Skip to main content
Log in

A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines

  • Article
  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A triformylphloroglucinol-based A3B2-typed covalent organic polymer(TFG-BPTH) was successfully constructed by the condensation reaction of triformylphloroglucinol(TFG) and 2,5-bis(2-propynyloxy)terephthalo-hydrazide(BPTH) under solvothermal conditions. The structure of the TFG-BPTH was confirmed by spectra techniques including FTIR and solid-state 13C CP/MAS NMR spectroscopy. The mophological features of TFG-BPTH were analyzed using scanning electron microscopy(SEM) and transmission electron microscopy(TEM). The TFG-BPTH possessed good thermal and chemical stability, and exhibited good photocatalytic activity as a metal-free heterogeneous catalyst for oxidation of amines to valuable imines under visible light irradiation using O2 as green oxidant. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least five cycles without any observable change in structure and catalytic activity.

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.

Similar content being viewed by others

References

  1. Kou J., Lu C., Wang J., Chen Y., Xu Z., Varma R.S., Chem. Rev., 2017, 117, 1445

    CAS  PubMed  Google Scholar 

  2. Dau H., Zaharieva I., Acc. Chem. Res., 2009, 42, 1861

    CAS  PubMed  Google Scholar 

  3. Fujishima A., Honda K., Nature, 1972, 238, 37

    CAS  PubMed  Google Scholar 

  4. Wenderich K., Mul G., Chem. Rev., 2016, 116, 14587

    CAS  PubMed  Google Scholar 

  5. Izumi Y., Coord. Chem. Rev., 2013, 257, 171

    CAS  Google Scholar 

  6. Zhang B., Li J., Zhang B., Chong R., Li R., Yuan B., Lu S., Li C., J. Catal., 2015, 332, 95

    CAS  Google Scholar 

  7. Xiang Z., Xue Y., Cao D., Huang L., Chen J., Dai L., Angew. Chem. Int. Ed., 2014, 53, 2433

    CAS  Google Scholar 

  8. Kim M. S., Lee W. J., Peak S. M., Park J. K., ACS Appl. Mater. Interfaces, 2018, 10, 32102

    CAS  PubMed  Google Scholar 

  9. Zhang S., Chang C., Huang Z., Ma Y., Gao W., Li J., Qu Y., ACS Catal., 2015, 5, 6481

    CAS  Google Scholar 

  10. Liu Y., Zhang P., Tian B., Zhang J., ACS Appl. Mater. Interfaces, 2015, 7, 13849

    CAS  PubMed  Google Scholar 

  11. Sang N., Zhan C., Cao D., J. Mater. Chem. A., 2015, 3, 92

    CAS  Google Scholar 

  12. Wei P. F., Qi M. Z., Wang Z. P., Ding S. Y., Yu W., Liu Q., Wang L. K., Wang H. Z., An W. K., Wang W., J. Am. Chem. Soc., 2018, 140, 4623

    CAS  PubMed  Google Scholar 

  13. Chaoui N., Trunk M., Dawson R., Schmidt J., Thomas A., Chem. Soc. Rev., 2017, 46, 3302

    CAS  PubMed  Google Scholar 

  14. Wang Z. J., Ghasimi S., Landfester K., Zhang K. A., Chem. Commun., 2014, 50, 8177

    CAS  Google Scholar 

  15. Wang Z. J., Garth K., Ghasimi S., Landfester K., Zhang K. A., ChemSusChem, 2015, 8, 3459

    CAS  PubMed  Google Scholar 

  16. Li Z., Zhi Y., Shao P., Xia H., Li G., Feng X., Chen X., Shi Z., Liu X., Appl. Catal. B: Environ., 2019, 245, 334

    CAS  Google Scholar 

  17. Luo J., Zhang X., Zhang J., ACS Catal., 2015, 5, 2250

    CAS  Google Scholar 

  18. Beatty J. W., Stephenson C. R., Acc. Chem. Res., 2015, 48, 1474

    CAS  PubMed  PubMed Central  Google Scholar 

  19. Liu W., Su Q., Ju P., Guo B., Zhou H., Li G., Wu Q., ChemSus-Chem, 2017, 10, 664

    CAS  Google Scholar 

  20. Liu W., Wu S., Su Q., Guo B., Ju P., Li G., Wu Q., J. Mater. Sci., 2019, 54, 1205

    CAS  Google Scholar 

  21. Ju P., Wu S., Su Q., Li X., Liu Z., Li G., Wu Q., J. Mater. Chem. A., 2019, 7, 2660

    CAS  Google Scholar 

  22. Cui X., Li Y., Dong W., Liu D., Duan Q., React. Func. Polym., 2020 154, 104633

    CAS  Google Scholar 

  23. Stoppiello C. T., Isla H., Martínez-Abadía M., Fay M. W., Parmenter C. D. J., Roe M. J., Lerma-Berlanga B., Martí-Gastaldo C., Mateo-Alonso A., Khlobystov A. N., Nanoscale, 2019, 11, 2848

