New AIE-Active Copolymers with Au(I) Isocyanide Acrylate Units

Abstract

The development of new organometallic materials with aggregation-induced emission (AIE) characteristics is pursuing due to their wide prospects in various application fields. In this work, we synthesized Au(I)-containing copolymers (P13) by copolymerization of methyl methacrylate (MMA) monomers, carrying Au(I) isocyanide acrylate unit and MMA in different molar ratios. All polymers exhibited AIE activities due to the introduction of the Au(I) isocyanide units. Increasing the Au(I) content in the polymers could effectively facilitate their emission. In addition, polymer P3 was demonstrated as a sensitive fluorescent probe for explosive detection.

This is a preview of subscription content, access via your institution.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

References

  1. 1.

    C.-T. Chen, Chem. Mater. 16, 4389–4400 (2004)

    CAS  Google Scholar 

  2. 2.

    R. Friend, R. Gymer, A. Holmes, J. Burroughes, R. Marks, C. Taliani, D. Bradley, D. Dos Santos, J. Bredas, M. Lögdlund, Nature 397, 121 (1999)

    CAS  Google Scholar 

  3. 3.

    J. Luo, Z. Xie, J.W.Y. Lam, L. Cheng, H. Chen, C. Qiu, H.S. Kwok, X. Zhan, Y. Liu, D. Zhu, B.Z. Tang, Chem. Commun. 18, 1740–1741 (2001)

    Google Scholar 

  4. 4.

    J. Mei, Y. Hong, J.W.Y. Lam, A. Qin, Y. Tang, B.Z. Tang, Adv. Mater. 26, 5429–5479 (2014)

    CAS  PubMed  Google Scholar 

  5. 5.

    B. Chen, B. Liu, J. Zeng, H. Nie, Y. Xiong, J. Zou, H. Ning, Z. Wang, Z. Zhao, B.Z. Tang, Adv. Funct. Mater. 28, 1803369 (2018)

    Google Scholar 

  6. 6.

    H. Liu, J. Zeng, J. Guo, H. Nie, Z. Zhao, B.Z. Tang, Angew. Chem. Int. Ed. 57, 9290–9294 (2018)

    CAS  Google Scholar 

  7. 7.

    S.-C. Lo, P.L. Burn, Chem. Rev. 107, 1097–1116 (2007)

    CAS  PubMed  Google Scholar 

  8. 8.

    A. Moliton, R.C. Hiorns, Polym. Int. 53, 1397–1412 (2004)

    CAS  Google Scholar 

  9. 9.

    X. Feng, L. Liu, S. Wang, D. Zhu, Chem. Soc. Rev. 39, 2411–2419 (2010)

    CAS  PubMed  Google Scholar 

  10. 10.

    A. Qin, J.W.Y. Lam, B.Z. Tang, Prog. Polym. Sci. 37, 182–209 (2012)

    CAS  Google Scholar 

  11. 11.

    A. Qin, J.W.Y. Lam, L. Tang, C.K.W. Jim, H. Zhao, J. Sun, B.Z. Tang, Macromolecules 42, 1421–1424 (2009)

    CAS  Google Scholar 

  12. 12.

    T. Han, H. Deng, Z. Qiu, Z. Zhao, H. Zhang, H. Zou, N.L.C. Leung, G. Shan, M.R.J. Elsegood, J.W.Y. Lam, B.Z. Tang, J. Am. Chem. Soc. 140, 5588–5598 (2018)

    CAS  PubMed  Google Scholar 

  13. 13.

    B. He, H. Su, T. Bai, Y. Wu, S. Li, M. Gao, R. Hu, Z. Zhao, A. Qin, J. Ling, B.Z. Tang, J. Am. Chem. Soc. 139, 5437–5443 (2017)

    CAS  PubMed  Google Scholar 

  14. 14.

    B. He, Y. Wu, A. Qin, B.Z. Tang, Macromolecules 50, 5719–5728 (2017)

    CAS  Google Scholar 

  15. 15.

