Skip to main content
SpringerLink
Log in

Synthesis, post-modification and catalytic properties of metal-organic framework NH2-MIL-53(Al)

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A postsynthetic modification method was used to prepare salicylaldehyde functionalized metal-organic frameworks through the nucleophilic addition of salicylaldehyde with the amine group present in the frameworks of NH2-MIL-53(Al). Hydroxyl groups were successfully grafted onto NH2-MIL-53(Al), and imine groups were formed. Importantly, these hydroxyl and imine groups of the resulting NH2-MIL-53(Al)-SA can be used as the anchoring group to stabilise Au3+ ions and Au0 nanoparticles(NPs). By doing this, Au3+ ions and Au0 NPs were successfully encapsulated in the cages of NH2-MIL-53(Al) by a simple impregnation method. The resulting gold functionalized NH2-MIL-53(Al) showed good catalytic activities in the one-pot synthesis of structurally divergent propargylamines by three-component coupling reactions of aldehydes, amines and alkynes. Various aromatic/aliphatic aldehydes, aromatic alkynes, and piperidine were able to undergo three-component coupling on NH2-MIL-53(Al)-Au. In addition, the catalyst NH2-MIL-53(Al)-Au was recovered easily by centrifugation and reused up to four times. Thus, it can be used for the environmentally friendly synthesis of propargylamines.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Zhou H. C., Long J. R., Yaghi O. M., Chem. Rev., 2012, 112, 673

    Article  CAS  Google Scholar 

  2. Lu T., Zhang L. C., Sun M. X., Deng D. Y., Su Y. Y., Lv Y., Anal. Chem., 2016, 88, 3413

    Article  CAS  Google Scholar 

  3. Eddaoudi M., Kim, J., Rosi N., Vodak D., Wachter J., O’Keeffe M., Yaghi O. M., Science, 2002, 295, 469

    Article  CAS  Google Scholar 

  4. Yaghi O. M., O’Keeffe M., Ockwig N. W., Chae H. K., Eddaoudi M., Kim J., Nature, 2003, 423, 705

    Article  CAS  Google Scholar 

  5. Hamon L., Serre C., Devic T., Loiseau T., Millange F., Férey G., Weireld G. D., J. Am. Chem. Soc., 2009, 131, 8775

    Article  CAS  Google Scholar 

  6. Li J. R., Sculley J., Zhou H. C., Chem. Rev., 2012, 112, 869

    Article  CAS  Google Scholar 

  7. Harbuzaru B. V., Corma A., Rey F., Atienzar P., Jorda J. L., García H., Ananias D., Carlos L. D., Rocha J., Angew. Chem. Int. Ed., 2008, 47, 1080

