Synthesis, Structures, and Spectral Properties of Octa(2,6-difluorophenyl)tetraazaporphyrin and Its Cu(II) and Ni(II) Complexes

A. I. Rusanov; Русанов А. И.; N. V. Chizhova; Чижова Н. В.; A. E. Likhonina; Лихонина А. Е.; N. Zh. Mamardashvili; Мамардашвили Н. Ж.

doi:10.31857/S0044457X23600329

Synthesis, Structures, and Spectral Properties of Octa(2,6-difluorophenyl)tetraazaporphyrin and Its Cu(II) and Ni(II) Complexes

作者: Rusanov A.I.¹, Chizhova N.V.¹, Likhonina A.E.¹, Mamardashvili N.Z.¹
隶属关系:
1. Krestov Institute of Solutions Chemistry, Russian Academy of Sciences
期: 卷 68, 编号 8 (2023)
页面: 1050-1058
栏目: КООРДИНАЦИОННЫЕ СОЕДИНЕНИЯ
URL: https://rjmseer.com/0044-457X/article/view/665209
DOI: https://doi.org/10.31857/S0044457X23600329
EDN: https://elibrary.ru/HNDCUU
ID: 665209

如何引用文章

全文:

开放存取

##reader.subscriptionAccessGranted##
受限制的访问

订阅或者付费存取

详细
作者简介
参考
补充文件
统计

详细

Octa(2,6-difluorophenyl)tetraazaporphyrinate magnesium(II) has been treated with 96% sulfuric acid to obtain octa(2,6-difluorophenyl)tetraazaporphyrin. Coordination reactions of octa(2,6-difluorophenyl)tetraazaporphyrin and metal exchange of its magnesium complex with copper and nickel salts in dimethylformamide have been studied. Cu(II) and Ni(II) complexes with octa(2,6-difluorophenyl)tetraazaporphyrin have been synthesized. The resulting compounds have been identified by electron absorption, IR and 1H NMR spectroscopy, and mass spectrometry. The structures of the synthesized compounds were optimized by the DFT method. The fluorescence quantum yields of the studied compounds have been determined.

关键词

octa(2,6-difluorophenyl)tetraazaporphyrin Mg(II) Cu(II)and Ni(II) complexes, spectral and fluorescent properties, DFT method, geometric structure