    R.-H. Chien, C.-T. Lai, J.-L. Hong, J. Phys. Chem. C 115, 12358–12366 (2011)

    CAS  Google Scholar 

  16. 16.

    A. Pucci, R. Rausa, F. Ciardelli, Macromol. Chem. Phys. 209, 900–906 (2008)

    CAS  Google Scholar 

  17. 17.

    M.A. Rawashdeh-Omary, J.M. López-de-Luzuriaga, M.D. Rashdan, O. Elbjeirami, M. Monge, M. Rodríguez-Castillo, A. Laguna, J. Am. Chem. Soc. 131, 3824–3825 (2009)

    CAS  PubMed  Google Scholar 

  18. 18.

    P. Nguyen, P. Gómez-Elipe, I. Manners, Chem. Rev. 99, 1515–1548 (1999)

    CAS  PubMed  Google Scholar 

  19. 19.

    C.E. Carraher, M.R. Roner, K. Shahi, A. Moric-Johnson, L. Miller, G. Barot, A. Battin, N.T. Trang, M.H. Al-Huniti, J. Inorg. Organomet. Polym. Mater. 25, 386–399 (2015)

    CAS  Google Scholar 

  20. 20.

    X. Zhai, H. Yu, L. Wang, Z. Deng, Z.U. Abdin, R. Tong, X. Yang, Y. Chen, M. Saleem, Appl. Organomet. Chem. 30, 62–72 (2016)

    CAS  Google Scholar 

  21. 21.

    A.S. Abd-El-Aziz, Macromol. Rapid Commun. 23, 995–1031 (2002)

    CAS  Google Scholar 

  22. 22.

    K.A. Williams, A.J. Boydston, C.W. Bielawski, Chem. Soc. Rev. 36, 729–744 (2007)

    CAS  PubMed  Google Scholar 

  23. 23.

    X. Feng, X. Sui, M.A. Hempenius, G.J. Vancso, J. Am. Chem. Soc. 136, 7865–7868 (2014)

    CAS  PubMed  Google Scholar 

  24. 24.

    W.-Y. Wong, Coord. Chem. Rev. 251, 2400–2427 (2007)

    CAS  Google Scholar 

  25. 25.

    K. Omri, N. Alonizan, J. Inorg. Organomet. Polym. Mater. 29, 203–212 (2019)

    CAS  Google Scholar 

  26. 26.

    K. Omri, A. Alyamani, L. El Mir, Appl. Phys. A 124, 215 (2018)

    CAS  Google Scholar 

  27. 27.

    M.N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 510, 485 (2014)

    CAS  PubMed  Google Scholar 

  28. 28.

    J. Lima, L. Rodríguez, Inorganics 3, 1 (2015)

    CAS  Google Scholar 

  29. 29.

    C. Jobbágy, A. Deák, Eur. J. Inorg. Chem. 2014, 4434–4449 (2014)

    Google Scholar 

  30. 30.

    T. Zou, C.-N. Lok, P.-K. Wan, Z.-F. Zhang, S.-K. Fung, C.-M. Che, Curr. Opin. Chem. Biol. 43, 30–36 (2018)

    CAS  PubMed  Google Scholar 

  31. 31.

    E.R.T. Tiekink, Coord. Chem. Rev. 275, 130–153 (2014)

    CAS  Google Scholar 

  32. 32.

    A. Pinto, N. Svahn, J.C. Lima, L. Rodríguez, Dalton Trans. 46, 11125–11139 (2017)

    CAS  PubMed  Google Scholar 

  33. 33.

    Z. Luo, X. Yuan, Y. Yu, Q. Zhang, D.T. Leong, J.Y. Lee, J. Xie, J. Am. Chem. Soc. 134, 16662–16670 (2012)

    CAS  PubMed  Google Scholar 

  34. 34.

    Z. Chen, Z. Li, F. Hu, G.-A. Yu, J. Yin, S.H. Liu, Dyes Pigments 125, 169–178 (2016)

    CAS  Google Scholar 

  35. 35.