    CAS  PubMed  Google Scholar 

  24. Chai Y., Zhang L., Liu Q., Yang F., Dai W. L., ACS Sustainable Chem. Eng., 2018, 6, 10526

    CAS  Google Scholar 

  25. Layer R. W., Chem. Rev., 1963, 63, 489

    CAS  Google Scholar 

  26. Zhang N., Li X., Ye H., Chen S., Ju H., Liu D., Lin Y., Ye W., Wang C., Xu Q., Zhu J., Song L., Jiang J., Xiong Y., J. Am. Chem. Soc., 2016, 138, 8928

    CAS  PubMed  Google Scholar 

  27. Chen B., Wang L., Gao S., ACS Catal., 2015, 5, 5851

    CAS  Google Scholar 

  28. Yang X. J., Chen B., Li X. B., Zheng L. Q., Wu L. Z., Tung C. H., Chem. Commun., 2014, 50, 6664

    CAS  Google Scholar 

  29. Ding Z. D., Wang Y. X., Xi S. F., Li Y., Li Z., Ren X., Gu Z. G., Chem. Eur. J., 2016, 22, 17029

    CAS  PubMed  Google Scholar 

  30. Kandambeth S., Mallick A., Lukose B., Mane M. V., Heine T., Banerjee R., J. Am Chem. Soc., 2012, 134, 19524

    CAS  PubMed  Google Scholar 

  31. Xu Q., Tao S., Jiang Q., Jiang D., Angew. Chem. Int. Ed., 2020, 59, 4557

    CAS  Google Scholar 

  32. Mitra S., Sasmal H., Kundu T., Kandambeth S., Illath K., Diaz D., Banerjee R., J. Am. Chem. Soc., 2017, 139, 4513

    CAS  PubMed  Google Scholar 

  33. Yao B., Li J., Huang N., Kan J., Qiao L., Ding L., Li F., Dong Y., ACS Appl. Mater. Interfaces, 2018, 10, 20448

    CAS  PubMed  Google Scholar 

  34. Zhao C., Diercks C. S., Zhu C., Hanikel N., Pei X., Yaghi O. M., J. Am. Chem. Soc., 2018, 140, 16438

    CAS  PubMed  Google Scholar 

  35. Spitler E. L., Dichtel W. R., Nat. Chem., 2010, 2, 672

    CAS  PubMed  Google Scholar 

  36. Skubi K., Blum T., Yoon T., Chem. Rev., 2016, 116, 10035

    CAS  PubMed  PubMed Central  Google Scholar 

  37. Battula V. R., Singh H., Kumar S., Bala I., Pal S. K., Kailasam K., ACS Catal., 2018, 8, 6751

    CAS  Google Scholar 

  38. Zhou C., Shi R., Shang L., Wu L. Z., Tung C. H., Zhang T., Nano Research, 2018, 11, 3462

    CAS  Google Scholar 

  39. Zhou C., Shi R., Shang L., Zhao Y., Waterhouse G. I. N., Wu L. Z., Tung C. H., Zhang T., ChemPlusChem, 2017, 82, 181

    CAS  PubMed  Google Scholar 

  40. Huang W., Ma B. C., Lu H., Li R., Wang L., Landfester K., Zhang K. A. I., ACS Catal., 2017, 7, 5438

    CAS  Google Scholar 

  41. Ghosh S., Kouam N. A., Ramos L., Remita S., Dazzi A., Besseau A. D., Beaunier P., Goubard F., Aubert P. H., Remita H., Nat. Mater., 2015, 14, 505

    CAS  PubMed  Google Scholar 

  42. Su C., Tandiana R., Tian B., Sengupta A., Tang W., Su J., Loh K. P., ACS Catal., 2016, 6, 359

    Google Scholar 

  43. Wang Z. J., Ghasimi S., Landfester K., Zhang K. A. I., Adv. Mater., 2015, 27, 6265

    CAS  PubMed  Google Scholar 

  44. Raza F., Park J. H., Lee H. R., Kim H. I., Jeon S. J., Kim J. H., ACS Catal., 2016, 6, 2754

    CAS  Google Scholar 

  45. Wang Z., Garth K., Ghasimi S., Landfester K., Zhang K., ChemSusChem, 2015, 8, 3459

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Qing Su or Qiaolin Wu.

Additional information

Supported by the National Natural Science Foundation of China(No.51703076).

Supporting Information

40242_2020_8008_MOESM1_ESM.pdf

A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, X., Su, Q., Liu, Z. et al. A Triformylphloroglucinol-based Covalent Organic Polymer: Synthesis, Characterization and Its Application in Visible-light-driven Oxidative Coupling Reactions of Primary Amines. Chem. Res. Chin. Univ. 36, 1017–1023 (2020). https://doi.org/10.1007/s40242-020-8008-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-020-8008-x

Keywords

Navigation