    Article  CAS  Google Scholar 

  8. Lu Y., Yan B., Liu J. L., Chem. Commun., 2014, 50, 9969

    Article  CAS  Google Scholar 

  9. Wan X. Y., Wu L. Q., Zhang L. C., Song H. J., Lv Y., Sens. Actuators B, 2015, 220, 614

    Article  CAS  Google Scholar 

  10. Taylor-Pashow K. M. L., Della R. J., Xie Z. G., Tran S., Lin W. B., J. Am. Chem. Soc., 2009, 131(40), 14261

    Article  CAS  Google Scholar 

  11. He C. B., Lu K. D., Liu D. M., Lin W. B., J. Am. Chem. Soc., 2014, 136, 5181

    Article  CAS  Google Scholar 

  12. Liu J., Zhang X. B., Yang J., Wang L., Appl. Organometal. Chem., 2014, 28, 198

    Article  CAS  Google Scholar 

  13. Liu L. L., Zhang X., Gao J. S., Xu C. M., Green Chem., 2012, 14, 1710

    Article  CAS  Google Scholar 

  14. Liu L. L., Zhang X., Rang S. M., Yang Y., Dai X. P., Gao J. S., Xu C. M., He J., RSC Adv., 2014, 4, 13093

    Article  CAS  Google Scholar 

  15. Banerjee M., Das S., Yoon M., Choi H. J., Hyun M. H., Park S. M., Seo G., Kim K., J. Am. Chem. Soc., 2009, 131, 7524

    Article  CAS  Google Scholar 

  16. Cheng X. Q., Liu M., Zhang A. F., Hu S., Song C. S., Zhang G. L., Guo X. W., Nanoscale, 2015, 7, 9738

    Article  CAS  Google Scholar 

  17. Garibay S. J., Wang Z. Q., Tanabe K. K., Cohen S. M., Inorg. Chem., 2009, 48, 7341

    Article  CAS  Google Scholar 

  18. Dugan E., Wang Z. Q., Okamura M., Medina A., Cohen S. M., Chem. Commun., 2008, 3366

    Google Scholar 

  19. Wang Z. Q., Cohen S. M., J. Am. Chem. Soc., 2007, 129, 12368

    Article  CAS  Google Scholar 

  20. Tanabe K. K., Wang Z. Q., Cohen S. M., J. Am. Chem. Soc., 2008, 130, 8508

    Article  CAS  Google Scholar 

  21. Wu Y. Z., Xu G. H., Liu W., Yang J., Wei F. D., Li L., Zhang W., Hu Q., Micropor. Mesopor. Mat., 2015, 210, 110

    Article  CAS  Google Scholar 

  22. Wittmann T., Siegel R., Reimer N., Milius W., Stock N., Senker J., Chem. Eur. J., 2015, 21(1), 314

    Article  CAS  Google Scholar 

  23. Xi F. G., Liu H., Yang N. N., Gao E. Q., Inorg. Chem., 2016, 55(10), 4701

    Article  CAS  Google Scholar 

  24. Zhang X., Zhang J. M., Hu Q., Cui Y. J., Yang Y., Qian G. D., Appl. Surf. Sci., 2015, 355, 814

    Article  CAS  Google Scholar 

  25. Li B. Y., Ma D. X., Zhang Y. L., Li G. H., Shi Z., Feng S. H., Zawo-rotko M. J., Ma S. Q., Chem. Mater., 2016, 28(13), 4781

