P.R. Raithby, N. Zhang, A. Koehler, J.E. Warren, Dalton Trans. 40, 10174–10183 (2011)

    Article  CAS  Google Scholar 

  44. L. Sudha Devi, M.K. Al-Suti, C. Dosche, M.S. Khan, R.H. Friend, A. Kohler, Phys. Rev. B Condens. Matter. 78, 045210–045218 (2008)

    Article  Google Scholar 

  45. W.-Y. Wong, X.-Z. Wang, Z. He, K.-K. Chan, A.B. Djurisic, K.-Y. Cheung, C.-T. Yip, A.M.-C. Ng, Y.Y. Xi, C.S.K. Mak, W.-K. Chan, J. Am. Soc. 129, 14372–14380 (2007)

    Article  CAS  Google Scholar 

  46. X.-Z. Wang, W.-Y. Wong, K.-Y. Cheung, M.-K. Fung, A.B. Djurisic, W.-K. Chan, Dalton Trans. 40, 5484–5494 (2008)

    Article  Google Scholar 

  47. L. Liu, C.-L. Ho, W.-Y. Wong, K.-Y. Cheung, M.-K. Fung, W.-T. Lam, A.B. Djurisic, W.-K. Chan, Adv. Funct. Mater. 18, 2824–2833 (2008)

    Article  CAS  Google Scholar 

  48. W.-Y. Wong, X.-Z. Wang, H.-L. Zhang, K.-Y. Cheung, M.-K. Fung, A.B. Djurisic, W.-K. Chan, J. Organomet. Chem. 693, 3603–3612 (2008)

    Article  CAS  Google Scholar 

  49. W.-Y. Wong, X.-Z. Wang, Z. He, A.B. Djurisic, C.-T. Yip, K.-Y. Cheung, H. Wang, C.S.K. Mak, W.-K. Chan, Nature Mater. 6, 521–527 (2007)

    Article  CAS  Google Scholar 

  50. W.-Y. Wong, G.-J. Zhou, Z. He, K.-Y. Cheung, A.M.-C. Ng, A.B. Djurisic, W.-K. Chan, Macromol. Chem. Phys. 209, 1319–1332 (2008)

    Article  CAS  Google Scholar 

  51. A. Koehler, A.L.T. Khan, J.S. Wilson, C. Dosche, M.K. Al-Suti, H.H. Shah, M.S. Khan, J. Chem. Phys. 136, 094905–094913 (2012)

    Article  Google Scholar 

  52. M.-H. Nguyen, V.H. Nguyen, J.H.K. Yip, Organometallics 32, 7283–7291 (2013)

    Article  CAS  Google Scholar 

  53. M.-H. Nguyen, J.H.K. Yip, Organometallics 31, 7522–7531 (2012)

    Article  CAS  Google Scholar 

  54. M.-H. Nguyen, J.H.K. Yip, Organometallics 30, 6383–6392 (2011)

    Article  CAS  Google Scholar 

  55. 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)

    Article  CAS  Google Scholar 

  56. H. Jia, B. Kucukoz, Y. Xing, P. Majumdar, C. Zhang, A. Karatay, H.G. Yaglioglu, A. Elmali, J. Zhao, M. Hayvali, J. Mater. Chem. C 2, 9720–9736 (2014)

