Spectral Studies of Coordination of 1-Methyl-2-(pyridin-4-yl)-3,4-fullero[60]pyrrolidine by Highly Substituted Cobalt(II) Porphyrin

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A new dendrimeric cobalt(II) complex CoP has been obtained when reacting (5,15-bis[3,5-bis(tert-butyl)phenyl]-10,20-bis{4,6-bis[3,5-bis(3,6-di-tert-butylcarbazole-9-yl)phenoxy]pyrimidin-5-yl}porphine with Co(AcO)2·4H2O. The process of two-step two-way coordination of 1-methyl-2-(pyridin-4'-yl)-3,4-fullero[60]pyrrolidine (PyC60) with cobalt(II) porphyrin ends with the formation of a stable 1 : 2 complex, a triad of composition (PyC60)2CoP. The process has been completely kinetically described using UV-vis and fluorescent spectroscopy data. The stability constant (K) of the coordination complex is (9.9 ± 2.4) × 108 L2 mol–2 (log K = 9.0). The chemical structure of the triad has been determined by UV-vis, 1H NMR, and IR spectroscopy. The effect of PyC60 fluorescence quenching in the triad has been found and studied, and the static mechanism of the quenching process has been substantiated. The result can be used in optoelectronics to optimize the structures of donor–acceptor systems with the property of photoinduced electron transfer.

About the authors

N. G. Bichan

Krestov Institute of Solution Chemistry, Russian Academy of Sciences

Email: bng@isc-ras.ru
153045, Ivanovo, Russia

V. A. Mozgova

Krestov Institute of Solution Chemistry, Russian Academy of Sciences

Email: bng@isc-ras.ru
153045, Ivanovo, Russia

E. N. Ovchenkova

Krestov Institute of Solution Chemistry, Russian Academy of Sciences

Email: bng@isc-ras.ru
153045, Ivanovo, Russia

M. S. Gruzdev

Krestov Institute of Solution Chemistry, Russian Academy of Sciences

Email: bng@isc-ras.ru
153045, Ivanovo, Russia

T. N. Lomova

Krestov Institute of Solution Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: bng@isc-ras.ru
153045, Ivanovo, Russia

