Skip to main content
Log in

Narrow Bandgap Platinum(II)-Containing Polyynes with Diketopyrrolopyrrole and Isoindigo Spacers

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

Two new solution-processible platinum(II) polyyne polymers P1 and P2 bridged by diketopyrrolopyrrole and isoindigo units have been synthesized via the CuI-catalyzed dehydrohalogenation reaction of the platinum(II) chloride precursors and the corresponding diacetylene ligands. The photophysical and electrochemical properties of P1 and P2 were investigated. These metallo-organic polymers have relatively narrow bandgaps of around 1.58–1.70 eV and broad absorption bands which are favorable for harvesting solar energy.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. E.G. Wang, L.T. Hou, Z.Q. Wang, S. Hellström, F.L. Zhang, O. Inganäs, M.R. Andersson, Adv. Mater. 22, 5240 (2010)

    Article  CAS  Google Scholar 

  2. E.G. Wang, Z.F. Ma, Z. Zhang, P. Henriksson, O. Inganäs, F.L. Zhang, M.R. Andersson, Chem. Commun. 47, 4908 (2011)

    Article  CAS  Google Scholar 

  3. D.H. Wang, A.K.K. Kyaw, J.-R. Pouliot, M. Leclerc, A.J. Heeger, Adv. Energy Mater. 4, 1300835 (2014)

    Google Scholar 

  4. P.T. Boudreault, A. Najari, M. Leclerc, Chem. Mater. 23, 456 (2011)

    Article  CAS  Google Scholar 

  5. J. Peet, M.L. Senatore, A.J. Heeger, G.C. Bazan, Adv. Mater. 21, 1521 (2009)

    Article  CAS  Google Scholar 

  6. Y. Lin, Y. Li, X. Zhan, Chem. Soc. Rev. 41, 4245 (2012)

    Article  CAS  Google Scholar 

  7. F. Silvestri, M.D. Irwin, L. Beverina, A. Facchetti, G.A. Pagani, T.J. Marks, J. Am. Chem. Soc. 130, 17640 (2008)

    Article  CAS  Google Scholar 

  8. J.W. Arbogast, C.S. Foote, J. Am. Chem. Soc. 113, 8886 (1991)

    Article  CAS  Google Scholar 

  9. G.J. Zhao, Y.J. He, Y.F. Li, Adv. Mater. 22, 4355 (2010)

    Article  CAS  Google Scholar 

  10. S. Günes, H. Neugebauer, N.S. Sariciftci, Chem. Rev. 107, 1324 (2007)

    Article  Google Scholar 

  11. P. Cheng, X.G. Zhao, W.Y. Zhou, J.H. Hou, Y.F. Li, X.W. Zhan, Org. Electron. 15, 2270 (2014)

    Article  CAS  Google Scholar 

  12. Z. He, C. Zhong, S. Su, M. Xu, H. Wu, Y. Cao, Nat. Photonics 6, 591 (2012)

    Google Scholar 

  13. B. Walker, C. Kim, T.-Q. Nguyen, Chem. Mater. 23, 470 (2011)

    Article  CAS  Google Scholar 

  14. D.H. Wang, A.K.K. Kyaw, V. Gupta, G.C. Bazan, A.J. Heeger, Adv. Energy Mater. 3, 1161 (2013)

    Article  CAS  Google Scholar 

  15. A.K.K. Kyaw, D.H. Wang, D. Wynands, J. Zhang, T.-Q. Nguyen, G.C. Bazan, A.J. Heeger, Nano Lett. 13, 3796 (2013)

    Article  CAS  Google Scholar 

  16. Q. Liu, H.M. Zhan, C.-L. Ho, F.-R. Dai, Y.Y. Fu, Z.Y. Xie, L.X. Wang, J.-H. Li, F. Yan, S.P. Huang, W.-Y. Wong, Chem. Asian J. 8, 1892 (2013)

    Article  CAS  Google Scholar 

  17. G. Yu, J. Gao, J.C. Hummelen, F.A. Wudl, A.J. Heeger, Science 270, 1789 (1995)

    Article  CAS  Google Scholar 

  18. W. Ma, C. Yang, X. Gong, K. Lee, A.J. Heeger, Adv. Funct. Mater. 15, 1617 (2005)

    Article  CAS  Google Scholar 

  19. Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Chem. Rev. 109, 5868 (2009)

    Article  CAS  Google Scholar 

  20. W.-Y. Wong, X.-Z. Wang, Z. He, A.B. Djurišić, C.-T. Yip, K.-Y. Cheung, H. Wang, C.S.-K. Mak, W.-K. Chan, Nat. Mater. 6, 521 (2007)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  22. C. Qin, Y. Fu, C.-H. Chui, C.-W. Kan, Z. Xie, L. Wang, W.-Y. Wong, Macromol. Rapid Commun. 32, 1472 (2011)

    Article  CAS  Google Scholar 

  23. H.M. Zhan, S. Lamare, A. Ng, T. Kenny, H. Guernon, W.-K. Chan, A.B. Djurišić, P.D. Harvey, W.-Y. Wong, Macromolecules 44, 5155 (2011)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  25. J. Lee, S.B. Jo, M. Kim, H.G. Kim, J. Shin, H. Kim, K. Cho, Adv. Mater. (2014). doi:10.1002/adma.201401203