参考

Mshchenko T.A., Turubanova V.D., Mitroshina E.V. et al. // Biophotonics. 2020. V. 13. P. e201960077. https://doi.org/10.1002/jbio.201960077
Katoh K., Yoshida Y., Yamashita M. et al. // J. Am. Chem. Soc. 2009. V. 131. № 29. P. 9967. https://doi.org/10.1021/ja902349t
Trivedi E.R., Blumenfeld C.M., Wielgos T. et al. // Tetrahedron Lett. 2016. V. 53. № 41. P. 5475. https://doi.org/10.1016/j.tetlet.2012.07.087
Chen L., Zhanga Z., Wang Y. et al. // J. Mol. Catal. 2013. V. 372. P. 114. https://doi.org/10.1016/j.molcata.2013.02.013
Goslinski T., Tykarska E., Kryjewski M. et al. // Anal. Sci. 2011. V. 27. P. 511. https://doi.org/10.2116/analsci.27.511
Saka E.T., Çağlar Y. // Catal. Lett. 2017. V. 147. P. 1471. https://doi.org/10.1007/s10562-017-2054-0
Yadav K.K., Narang U., Sahu P.K. et al. // J. Iran. Chem. Soc. 2022. V. 19. P. 4359. https://doi.org/10.1007/s13738-022-02609-5
Uranga J., Matxain J.M., Lopez X. et al. // Phys. Chem. Chem. Phys. 2017. V. 19. № 31. P. 20533. https://doi.org/10.1039/C7CP03319B
Аскаров К.А., Березин Б.Д., Быстрицкая Е.В. Порфирины: спектроскопия, электрохимия, применение. М.: Наука, 1987. 384 с.
Engeser M., Fabbrizzi L., Licchelli M. et al. // Chem. Commun. 1999. P. 1191. https://doi.org/10.1039/A901931F
Lupton J.M. // Appl. Phys. Lett. 2008. V. 81. № 13. P. 2478. https://doi.org/10.1063/1.1509115
Mamardashvili N.Zh., Koifman O.I. // Russ. J. Org. Chem. 2005. V. 41. № 6. P 787. https://doi.org/10.1007/s11178-005-0247-2
Klapshina L.G., Douglas W.E., Grigoryev I.S. et al. // J. Mater. Chem. 2009. V. 19. № 22. P. 3668. https://doi.org/10.1039/B821667C
Lermontova S.A., Grigoryev I.S., Shilyagina N.Y. et al. // Russ. J. Phys. Chem. 2016. V. 86. P. 1330. https://doi.org/10.1134/S1070363216060189
Stuzhin P.A., Goryachev M.Y., Ivanova S.S. et al. // J. Porphyr. Phthalocyanines. 2013. V. 17. № 08n09. P. 905. https://doi.org/10.1142/S1088424613500892
Chumakov D.E., Khoroshutin A.V., Anisimov A.V. et al. // Chem. Heterocycl. Compd. 2009. V. 45. № 3. P. 259. https://doi.org/10.1007/s10593-009-0277-8
Linstead R.P., Weiss P.T. // J. Chem. Soc. 1950. V. 11. P. 2975. https://doi.org/10.1039/JR9500002975
Chizhova N.V. Romanova A.O. // Rus J. Inorg. Chem. 2007. V. 52. № 11. P. 1713. https://doi.org/10.1134/S0036023607110137
Cook A.H., Linstead R.P. // J. Chem. Soc. 1937. P. 929. https://doi.org/10.1039/JR9370000929
Звездина С.В., Мальцева О.В., Чижова Н.В. и др. // Макрогетероциклы. 2014. Т. 7. № 3. С. 276. https://doi.org/10.6060/mhc140492m
Chizhova N.V., Ivanova Y.B., Rusanov A.I. et al. // Russ. J. Org. Chem. 2019. V. 55. P. 655. https://doi.org/10.1134/S1070428019050129
Lebedeva I.A., Ivanova S.S., Novakova V. et al. // J. Fluorine Chem. 2018. V. 214. P. 86. https://doi.org/10.1016/j.jfluchem.2018.08.006
Rusanov A.I., Chizhova N.V., Mamardashvili N.Zh. // Molecules. 2022. V. 27. № 23. P. 8619. https://doi.org/10.3390/molecules27238619
Lee N., Petrenko T., Bergmann U. et al. // J. Am. Chem. Soc. 2010. V. 132. № 28. P. 9715. https://doi.org/10.1021/ja101281e
Becke A.D. // Phys. Rev. A: Gen. Phys. 1988. V. 38. № 6. P. 3098. https://doi.org/10.1103/PhysRevA.38.3098
Cramer C.J. Essentials of computational chemistry: Theories and models. John Wiley & Sons, 2017. 596 p.
Moran D., Simmonett A.C., Leach F.E. et al. // J. Am. Chem. Soc. 2006. V. 128. № 29. P. 9342. https://doi.org/10.1021/ja0630285
Dunning Jr T.H., Hay P.J. Modern Theoretical Chemistry. N.Y.: Plenum, 1977. V. 3. 28 p.
Lakowicz J.R. Principles of fluorescence spectroscopy. N.Y.: Springer, 2006. V. 26. 954 p. https://doi.org/10.6060/mhc224315m
Хембрайт П. // Успехи химии. 1977. Т. 46. № 7. С. 1207. https://doi.org/10.1070/RC1977v046n07ABEH002160
Звездина С.В., Чижова Н.В., Мамардашвили Н.Ж. и др. // Макрогетероциклы. 2022. Т. 15. № 2. С. 101.
Maitarad P., Namuangruk S., Zhang D. et al. // Environ. Sci. Technol. 2014. V. 48. № 12. P. 7101. https://doi.org/10.1021/es405767d
Fukui K., Yonezawa T., Shingu H. // J. Chem. Phys. 1952. V. 20. P. 722. https://doi.org/10.1063/1.1700523
Berberan-Santos M.N. // PhysChemComm. 2000. V. 3. P. 18. https://doi.org/10.1039/b002307h
Solov'ev K.N., Borisevich E.A. // Phys.-Usp. 2005. V. 48. P. 231. https://doi.org/10.1070/PU2005v048n03ABEH001761
Drzewiecka-Matuszek A., Skalna A., Karocki A. et al. // J. Biol. Inorg. Chem. 2005. V. 10. P. 453. https://doi.org/10.1007/s00775-005-0652-6
Rubio N., Prat F., Bou N. et al. // New J. Chem. 2005. V. 29. P. 378. https://doi.org/10.1039/B415314F