    Article  CAS  Google Scholar 

  57. S. Zhang, Y. Sheng, G. Wei, Y. Quan, Y. Cheng, C. Zhu, J. Polym. Sci. Pol. Chem. 52, 1686–1692 (2014)

    Article  CAS  Google Scholar 

  58. W. Wu, J. Zhao, H. Guo, J. Sun, S. Ji, Z. Wang, Chem. Euro. J. 18, 1961–1968 (2012)

    Article  CAS  Google Scholar 

  59. W. Wu, J. Zhao, J. Sun, L. Huang, X. Yi, J. Mater. Chem. C 1, 705–716 (2013)

    Article  CAS  Google Scholar 

  60. M.J. Frisch et al., Gaussian, Inc., Wallingford CT (2004)

  61. P. Hohenberg, W. Kohn, J. Phys. Rev. 136, 864–871 (1964)

    Article  Google Scholar 

  62. P. Hohenberg, W. Kohn, J. Phys. Rev. 140, 1133–1138 (1965)

    Article  Google Scholar 

  63. R.G. Parr, W. Yang, Density-functional theory of atoms and molecules (Oxford University Press, Oxford, 1989)

    Google Scholar 

  64. D.R. Salahub, M.C. Zerner, The challenge of d and f electrons (American Chemical Society, Washington, DC, 1989)

    Book  Google Scholar 

  65. R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 256, 454–464 (1996)

    Article  CAS  Google Scholar 

  66. M.E. Casida, C. Jamorski, K.C. Casida, D.R. Salahub, J. Chem. Phys. 108, 4439–4449 (1998)

    Article  CAS  Google Scholar 

  67. R.E. Stratmann, G.E. Scuseria, M.J. Frisch, J. Chem. Phys. 109, 8218–8224 (1998)

    Article  CAS  Google Scholar 

  68. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785–789 (1988)

    Article  CAS  Google Scholar 

  69. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 157, 200–206 (1989)

    Article  CAS  Google Scholar 

  70. A.D. Becke, J. Chem. Phys. 98, 5648–5652 (1993)

    Article  CAS  Google Scholar 

  71. N.M. O’Boyle, A.L. Tenderholt, K.M. Langner, J. Comput. Chem. 29, 839–845 (2008)

    Article  Google Scholar 

  72. J.S. Binkley, J.A. Pople, W.J. Hehre, J. Am. Chem. Soc. 102, 939–947 (1980)

    Article  CAS  Google Scholar 

  73. M.S. Gordon, J.S. Binkley, J.A. Pople, W.J. Pietro, W.J. Hehre, J. Am. Chem. Soc. 104, 2797–2803 (1982)

    Article  CAS  Google Scholar 

  74. W.J. Pietro, M.M. Francl, W.J. Hehre, D.J. Defrees, J.A. Pople, J.S. Binkley, J. Am. Chem. Soc. 104, 5039–5048 (1982)

    Article  CAS  Google Scholar 

  75. K.D. Dobbs, W.J. Hehre, J. Comput. Chem. 7, 359–378 (1986)

    Article  CAS  Google Scholar 

  76. K.D. Dobbs, W.J. Hehre, J. Comput. Chem. 8, 861–879 (1987)

    Article  CAS  Google Scholar 

  77. K.D. Dobbs, W.J. Hehre, J. Comput. Chem. 8, 880–893 (1987)

    Article  CAS  Google Scholar 

  78. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 105, 2999–3093 (2005)

    Article  CAS  Google Scholar 

  79. D. Osella, R. Gobetto, C. Nervi, M. Ravera, R. D’Amato, M.V. Russo, Inorg. Chem. Commun. 1, 239–245 (1998)

    Article  CAS  Google Scholar 

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Acknowledgments

This research was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), le Fonds Québécois de la Recherche sur la Nature et les Technologies (FQRNT), the Centre d’Études des Matériaux Optiques et Photoniques de l’Université de Sherbrooke (CEMOPUS), and the Agence National de la Recherche (ANR) for a grant of a Research Chair of Excellence.

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    Antoine Bonnot & Pierre D. Harvey

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This paper is dedicated of Professor Anatoli D. Pomogailo.

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Bonnot, A., Harvey, P.D. Pentacene- and BODIPY-Containing trans-Bis(ethynyl)bis(phosphine)platinum(II) Organometallic Polymers: A DFT Point of View. J Inorg Organomet Polym 26, 1328–1337 (2016). https://doi.org/10.1007/s10904-016-0405-8

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