References

  1. Sutton L.R., Scheloske M., Pirner K.S. et al. // J. Am. Chem. Soc. 2004. V. 126. № 33. P. 10370. https://doi.org/10.1021/ja048983d
  2. D'Souza F., Ito O. // Coord. Chem. Rev. 2005. V. 249. № 13. P. 1410. https://doi.org/10.1016/j.ccr.2005.01.002
  3. Миронов А.Ф. // Макрогетероциклы. 2011. Т. 4. № 3. С. 186.
  4. Nikolaou V., Charisiadis A., Stangel C. et al. // J. Carbon Res. 2019. V. 5. № 3. P. 57. https://doi.org/10.3390/c5030057
  5. Лебедева В.С., Миронова Н.А., Рузиев Р.Д. и др. // Макрогетероциклы. 2018. Т. 11. № 4. С. 339. https://doi.org/10.6060/mhc180690l
  6. Моторина Е.В., Климова И.А., Бичан Н.Г. и др. // Журн. неорган. химии. 2022. Т. 67. № 12. С. 1779. https://doi.org/10.31857/S0044457X22600712
  7. Цивадзе А.Ю., Чернядьев А.Ю. // Журн. неорган. химии. 2020. Т. 65. № 11. С. 1469. https://doi.org/10.31857/S0044457X20110197
  8. Loiseau F., Campagna S., Hameurlaine A. et al. // J. Am. Chem. Soc. 2005. V. 127. № 32. P. 11352. https://doi.org/10.1021/ja0514444
  9. Organista-Mateos U., Martínez-Klimov M.E., Pedro-Hernández L.D. et al. // J. Photochem. Photobiol. A: Chemistry. 2017. V. 343. P. 58. https://doi.org/10.1016/j.jphotochem.2017.04.020
  10. Maes W., Dehaen W. // Eur. J. Org. Chem. 2009. V. 2009. № 28. P. 4719. https://doi.org/10.1002/ejoc.200900512
  11. Albrecht K., Kasai Y., Kuramoto Y. et al. // Chem. Commun. 2013. V. 49. № 9. P. 865. https://doi.org/10.1039/c2cc36451d
  12. Bichan N.G., Ovchenkova E.N., Ksenofontov A.A. et al. // Dyes Pigm. 2022. V. 204. P. 110470. https://doi.org/10.1016/j.dyepig.2022.110470
  13. Gruzdev M.S., Chervonova U.V., Ksenofontov A.A. et al. // Opt. Mater. 2021. V. 122. P. 111661. https://doi.org/10.1016/j.optmat.2021.111661
  14. Сюткин Р.В., Абашев Г.Г., Шкляева Е.В. и др. // Журн. орг. химии. 2011. Т. 47. № 4. С. 532.
  15. Груздев М.С., Червонова У.В., Венедиктов Е.А. и др. // Журн. общ. химии. 2015. Т. 85. № 6. С. 964.
  16. Staderini M., Vanni S., Baldeschi A.C. et al. // Eur. J. Med. Chem. 2023. V. 245. P. 114923. https://doi.org/10.1016/j.ejmech.2022.114923
  17. Banerjee A., Kundu S., Bhattacharyya A. et al. // Org. Chem. Frontiers. 2021. V. 8. № 11. P. 2710. https://doi.org/10.1039/d1qo00092f
  18. Çelik F., Aydın A., Bektaş K.İ. et al. // Russ. J. Gen. Chem. 2022. V. 92. № 10. P. 2145. https://doi.org/10.1134/s1070363222100279
  19. Скрылькова А.С., Егоров Д.М., Тарабанов Р.В. // Журн. общ. химии. 2021. Т. 91. № 91. С. 1627. https://doi.org/10.31857/S0044460X21100206
  20. Devi E.R., Sreenivasulu R., Rao M.V.B. et al. // Russ. J. Gen. Chem. 2021. V. 91. № 6. P. 1105. https://doi.org/10.1134/s1070363221060189
  21. Xu T., Lu R., Liu X. et al. // Org. Lett. 2007. V. 9. № 5. P. 797. https://doi.org/10.1021/ol062979k
  22. El-Khouly M.E., Kang E.S., Kay K.-Y. et al. // Chem. Eur. J. 2007. V. 13. № 10. P. 2854. https://doi.org/10.1002/chem.200601254
  23. Guo Q., Chen L., Pan S. et al. // Dalton Trans. 2018. V. 47. № 37. P. 13164. https://doi.org/10.1039/c8dt02275e
  24. Ovchenkova E.N., Bichan N.G., Gruzdev M.S. et al. // New J. Chem. 2021. V. 45. № 20. P. 9053. https://doi.org/10.1039/d1nj00980j
  25. Subedi D.R., Jang Y., Ganesan A. et al. // J. Porphyrins Phthalocyanines. 2021. V. 25. № 05–06. P. 533. https://doi.org/10.1142/s1088424621500449
  26. Ovchenkova E.N., Motorina E.V., Bichan N.G. et al. // J. Organomet. Chem. 2022. V. 977. P. 122458. https://doi.org/10.1016/j.jorganchem.2022.122458
  27. Бичан Н.Г., Овченкова Е.Н., Груздев М.С. и др. // Журн. структур. химии. 2018. Т. 59. № 3. С. 734. https://doi.org/10.26902/JSC20180332
  28. Бичан Н.Г., Овченкова Е.Н., Мозгова В.А. и др. // Журн. неорган. химии. 2019. Т. 64. № 5. С. 490. https://doi.org/10.1134/S0044457X19050027
  29. Бичан Н.Г., Овченкова Е.Н., Мозгова В.А. и др. // Журн. физ. химии. 2020. Т. 94. № 6. С. 873.
  30. Bichan N.G., Ovchenkova E.N., Kudryakova N.O. et al. // J. Coord. Chem. 2017. V. 70. № 14. P. 2371. https://doi.org/10.1080/00958972.2017.1335867
  31. Bichan N.G., Ovchenkova E.N., Ksenofontov A.A. et al. // J. Mol. Liq. 2021. V. 326. P. 115306. https://doi.org/10.1016/j.molliq.2021.115306
  32. Bichan N.G., Ovchenkova E.N., Mozgova V.A. et al. // Polyhedron. 2021. V. 203. P. 115223. https://doi.org/10.1016/j.poly.2021.115223
  33. Bichan N.G., Ovchenkova E.N., Mozgova V.A. et al. // Molecules. 2022. V. 27. P. 8900. https://doi.org/10.3390/molecules27248900
  34. Lomova T.N., Motorina E.V., Klyuev M.V. // Macroheterocycles. 2013. V. 6. № 4. P. 327. https://doi.org/10.6060/mhc130644l
  35. Liu Y., Bian Y., Zhang Y. et al. // J. Phys. Chem. Lett. 2021. V. 12. № 22. P. 5349. https://doi.org/10.1021/acs.jpclett.1c01123
  36. Ma B., Sun Y.-P. // J. Chem. Soc., Perkin Trans. 2. 1996. № 10. P. 2157. https://doi.org/10.1039/p29960002157
  37. Brites M.J., Santos C., Nascimento S. et al. // New J. Chem. 2006. V. 30. № 7. P. 1036. https://doi.org/10.1039/b601649a
  38. Luo C., Fujitsuka M., Watanabe A. et al. // J. Chem. Soc., Faraday Trans. 1998. V. 94. № 4. P. 527. https://doi.org/10.1039/a706672d
  39. Ovchenkova E.N., Bichan N.G., Tsaturyan A.A. et al. // J. Phys. Chem. C. 2020. V. 124. P. 4010. https://doi.org/10.1021/acs.jpcc.9b11661
  40. Thornton D.A., Verhoeven P.F.M. // Spectrosc. Lett. 1995. V. 28. № 4. P. 587. https://doi.org/10.1080/00387019508009902
  41. Martin M.C., Du X., Kwon J. et al. // Phys. Rev. B. 1994. V. 50. № 1. P. 173. https://doi.org/10.1103/PhysRevB.50.173

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2.

Download (150KB)
Indexing metadata
3.

Download (120KB)
Indexing metadata
4.

Download (57KB)
Indexing metadata
5.

Download (240KB)
Indexing metadata
6.

Download (86KB)
Indexing metadata
7.

Download (82KB)
Indexing metadata

Copyright (c) 2023 Н.Г. Бичан, В.А. Мозгова, Е.Н. Овченкова, М.С. Груздев, Т.Н. Ломова

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies