Skip to main content
SpringerLink
Log in

Reusable photoresponsive Ag/AgCl nanocube-catalyzed one-pot synthesis of seleno[2,3-b]pyridine derivatives

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this study, a facile and rapid method was developed to synthesize intensely organoselenium compounds, namely ethylseleno[2,3-b]pyridine carboxylate, seleno[2,3-b]pyridine-2-carbonitrile and 2-benzoylseleno[2,3-b]pyridine derivatives from starting compound, 2-chloro-3-cyano-4,6-dimethylpyridine, in one-pot synthesis using Ag/AgCl nanoparticles (NPs) under visible light irradiation. Three different shapes of Ag/AgCl nanoparticles (nanospheres (NS), nanocubes (NC) and nanowires (NW)) were synthesized by controlling the concentration ratio between silver nitrate (AgNO3) and hydrochloric acid. The Ag/AgCl NPs were characterized using different tools such as scanning electron microscopy, UV–Vis spectrophotometry and X-ray diffraction. The catalytic activity of the photoresponsive Ag/AgCl nanoparticles with different morphology was evaluated towards organoselenium compounds production. The following rate order of seleno[2,3-b]pyridine derivatives production and organic dye degradation under visible light irradiation was Ag/AgCl-NC > Ag/AgCl-NW > Ag/AgCl-NS. The mechanism of the production of seleno[2,3-b]pyridine derivatives has been proposed. It is clearly shown from the results that high yield of selective organoselenium compounds (> 90%) was obtained under mild conditions with short reaction time and the photocatalytic activity of the prepared Ag/AgCl nanoparticles depends on their morphology.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 1

Similar content being viewed by others

References

  1. D. Wang, D. Astruc, Chem. Rev. 114, 6949 (2014)

    Article  CAS  Google Scholar 

  2. M.B. Gawande, Y. Monga, R. Zboril, R.K. Sharma, Coordin. Chem. Rev. 288, 118 (2015)

    CAS  Google Scholar 

  3. A.A. Herzing, C.J. Kiely, A.F. Carley, P. Landon, G.J. Hutchings, Science 321, 1331 (2008)

    Article  CAS  Google Scholar 

  4. Y.A. Attia, S. Abdel-Hafez, New J. Chem. 42(12), 9606 (2018)

    Article  CAS  Google Scholar 

  5. Y.A. Attia, Y.M.A. Mohamed, Appl. Organomet. Chem. 33(3), e4757 (2019)

    Article  Google Scholar 

  6. Y.M.A. Mohamed, Y.A. Attia, E.J. Solum, Res. Chem. Intermed. 44(12), 7173 (2018)

    Article  CAS  Google Scholar 

  7. Y.A. Attia, C.V. Vázquez, Y.M.A. Mohamed, Res. Chem. Intermed. 43(1), 203 (2017)

    Article  CAS  Google Scholar 

  8. Y. Attia, D. Buceta, C. Blanco-Varela, M. Mohamed, G. Barone, M.A. López-Quintela, J. Am. Chem. Soc. 136, 1182 (2014)

    Article  CAS  Google Scholar 

  9. Y.A. Attia, C.V. Vázquez, M.C. Blanco, D. Buceta, M.A. López-Quintela, Faraday Discuss. 191, 205 (2016)

    Article  CAS  Google Scholar 

  10. Y. Attia, D. Buceta, F. Requejo, L. Giovanetti, M.A. López-Quintela, Nanoscale 7, 11273 (2015)

    Article  CAS  Google Scholar 

  11. Y.A. Attia, Mater. Express 6(3), 211 (2016)

    Article  CAS  Google Scholar 

  12. E.V. Ratushnaya, Y.I. Kirova, M.A. Suchkov, B.I. Drevko, V.B. Borodulin, Pharm. Chem. J. 36(12), 652 (2002)

    Article  CAS  Google Scholar 

  13. C. Jacob, G. Giles, F. Fry, US Patent 2004, wo 200 4047925

  14. T. Maier, S. Scheiblich, H.S. Baltruschat, US Patent 2001, 11 064; Chem. Abstr. 2001, 135, 133440w

  15. S.A. Armstrong, J.M. Berge, P. Brown, J.S. Elder, A.K. Forrest, O.W. Hamprecht, R.L. Jarrest, PCT Int. Appl. 1999, WO 0071524; Chem. Abstr. 2001, 134, 17496

