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Photocatalytic activity of pyrazinoporphyrin in the presence of gold nanoparticles and nanoclusters

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Abstract

The effect of gold nanoparticles and nanoclusters on the catalytic activity of dicarboxy-substituted pyrazinoporphyrin was studied using the photooxidation reaction of 1,5-dihydr-oxynaphthalene as an example. Annelation of the pyrazine heterocycle at β-positions of porphyrin leads to an increased photocatalytic activity compared to that of tetrakis-(4-butoxyphenyl)-porphyrin, a similar unmodified macroheterocyclic photosensitizer. The presence of gold nanoparticles in the catalytic system leads to an increased rate of photocatalyzed oxidation of 1,5-dihydroxynaphthalene, while this effect is not observed in the case of gold nanoclusters. Analysis of the luminescence spectra of the obtained porphyrin in the presence of gold nanoparticles showed that an increase in the concentration of nanoparticles results in the quenching of luminescence, which indicates an electron interaction between the nanoparticles and the photosensitizer. At the same time, no quenching is observed in the presence of porphyrin for gold nanoclusters with intrinsic luminescence, which indirectly indicates the absence of this interaction. The obtained spectral data are consistent with those of earlier studies on the effect of gold nanoparticles and nanoclusters on the photocatalytic activity of porphyrins.

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References

  1. J. You, Y. Guo, R. Guo and X. Liu, Chem. Eng. J., 2019, 373, 624–641.

    Article  CAS  Google Scholar 

  2. J. J. Rueda-Marquez, I. Levchuk, P. Fernández Ibañez, M. Sillanpää, J. Clean. Prod., 2020, 258, 120694.

    Article  CAS  Google Scholar 

  3. C. Gao, J. Low, R. Long, T. Kong, J. Zhu, Y. Xiong, Chem. Rev., 2020, 120, 12175–12216.

    Article  CAS  PubMed  Google Scholar 

  4. A. B. Djurišić, Y. He, A. M. C. Ng, APL Mater., 2020, 8, 030903.

    Article  Google Scholar 

  5. O. I. Koifman, T. A. Ageeva, Russ. Chem. Bull., 2015, 64, 2001.

    Article  CAS  Google Scholar 

  6. R. Costa de Silva, L. Oliveira da Silva, A. de Andrade Bartolomeu, T. J. Brocksom, K. T. de Oliveira, Beilstein J. Org. Chem., 2020, 16, 917–955.

    Article  Google Scholar 

  7. Y. Chen, Z. Huang, L. Wang, in Phthalocyanines and Some Current Applications, InTech, 2017.

  8. A. M. Huerta-Flores, G. Bengasi, K. Baba, N. D. Boscher, ACS Appl. Energy Mater., 2020, 3, 9848–9855.

    Article  CAS  Google Scholar 

  9. L. Wang, H. Fan, F. Bai, MRS Bull., 2020, 45, 49–56.

    Article  Google Scholar 

  10. L.-L. Li, E. W.-G. Diau, Chem. Soc. Rev., 2013, 42, 291–304.

    Article  CAS  PubMed  Google Scholar 

  11. J.-F. Longevial, S. Clément, J. A. Wytko, R. Ruppert, J. Weiss, S. Richeter, Chem.—Eur. J., 2018, 24, 15442–15460.

    Article  CAS  PubMed  Google Scholar 

  12. A. Farokhi, H. Hosseini-Monfared, New J. Chem., 2016, 40, 5032–5043.

    Article  CAS  Google Scholar 

  13. I. P. Beletskaya, V. S. Tyurin, A. Uglov, C. Stern, R. Guilard, in Handbook of Porphyrin Science, Eds R. Guilard, K. M. Kadish, K. M. Smith, World Scientific Publishing, Singapore, 2012, pp. 81–279.

  14. I. P. Beletskaya, V. S. Tyurin, A. Y. Tsivadze, R. Guilard, C. Stern, Chem. Rev., 2009, 109, 1659–1713.

    Article  CAS  PubMed  Google Scholar 

  15. S. Shao, V. Rajendiran, J. F. Lovell, Coord. Chem. Rev., 2019, 379, 99–120.

    Article  CAS  PubMed  Google Scholar 

  16. V. V Arslanov, M. A. Kalinina, E. V Ermakova, O. A. Raitman, Y. G. Gorbunova, O. E. Aksyutin, A. G. Ishkov, V. A. Grachev, A. Y. Tsivadze, Russ. Chem. Rev., 2019, 88, 775–799.