    Article  CAS  Google Scholar 

  26. Huffman M. A., Yasuda N., De Camp A. E., Grabowski E. J. J., J. Org. Chem., 1995, 60, 1590

    Article  CAS  Google Scholar 

  27. Konishi M., Ohkuma H., Tsuno T., Oki T., J. Am. Chem. Soc., 1990, 112, 3715

    Article  CAS  Google Scholar 

  28. Hu A., Yee G. T., Lin W., J. Am. Chem. Soc., 2005, 125, 12486

    Article  Google Scholar 

  29. Gajengi A. L., Sasaki T., Bhanage B. M., Catal. Commun., 2015, 72, 174

    Article  CAS  Google Scholar 

  30. Tai X. S., Liu L. L., Yin J., J. Inorg. Organomet. Polym., 2014, 24(6), 1014

    Article  CAS  Google Scholar 

  31. Borah B. J., Borah S. J., Saikia K., Dutta D. K., Catal. Sci. Technol., 2014, 4(11), 4001

    Article  CAS  Google Scholar 

  32. Nasrollahzadeh M., Sajadi S. M., RSC Adv., 2015, 5(57), 46240

    Article  CAS  Google Scholar 

  33. Zhang X., Corma A., Angew. Chem. Int. Ed., 2008, 47, 4358

    Article  Google Scholar 

  34. Berrichi A., Bachir R., Benabdallah M., Choukchou-Braham N., Tetrahedron Lett., 2015, 56, 1302

    Article  CAS  Google Scholar 

  35. Abahmane L., Koehler J. M., Gross G. A., Chem. Eur. J., 2011, 17, 3005

    Article  CAS  Google Scholar 

  36. Liu L. L., Tai X. S., Liu M. F., Li Y. F., Feng Y. M., Sun X. R., CIESC Journal, 2015, 66(5), 1738

    CAS  Google Scholar 

  37. Villaverde G., Corma A., Iglesias M., Sánchez F., ACS Catal., 2012, 2(3), 399

    Article  CAS  Google Scholar 

  38. Lo V. K. Y., Liu Y., Wong M. K., Che C. M., Org. Lett., 2006, 8, 1529

    Article  CAS  Google Scholar 

  39. Chang Y. C., Kuo C. J., Li C. S., Liu C. H., J. Organomet. Chem., 2006, 691, 4982

    Article  CAS  Google Scholar 

  40. Wei C., Li Z., Li C. J., Org. Lett., 2003, 5, 4473

    Article  CAS  Google Scholar 

  41. Palchak Z. L., Lussier D. J., Pierce C. J., Larsen C. H., Green Chem., 2015, 17(3), 1802

    Article  CAS  Google Scholar 

  42. Hua P., Lei W., Chin. J. Chem., 2005, 23(8), 1076

    Article  Google Scholar 

  43. Tai X. S., Liu L. L., Open Materials Science Journal, 2014, 9(1), 1

    Article  Google Scholar 

  44. Gonzalez-Bejar M., Peters K., Hallett-Tapley G. L., Grenier M., Scaiano J. C., Chem. Commun., 2013, 49(17), 1732

    Article  CAS  Google Scholar 

  45. Liu L. L., Zhang X., Gao J. S., Xu C. M., Chin. J. Catal., 2012, 33(5), 833

    Google Scholar 

  46. Ishida T., Haruta M., Angew. Chem. Int. Ed., 2007, 46, 7154

    Article  CAS  Google Scholar 

  47. Zhang X., Xamena F. X. L., Corma A., J. Catal., 2009, 265, 155

    Article  CAS  Google Scholar 

  48. Gascon J., Aktay U., Hernandez-Alonso M. D., van Klink G. P. M., Kapteijn F., J. Catal., 2009, 261(1), 75

    Article  CAS  Google Scholar 

  49. Stavitski E., Pidko E. A., Couck S., Remy T., Hensen E. J. M., Weckhuysen B. M., Langmuir, 2011, 27, 3970

    Article  CAS  Google Scholar 

  50. Liu L. L., Tai X. S., Yu G. L., Guo H. M., Meng Q. G., Chem. Res. Chinese Universities, 2016, 32(3), 443

    Article  CAS  Google Scholar 

  51. Zhang L., Hu Y. H., J. Phys. Chem. C, 2010, 114, 2566

    Article  CAS  Google Scholar 

  52. Chang L. M., Li J. R., Duan X. Y., Liu W., Electrochimica Acta, 2015, 176, 956

    Article  CAS  Google Scholar 

  53. Zhang W., Wu Z. Y., Jing H. L., Yu S. H., J. Am. Chem. Soc., 2014, 136, 14385

    Article  CAS  Google Scholar 

  54. Liu R. L., Ji W. J., He T., Zhang Z. Q., Zhang J., Dang F. Q., Carbon, 2014, 76, 84

    Article  CAS  Google Scholar 

  55. Cheng X. Q., Zhang A. F., Hou K. K., Liu M., Wang Y. X., Song C. S., Zhang G. L., Guo X. W., Dalton Trans., 2013, 42, 13698

    Article  CAS  Google Scholar 

  56. Chen X. Y., Vinh-Thang H., Rodrigue D., Kaliaguine S., Ind. Eng. Chem. Res., 2012, 51, 6895

    Article  CAS  Google Scholar 

  57. Abedini R., Omidkhah M., Dorosti F., RSC Adv., 2014, 4, 36522

    Article  CAS  Google Scholar 

  58. Bromberg L., Su X., Hatton T. A., ACS Appl. Mater. Interfaces, 2013, 5, 5468

    Article  CAS  Google Scholar 

  59. Feijani E. A., Tavasoli A., Mahdavi H., Ind. Eng. Chem. Res., 2015, 54, 12124

    Article  Google Scholar 

  60. Liang H., Liu L., Yang H. X., Wei J. J., Yang Z. J., Yang Y. Z., Cryst. Eng. Comm., 2011, 13, 2445

    Article  CAS  Google Scholar 

  61. Zhang X., Shi H., Xu B.Q., Catal. Today, 2007, 122(3/4), 330

    Article  CAS  Google Scholar 

  62. Hutchings G. J., Hall M. S., Carley A. F., Landon P., Solsona B. E., Kiely C. J., Herzing A., Makkee M., Moulijn J. A., Overweg A., Fierro-Gonzalez J. C., Gates B. C., J. Catal., 2006, 242(1), 71

    Article  CAS  Google Scholar 

  63. Zhang X., Shi H., Xu B. Q., Angew. Chem. Int. Ed., 2005, 44, 7132

    Article  CAS  Google Scholar 

  64. Casaletto M. P., Longo A., Martorana A., Prestianni A., Venezia A. M., Surf. Interface Anal., 2006, 38, 215

    Article  CAS  Google Scholar 

  65. Zhang X., Corma A., Chem. Commun., 2007, 38(29), 3080

    Article  Google Scholar 

  66. Liu L. L., Tai X. S., Zhang N. N., Meng Q. G., Xin C. L., Reac. Kinet. Mech. Cat., 2016, 119, 335

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry & Chemical Engineering and Environmental Engineering, Weifang University, Weifang, 261061, P. R. China

    Lili Liu, Xishi Tai, Xiaojing Zhou & Lijuan Liu

Authors
  1. Lili Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xishi Tai
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiaojing Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lijuan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Lili Liu or Xishi Tai.

Additional information

Supported by the Promotive Research Fund for Young and Middle-aged Scientists of Shandong Province, China(No. BS2014CL021), the Project of Shandong Provincical Higher Educational Science and Technology Program, China(No.J14LC01) and the Technology Research and Development Program of Weifang, China(No.2014GX030).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, L., Tai, X., Zhou, X. et al. Synthesis, post-modification and catalytic properties of metal-organic framework NH2-MIL-53(Al). Chem. Res. Chin. Univ. 33, 231–238 (2017). https://doi.org/10.1007/s40242-017-6420-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-017-6420-7

Keywords

Search

Navigation