Skip to main content
Log in

Luminescent mesoporous hybrid materials grafted with lanthanide complexes synthesized by Michael-like addition reaction

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

New kind of luminescent mesoporous hybrid materials were prepared via Michael-like addition reaction. 4-Vinylpyridine-2,6-dicarboxylic acid was selected as a bifunctional chelating ligand, which contains (1) an electron deficient double bond that can react with the thiol group of mesoporous silica by Michael-like addition reaction, (2) a metal chelating unit. The luminescent hybrid materials [MCM-41-SH-Ln(DPA)3, Ln = Tb, Eu] can be prepared through Michael-like addition reaction of thiol-functional MCM-41 and 4-vinylpyridine-2,6-dicarboxylic acid, and then assembling with lanthanide ions and pyridine-2,6-dicarboxylic acid (DPA). FT-IR, XRD, UV–Vis, TEM, N2 adsorption/desorption and photoluminescence measurements were employed to characterize the mesostructure, composition and optical properties of these hybrids. The results reveal that the lanthanide complexes were successfully grafted onto the functional MCM-41, and the ordered mesoporous structure of MCM-41 were preserved after the grafting procedure. Under the excitation of UV light, the obtained MCM-41-SH-Tb(DPA)3 and MCM-41-SH-Eu(DPA)3 exhibit bright green and red emission, long luminescent lifetimes and high quantum efficiency.

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
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. H. Zhu, J.L. Fan, B.H. Wang, X.J. Peng, Chem. Soc. Rev. 44, 4337–4366 (2015)

    Article  CAS  PubMed  Google Scholar 

  2. C. Perego, R. Millini, Chem. Soc. Rev. 42, 3956–3976 (2013)

    Article  CAS  PubMed  Google Scholar 

  3. P.P. Yang, S.L. Gai, J. Lin, Chem. Soc. Rev. 41, 3679–3698 (2012)

    Article  CAS  PubMed  Google Scholar 

  4. J. Feng, H.J. Zhang, Chem. Soc. Rev. 42, 387–410 (2013)

    Article  CAS  PubMed  Google Scholar 

  5. B. Yan, RSC Adv. 2, 9304–9324 (2012)

    Article  CAS  Google Scholar 

  6. K. Binnemans, Chem. Rev. 109, 4283–4373 (2009)

    Article  CAS  PubMed  Google Scholar 

  7. D.B. Ambili Raj, S. Biju, M.L.P. Reddy, J. Mater. Chem. 19, 7976–7983 (2009)

    Article  CAS  Google Scholar 

  8. V. Divya, S. Biju, R.L. Varma, M.L.P. Reddy, J. Mater. Chem. 20, 5220–5227 (2010)

    Article  CAS  Google Scholar 

  9. Z. Zhou, Y.H. Zheng, Q.M. Wang, Inorg. Chem. 53, 1530–1536 (2014)

    Article  CAS  PubMed  Google Scholar 

  10. Y. Liu, L.N. Sun, J.L. Liu, Y.X. Peng, X.Q. Ge, L.Y. Shi, W. Huang, Dalton Trans. 44, 237–246 (2015)

    Article  CAS  PubMed  Google Scholar 

  11. M. Ilibi, T.B. de Queiroz, J.J. Ren, L. De Cola, A.S.S. de Camargo, H. Eckert, Dalton Trans. 43, 8318–8330 (2014)

    Article  CAS  PubMed  Google Scholar 

  12. L. Chen, B. Yan, Dalton Trans. 43, 14123–14131 (2014)

    Article  CAS  PubMed  Google Scholar 

  13. D.J. Zhang, X.M. Wang, Z.A. Qiao, D.H. Tang, Y.L. Liu, Q.S. Huo, J. Phys. Chem. C 114, 12505–12510 (2010)

    Article  CAS  Google Scholar 

  14. L.D. Carlos, R.A.S. Ferreira, V. de Zea Bermudez, S.J.L. Ribeiro, Adv. Mater. 21, 509–534 (2009)

    Article  CAS  PubMed  Google Scholar 

  15. D.C. Oliveira, A.G. Macedo, N.J.O. Silva, C. Molina, R.A.S. Ferreira, P.S. André, K. Dahmouche, V. de Zea Bermudez, Y. Messaddeq, S.J.L. Ribeiro, L.D. Carlos, Chem. Mater. 20, 3696–3705 (2008)