  16. Proctor and Gamble Ltd., US Patent 1966, 3 236733; Chem. Abstr., 1966, 64, 17364

  17. Rasching, US Patent 1960, 2 937 118; Chem. Abstr., 1966, 54, 17807

  18. S.H. Abdel-Hafez, S. Abdel-Mohsen, Y.A. El-Ossaily, Phosphorus Sulfur Silicon Relat. Elem. 181(10), 2297 (2006)

    Article  CAS  Google Scholar 

  19. S.H. Abdel-Hafez, R.A. Ahmed, M.A. Abdel-Azim, K.M. Hassan, J. Chem. Res. 2007(10), 580 (2007)

    Article  Google Scholar 

  20. S.H. Abdel-Hafez, R.A. Ahmed, M.A. Abdel-Azim, K.M. Hassan, J. Chem. Res. 2009(1), 56 (2009)

    Article  Google Scholar 

  21. J. Jiang, H. Li, L. Zhang, Chem. Eur. J. 18, 6360 (2012)

    Article  CAS  Google Scholar 

  22. P. Wang, B. Huang, X. Zhang, X. Qin, Y. Dai, Z. Wang, Z. Lou, ChemCatChem 3, 360 (2011)

    Article  Google Scholar 

  23. P. Wang, B. Huang, X. Zhang, X. Qin, H. Jin, Y. Dai, Z. Wang, J. Wei, J. Zhan, Sh Wang, J. Wang, M.-H. Whangbo, Chem. Eur. J. 15, 1821 (2009)

    Article  CAS  Google Scholar 

  24. T.J. Yan, H.W. Zhang, Q. Luo, Y.Y. Ma, H.X. Lin, J.M. You, Chem. Eng. J. 232, 564 (2013)

    Article  CAS  Google Scholar 

  25. P. Wang, B. Huang, Z. Lou, X. Zhang, X. Qin, Y. Dai, Z. Zheng, X. Wang, Chem. Eur. J. 16, 538 (2010)

    Article  CAS  Google Scholar 

  26. H. Xu, H. Li, J. Xia, S. Yin, Z. Luo, L. Liu, L. Xu, A.C.S. Appl, Mater. Interfaces 3, 22 (2011)

    Article  CAS  Google Scholar 

  27. X. Lin, H. Liu, B. Guo, X. Zhang, J. Environ. Chem. Eng. 4(4), 4021 (2016)

    Article  CAS  Google Scholar 

  28. S.H. Im, Y.T. Lee, B. Wiley, Y. Xia, Angew. Chem. Int. Ed. 44(14), 2154 (2005)

    Article  CAS  Google Scholar 

  29. V.P. Litvinov, V.Y. Mortikov, Y.A. Sharanin, A.M. Shestopalov, Synthesis 1, 98 (1985)

    Article  Google Scholar 

  30. S. Kim, H. Chung, J.H. Kwon, H.G. Yoon, W. Kim, Bull. Korean Chem. Soc. 31(10), 2918 (2010)

    Article  CAS  Google Scholar 

  31. S.A. Ryndina, A.V. Kadushkin, N.P. Solov’eva, V.G. Granik, Russ. Chem. Bull. Int. Ed. 51(5), 854 (2002)

    Article  CAS  Google Scholar 

  32. A.M. Shestopalov, L.A. Rodinovskaya, A.A. Shestopalov, Tetrahedron 66(46), 8945 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgement

We would like to express special words of thanks with deepest appreciation to the team of this study. We would like to acknowledge RanaEssa, Eman Mohamed and AmanyKhalifa, NILES, Cairo University for useful participation in experimental research.

Funding

This research did not receive any specific grant from funding agencies in the public, commercial or not-for-profit sectors.

Author information

Authors and Affiliations

  1. National Institute of Laser Enhanced Sciences, Cairo University, Giza, 12613, Egypt

    Yasser Attia Attia

  2. Department of Chemistry, Faculty of Science, Assiut University, Assiut, 71516, Egypt

    Shams H. Abdel-Hafez

  3. Department of Chemistry, Faculty of Science, Taif University, Taif, 21974, Saudi Arabia

    Shams H. Abdel-Hafez

Authors
  1. Yasser Attia Attia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shams H. Abdel-Hafez
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yasser Attia Attia.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher's Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Attia, Y.A., Abdel-Hafez, S.H. Reusable photoresponsive Ag/AgCl nanocube-catalyzed one-pot synthesis of seleno[2,3-b]pyridine derivatives. Res Chem Intermed 46, 3165–3177 (2020). https://doi.org/10.1007/s11164-020-04143-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04143-6

Keywords

Search

Navigation