    W.-X. Ni, M. Li, J. Zheng, S.-Z. Zhan, Y.-M. Qiu, S.W. Ng, D. Li, Angew. Chem. Int. Ed. 52, 13472–13476 (2013)

    CAS  Google Scholar 

  36. 36.

    Z. Chen, J. Zhang, M. Song, J. Yin, G.-A. Yu, S.H. Liu, Chem. Commun. 51, 326–329 (2015)

    CAS  Google Scholar 

  37. 37.

    J. Zhang, Q. Liu, W. Wu, J. Peng, H. Zhang, F. Song, B. He, X. Wang, H.H.Y. Sung, M. Chen, B.S. Li, S.H. Liu, J.W.Y. Lam, B.Z. Tang, ACS Nano 13, 3618–3628 (2019)

    CAS  PubMed  Google Scholar 

  38. 38.

    E. Aguiló, A.J. Moro, R. Gavara, I. Alfonso, Y. Pérez, F. Zaccaria, C.F. Guerra, M. Malfois, C. Baucells, M. Ferrer, J.C. Lima, L. Rodríguez, Inorg. Chem. 57, 1017–1028 (2018)

    PubMed  Google Scholar 

  39. 39.

    J. Liang, Z. Chen, J. Yin, G.-A. Yu, S.H. Liu, Chem. Commun. 49, 3567–3569 (2013)

    CAS  Google Scholar 

  40. 40.

    J. Liang, Z. Chen, L. Xu, J. Wang, J. Yin, G.-A. Yu, Z.-N. Chen, S.H. Liu, J. Mater. Chem. C 2, 2243–2250 (2014)

    CAS  Google Scholar 

  41. 41.

    Z. Chen, D. Wu, X. Han, J. Liang, J. Yin, G.-A. Yu, S.H. Liu, Chem. Commun. 50, 11033–11035 (2014)

    CAS  Google Scholar 

  42. 42.

    L. Zhang, Z. Liu, X. Zhang, J. Chen, Y. Cao, J. Inorg. Organomet. Polym. Mater. 25, 64–72 (2015)

    CAS  Google Scholar 

  43. 43.

    L. Shi, L. Zhu, J. Guo, L. Zhang, Y. Shi, Y. Zhang, K. Hou, Y. Zheng, Y. Zhu, J. Lv, S. Liu, Z. Tang, Angew. Chem. Int. Ed. 56, 15397–15401 (2017)

    CAS  Google Scholar 

  44. 44.

    Y. Salinas, R. Martínez-Máñez, M.D. Marcos, F. Sancenón, A.M. Costero, M. Parra, S. Gil, Chem. Soc. Rev. 41, 1261–1296 (2012)

    CAS  PubMed  Google Scholar 

  45. 45.

    J. Wang, J. Mei, W. Yuan, P. Lu, A. Qin, J. Sun, Y. Ma, B.Z. Tang, J. Mater. Chem. 21, 4056–4059 (2011)

    CAS  Google Scholar 

Download references

Acknowledgements

We are grateful for financial support from the National Natural Science Foundation of China (21788102, 21490570, 21490574 and 21472059), the Research Grants Council of Hong Kong (16305618, C6009-17G, and A-HKUST605/16), the Innovation and Technology Commission (ITC-CNERC14SC01), and the Science and Technology Plan of Shenzhen (JCYJ20160229205601482 and JCYJ20170818113602462).

Author information

Affiliations

Authors

Corresponding authors

Correspondence to Sheng Hua Liu or Jacky W. Y. Lam or Ben Zhong Tang.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 11282 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Zhang, J., Zou, H., Wang, X. et al. New AIE-Active Copolymers with Au(I) Isocyanide Acrylate Units. J Inorg Organomet Polym 30, 1490–1496 (2020). https://doi.org/10.1007/s10904-019-01279-w

Download citation

Keywords

  • Aggregation-induced emission
  • Au(I) isocyanide
  • Fluorescent sensor
  • Explosive detection