    Article  CAS  Google Scholar 

  17. N. G. Bichan, E. N. Ovchenkova, Russ. Chem. Bull., 2021, 70, 239–275.

    Article  CAS  Google Scholar 

  18. Z. Cao, S. B. Zacate, X. Sun, J. Liu, E. M. Hale, W. P. Carson, S. B. Tyndall, J. Xu, X. Liu, X. Liu, C. Song, J. Luo, M.-J. Cheng, X. Wen, W. Liu, Angew. Chem., Int. Ed., 2018, 130, 12857–12861.

    Article  Google Scholar 

  19. K. Bera, S. Maiti, M. Maity, C. Mandal, N. C. Maiti, ACS Omega, 2018, 3, 4602–4619.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. A. Shinohara, H. Shinmori, Bull. Chem. Soc. Jpn., 2016, 89, 1341–1343.

    Article  CAS  Google Scholar 

  21. O. Penon, M. J. Marín, D. A. Russell, L. Pérez-García, J. Colloid Interface Sci., 2017, 496, 100–110.

    Article  CAS  PubMed  Google Scholar 

  22. K. Záruba, J. Králová, P. Řezanka, P. Poučková, L. Veverková, V. Král, Org. Biomol. Chem., 2010, 8, 3202.

    Article  PubMed  Google Scholar 

  23. A. J. Shaikh, F. Rabbani, T. A. Sherazi, Z. Iqbal, S. Mir, S. A. Shahzad, J. Phys. Chem. A, 2015, 119, 1108–1116.

    Article  CAS  PubMed  Google Scholar 

  24. J. Bhaumik, G. Gogia, S. Kirar, L. Vijay, N. S. Thakur, U. C. Banerjee, J. K. Laha, New J. Chem., 2016, 40, 724–731.

    Article  CAS  Google Scholar 

  25. D. P. Cormode, J. J. Davis, P. D. Beer, J. Inorg. Organomet. Polym. Mater., 2008, 18, 32–40.

    Article  CAS  Google Scholar 

  26. I. Sebarchievici, B. O. Tăranu, M. Birdeanu, S. F. Rus, E. Fagadar-Cosma, Appl. Surf. Sci., 2016, 390, 131–140.

    Article  CAS  Google Scholar 

  27. D. Conklin, S. Nanayakkara, T.-H. Park, M. F. Lagadec, J. T. Stecher, M. J. Therien, D. A. Bonnell, Nano Lett., 2012, 12, 2414–2419.

    Article  CAS  PubMed  Google Scholar 

  28. A. Kotiaho, R. M. Lahtinen, N. V. Tkachenko, A. Efimov, A. Kira, H. Imahori, H. Lemmetyinen, Langmuir, 2007, 23, 13117–13125.

    Article  CAS  PubMed  Google Scholar 

  29. K. P. Birin, I. A. Abdulaeva, D. A. Polivanovskaya, A. A. Sinel’shchikova, L. I. Demina, A. E. Baranchikov, Yu. G. Gorbunova, A. Yu. Tsivadze, Russ. J. Inorg. Chem., 2021, 66, 193.

    Article  CAS  Google Scholar 

  30. I. A. Abdulaeva, K. P. Birin, Y. G. Gorbunova, A. Y. Tsivadze, A. Bessmertnykh-Lemeune, J. Porphyr. Phthalocyanines, 2018, 22, 619–631.

    Article  CAS  Google Scholar 

  31. I. A. Abdulaeva, K. P. Birin, A. A. Sinelshchikova, M. S. Grigoriev, K. A. Lyssenko, Y. G. Gorbunova, A. Y. Tsivadze, A. Bessmertnykh-Lemeune, CrystEngComm, 2019, 21, 1488–1498.

    Article  CAS  Google Scholar 

  32. I. A. Abdulaeva, K. P. Birin, A. Bessmertnykh-Lemeune, A. Y. Tsivadze, Y. G. Gorbunova, Coord. Chem. Rev., 2020, 407, 213108.

    Article  CAS  Google Scholar 

  33. I. A. Abdulaeva, D. A. Polivanovskaia, K. P. Birin, Y. G. Gorbunova, A. Y. Tsivadze, Mendeleev Commun., 2020, 30, 162–164.

    Article  CAS  Google Scholar 

  34. K. P. Birin, I. A. Abdulaeva, D. A. Polivanovskaia, A. G. Martynov, A. V. Shokurov, Y. G. Gorbunova, A. Y. Tsivadze, Dyes and Pigments, 2021, 186, 109042.