    Google Scholar 

  26. M.M. Wienk, M. Turbiez, J. Gilot, R.A.J. Janssen, Adv. Mater. 20, 2556 (2008)

    Article  CAS  Google Scholar 

  27. E.J. Zhou, S. Yamakawa, K. Tajima, C.H. Yang, K. Hashimoto, Chem. Mater. 21, 4055 (2009)

    Article  CAS  Google Scholar 

  28. W.W. Li, W.S.C. Roelofs, M. Turbiez, M.M. Wienk, R.A.J. Janssen, Adv. Mater. 26, 3304 (2014)

    Article  CAS  Google Scholar 

  29. W.W. Li, A. Furlan, W.S.C. Roelofs, K.H. Hendriks, G.W.P.V. Pruissen, M.M. Wienk, R.A.J. Janssen, Chem. Commun. 50, 679 (2014)

    Article  CAS  Google Scholar 

  30. E.G. Wang, Z.F. Ma, Z. Zhang, P. Henriksson, O. Inganäs, F.L. Zhang, M.R. Andersson, Chem. Commun. 47, 4908 (2011)

    Article  CAS  Google Scholar 

  31. J.G. Mei, K.R. Graham, R. Stalder, J.R. Reynolds, Org. Lett. 12, 660 (2010)

    Article  CAS  Google Scholar 

  32. G.B. Zhang, Y.Y. Fu, Z.Y. Xie, Q. Zhang, Macromolecules 44, 1414 (2011)

    Article  CAS  Google Scholar 

  33. A.B. Tamayo, M. Tantiwiwat, B. Walker, T.-Q. Nguyen, J. Phys. Chem. C 112, 15543 (2008)

    Article  CAS  Google Scholar 

  34. T. Lei, Y. Cao, Y.L. Fan, C.-J. Liu, S.-C. Yuan, J. Pei, J. Am. Chem. Soc. 133, 6099 (2011)

    Article  CAS  Google Scholar 

  35. J. Chatt, R. G. Hayter, J. Chem. Soc. Dalton Trans. 896 (1961)

  36. W.-Y. Wong, W.-K. Wong, P. R. Raithby, J. Chem. Soc. Dalton Trans. 2761 (1998)

  37. W.-Y. Wong, S.-M. Chan, K.-H. Choi, K.-W. Cheah, W.-K. Chan, Macromol. Rapid Commun. 21, 453 (2000)

    Article  CAS  Google Scholar 

  38. J.W. Jung, F. Liu, T.P. Russell, W.H. Jo, Chem. Commun. 49, 8495 (2013)

    Article  CAS  Google Scholar 

  39. E.G. Wang, W. Mammo, M.R. Andersson, Adv. Mater. 26, 1801 (2014)

    Article  CAS  Google Scholar 

  40. N. Chawdhury, A. Köhler, R.H. Friend, W.Y. Wong, J. Lewis, M. Younus, P.R. Raithby, T.C. Corcoran, M.R.A. Al-Mandhary, M.S. Khan, J. Chem. Phys. 110, 4963 (1999)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  43. W.-Y. Wong, S.-Y. Poon, J.-X. Shi, K.-W. Cheah, J. Polym. Sci., Part A: Polym. Chem. 44, 4804 (2006)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  45. Q.J. Sun, H.Q. Wang, C.H. Yang, Y.F. Li, J. Mater. Chem. 13, 800 (2003)

    Article  CAS  Google Scholar 

  46. Y.F. Li, Y. Cao, J. Gao, D.L. Wang, G. Yu, A.J. Heeger, Synth. Met. 99, 243 (1999)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  48. P.M. Beaujuge, H.N. Tsao, M.R. Hansen, C.M. Amb, J.R. Reynolds, J. Am. Chem. Soc. 134, 8944 (2012)

    Article  CAS  Google Scholar 

  49. Y.J. He, G.J. Zhao, B. Peng, Y.F. Li, Adv. Funct. Mater. 20, 3383 (2010)

    Article  CAS  Google Scholar 

  50. H.Y. Chen, J.H. Hou, S.Q. Zhang, Y.Y. Liang, G.W. Yang, Y. Yang, L.P. Yu, Y. Wu, G. Li, Nat. Photonics 3, 649 (2009)

    Article  CAS  Google Scholar 

  51. L.J.A. Koster, V.D. Mihailetchi, R. Ramaker, P.W.M. Blom, Appl. Phys. Lett. 86, 123509–123511 (2005)

    Article  Google Scholar 

  52. C.J. Brabec, A. Cravino, D. Meissner, N.S. Sariciftci, T. Fromherz, M.T. Rispens, L. Sanchez, J.C. Hummelen, Adv. Funct. Mater. 11, 374 (2001)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the National Natural Science Foundation of China (Project Number 51373145), Hong Kong Baptist University (FRG2/12-13/083), Hong Kong Research Grants Council (HKBU203312 and HKUST2/CRF/10) and Areas of Excellence Scheme, University Grants Committee of HKSAR (project No. AoE/P-03/08) for financial support. The work was also supported by Partner State Key Laboratory of Environmental and Biological Analysis (SKLP-14-15-P011) and Strategic Development Fund of HKBU. The project was also supported by Open Research Fund of State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences. Y. H. Lo gratefully acknowledges the financial support from the National Science Council of Taiwan (NSC 102-2113-M-845-001) and the project of the specific research fields in the University of Taipei, Taiwan. H. Li thanks the 111 Project and Beijing Engineering Research Center of Food Environment and Public Health from Minzu University of China (Nos. B08044 and 10301-01404026) for financial support.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Cheuk-Lam Ho, Yih Hsing Lo or Wai-Yeung Wong.

Additional information

Dedicated to Prof. Benzhong Tang in honor of his outstanding contributions to the field of Inorganic and Organometallic Polymers.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, Q., Ho, CL., Lo, Y.H. et al. Narrow Bandgap Platinum(II)-Containing Polyynes with Diketopyrrolopyrrole and Isoindigo Spacers. J Inorg Organomet Polym 25, 159–168 (2015). https://doi.org/10.1007/s10904-014-0120-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-014-0120-2

Keywords

Navigation