    Article  CAS  Google Scholar 

  16. E.P. Legaria, I. Saldan, P. Svedlindh, E. Wetterskog, K. Gunnarsson, V.G. Kessler, G.A. Seisenbaeva, Dalton Trans. 47, 1312–1320 (2018)

    Article  Google Scholar 

  17. B.D. Mather, K. Viswanathan, K.M. Miller, T.E. Long, Prog. Polym. Sci. 31, 487–531 (2006)

    Article  CAS  Google Scholar 

  18. S. Kumari, B. Malvi, A.K. Ganai, V.K. Pillai, S.S. Gupta, J. Phys. Chem. C 115, 17774–17781 (2011)

    Article  CAS  Google Scholar 

  19. A.L. Gassner, C. Duhot, J.C.G. Bünzli, A.S. Chauvin, Inorg. Chem. 47, 7802–7812 (2008)

    Article  CAS  PubMed  Google Scholar 

  20. J.B. Lamture, Z.H. Zhou, A.S. Kumar, T.G. Wensel, Inorg. Chem. 34, 864–869 (1995)

    Article  CAS  Google Scholar 

  21. J.H. Zhao, S. Wang, S.S. Lu, J. Sun, X.R. Yang, Nanoscale 10, 7163–7170 (2018)

    Article  CAS  PubMed  Google Scholar 

  22. Q.F. Li, D. Yue, G.W. Ge, X.D. Du, Y.C. Gong, Z.L. Wang, J.H. Hao, Dalton Trans. 44, 16810–16817 (2015)

    Article  CAS  PubMed  Google Scholar 

  23. Q.F. Li, X.D. Du, L. Jin, M.M. Hou, Z.L. Wang, J.H. Hao, J. Mater. Chem. C 4, 3195–3201 (2016)

    Article  CAS  Google Scholar 

  24. A.M. Raitsimring, C. Gunanathan, A. Potapov, I. Efremenko, J.M.L. Martin, D. Milstein, D. Goldfarb, J. Am. Chem. Soc. 129, 14138–14139 (2007)

    Article  CAS  PubMed  Google Scholar 

  25. S.E. Denmark, C.R. Butler, Org. Lett. 8, 63–66 (2006)

    Article  CAS  PubMed  Google Scholar 

  26. C.M. Crudden, M. Sateesh, R. Lewis, J. Am. Chem. Soc. 127, 10045–10050 (2005)

    Article  CAS  PubMed  Google Scholar 

  27. F.H. Ma, J.L. Chen, Q.F. Li, H.H. Zuo, F. Huang, X.C. Su, Chem. Asian. J. 9, 1808–1816 (2014)

    Article  CAS  PubMed  Google Scholar 

  28. F. Wei, Q. Hou, J.Y. Yang, J.H. Zhu, J. Colloid Interface Sci. 356, 526–535 (2011)

    Article  CAS  PubMed  Google Scholar 

  29. D. Margolese, J.A. Melero, S.C. Christiansen, B.F. Chmelka, G.D. Stucky, Chem. Mater. 12, 2448–2459 (2000)

    Article  CAS  Google Scholar 

  30. K. Dhara, K. Sarkar, D. Srimani, S.K. Saha, P. Chattopadhyay, A. Bhaumik, Dalton Trans. 39, 6395–6402 (2010)

    Article  CAS  PubMed  Google Scholar 

  31. Q.F. Li, D. Yue, W. Lu, X.L. Zhang, C.Y. Li, Z.L. Wang, Sci. Rep. 5, 8385 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. M.R. Felício, T.G. Nunes, P.M. Vaz, A.M.P. Botas, P. Ribeiro-Claro, R.A.S. Ferreira, R.O. Freire, P.D. Vaz, L.D. Carlos, C.D. Nunes, M.M. Nolasco, J. Mater. Chem. C 2, 9701–9711 (2014)

    Article  CAS  Google Scholar 

  33. M.H. Lim, A. Stein, Chem. Mater. 11, 3285–3295 (1999)

    Article  CAS  Google Scholar 

  34. H. Chen, Y.J. Xie, A.M. Kirillov, L.L. Liu, M.H. Yu, W.S. Liu, Y. Tang, Chem. Commun. 51, 5036–5039 (2015)

    Article  CAS  Google Scholar 

  35. C.J. Gao, A.M. Kirillov, W. Dou, X.L. Tang, L.L. Liu, X.H. Yan, Y.J. Xie, P.X. Zang, W.S. Liu, Y. Tang, Inorg. Chem. 53, 935–942 (2014)