    Article  CAS  Google Scholar 

  35. K. P. Birin, I. A. Abdulaeva, A. I. Poddubnaya, Y. G. Gorbunova, A. Y. Tsivadze, Dyes and Pigments, 2020, 181, 108550.

    Article  CAS  Google Scholar 

  36. K. P. Birin, A. I. Poddubnaya, E. V. Isanbaeva, Y. G. Gorbunova, A. Y. Tsivadze, J. Porphyr. Phthalocyanines, 2017, 21, 406.

    Article  CAS  Google Scholar 

  37. I. A. Abdulaeva, K. P. Birin, D. A. Polivanovskaia, Y. G. Gorbunova, A. Y. Tsivadze, RSC Adv., 2020, 10, 42388–42399.

    Article  CAS  Google Scholar 

  38. W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, Elsevier, Butterworth—Heinemann, 2009.

    Google Scholar 

  39. K. P. Birin, A. I. Poddubnaya, I. A. Abdulaeva, Y. G. Gorbunova, A. Y. Tsivadze, Dyes and Pigments, 2018, 156, 243–249.

    Article  CAS  Google Scholar 

  40. I. A. Abdulaeva, K. P. Birin, J. Michalak, A. Romieu, C. Stern, A. Bessmertnykh-Lemeune, R. Guilard, Y. G. Gorbunova, A. Y. Tsivadze, New J. Chem., 2016, 40, 5758–5774.

    Article  CAS  Google Scholar 

  41. K. P. Birin, Y. G. Gorbunova, A. Y. Tsivadze, RSC Adv., 2015, 5, 67242–67246.

    Article  CAS  Google Scholar 

  42. M. J. Crossley, L. G. King, I. A. Newsom, C. S. Sheehan, J. Chem. Soc., Perkin Trans. 1, 1996, 2675–2684.

  43. M. J. Crossley, J. A. Mcdonald, J. Chem. Soc. Perkin Trans. 1, 1999, 2429–2431.

  44. M. Lo, J.-F. Lefebvre, N. Marcotte, C. Tonnele, D. Beljonne, R. Lazzaroni, S. Clement, S. Richeter, Chem. Commun., 2012, 48, 3460–3462.

    Article  CAS  Google Scholar 

  45. M. J. Crossley, C. S. Sheehan, T. Khoury, J. R. Reimers, P. J. Sintic, New J. Chem., 2008, 32, 340–352.

    Article  CAS  Google Scholar 

  46. J. Sun, J. Zhao, H. Guo, W. Wu, Chem. Commun., 2012, 48, 4169.

    Article  CAS  Google Scholar 

  47. J. Park, D. Feng, S. Yuan, H. Zhou, Angew. Chem., Int. Ed., 2015, 54, 430–435.

    Article  CAS  Google Scholar 

  48. J. J. Storhoff, R. Elghanian, R. C. Mucic, C. A. Mirkin, R. L. Letsinger, J. Am. Chem. Soc., 1998, 120, 1959–1964.

    Article  CAS  Google Scholar 

  49. H. Kawasaki, H. Yamamoto, H. Fujimori, R. Arakawa, Y. Iwasaki, M. Inada, Langmuir, 2010, 26, 5926–5933.

    Article  CAS  PubMed  Google Scholar 

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Funding

This work was financially supported by the Russian Foundation for Basic Research (Project No. 19-33-70036_mol_a_mos).

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Authors and Affiliations

  1. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Build. 4, 31 Leninsky prosp., 119071, Moscow, Russian Federation

    D. A. Polivanovskaia, K. P. Birin, A. A. Averin, Yu. G. Gorbunova & A. Yu. Tsivadze

  2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    Yu. G. Gorbunova & A. Yu. Tsivadze

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  1. D. A. Polivanovskaia
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  2. K. P. Birin
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Correspondence to K. P. Birin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2100–2109, November, 2021.

The authors are grateful to the Center for Collective Use of Physical Methods of Investigation of the A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences for the equipment provided for carrying out analytical research.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Polivanovskaia, D.A., Birin, K.P., Averin, A.A. et al. Photocatalytic activity of pyrazinoporphyrin in the presence of gold nanoparticles and nanoclusters. Russ Chem Bull 70, 2100–2109 (2021). https://doi.org/10.1007/s11172-021-3321-1

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  • DOI: https://doi.org/10.1007/s11172-021-3321-1

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