    Article  CAS  PubMed  Google Scholar 

  36. A.R. Ramya, D. Sharma, S. Natarajan, M.L.P. Reddy, Inorg. Chem. 51, 8818–8826 (2012)

    Article  CAS  PubMed  Google Scholar 

  37. Z.S. Dou, J.C. Yu, Y.J. Cui, Y. Yang, Z.Y. Wang, D. Yang, G.D. Qian, J. Am. Chem. Soc. 136, 5527–5530 (2014)

    Article  CAS  PubMed  Google Scholar 

  38. Z.Z. Zhang, L. Wang, G.P. Li, B.X. Ye, Analyst 142, 1821–1826 (2017)

    Article  CAS  PubMed  Google Scholar 

  39. G. Jones, V. Vullev, Photochem. Photobiol. Sci. 1, 925–933 (2002)

    Article  CAS  PubMed  Google Scholar 

  40. Y.R. Shi, G.W. Ge, L.X. Yang, C.Y. Li, Z.L. Wang, J. Mater. Sci. Mater. Electron. 29, 771–777 (2018)

    Article  CAS  Google Scholar 

  41. T.R. Wang, P. Li, H.R. Li, ACS App. Mater. Inter. 6, 12915–12921 (2014)

    Article  CAS  Google Scholar 

  42. S. Ogate, N. Goto, S. Sakurai, A. Ishii, M. Hatanaka, K. Yoshihara, R. Tanabe, K. Kayano, R. Magaribuchi, K. Goto, M. Hasegawa, Dalton Trans. 47, 7135–7143 (2018)

    Article  Google Scholar 

  43. Y. Kitagawa, F. Suzue, T. Nakanishi, K. Fushimi, Y. Hasegawa, Dalton Trans. 47, 7327–7332 (2018)

    Article  CAS  PubMed  Google Scholar 

  44. T.T. Wen, H.R. Li, Y.G. Wang, L.Y. Wang, W.J. Zhang, L. Zhang, J. Mater. Chem. C 1, 1607–1612 (2013)

    Article  CAS  Google Scholar 

  45. Y.J. Li, D.Y. Xie, X.L. Pang, X.D. Yu, T. Yu, X.T. Ge, Sens. Actuators B 227, 660–667 (2016)

    Article  CAS  Google Scholar 

  46. Y.H. Zhang, B. Li, H.P. Ma, L.M. Zhang, W.X. Zhang, J. Mater. Chem. C 5, 4661–4669 (2017)

    Article  CAS  Google Scholar 

  47. R.S. Ningthoujam, A. Sharma, K.S. Sharma, K.C. Barick, P.A. Hassan, R.K. Vatsa, RSC Adv. 5, 68234–68242 (2015)

    Article  CAS  Google Scholar 

  48. A.I. Prasad, A.K. Parchur, R.R. Juluri, N. Jadhav, B.N. Pandey, R.S. Ningthoujam, Dalton Trans. 42, 4885–4896 (2013)

    Article  CAS  PubMed  Google Scholar 

  49. J. Liu, W. Zuo, W. Zhang, J. Liu, Z.Y. Wang, Z.Y. Yang, B.D. Wang, Nanoscale 6, 11473–11478 (2014)

    Article  CAS  PubMed  Google Scholar 

  50. D.J. Zhang, D.H. Tang, X.M. Wang, Z.A. Qiao, Y.T. Li, Y.L. Liu, Q.S. Huo, Dalton Trans. 40, 9313–9319 (2011)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work is financially supported by the Key Scientific and Technological Project of Henan Province (172102410024), the National Natural Science Foundation of China (Nos. 21401218, 51572303), the Innovation Scientists and Technicians Troop Construction Projects of Henan Province (2013259), the Program for Innovative Research Team (in Science and Technology) in University of Henan Province (No. 14IRTSTHN009).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Qing-Feng Li or Zhenling Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 880 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, T., Hu, B., Huang, J. et al. Luminescent mesoporous hybrid materials grafted with lanthanide complexes synthesized by Michael-like addition reaction. J Porous Mater 26, 567–574 (2019). https://doi.org/10.1007/s10934-018-0656-6

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-018-0656-6

Keywords

Navigation