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Synthesis and Acid–Base, Absorption, and Fluorescence Properties of Phthalocyanine Derivatives

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Abstract

Tetrakis{5,6-bis(4-tert-butylphenyl)pyrazino[2,3-c]}porphyrazine and tetra(4-tert-butyl)phthalocyanine have been synthesized, and their acid–base properties and electronic absorption and fluorescence spectra in acetonitrile and toluene at 298 and 295 K, respectively, have been studied. The synthesized compounds have been identified by electronic absorption and1H NMR spectroscopy and mass spectrometry. The effect of substituents in the molecular fragments of the macrocycle on the electronic and optical properties of the synthesized compounds has been estimated.

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REFERENCES

  1. Berezin, B.D., Koordinatsionnye soedineniya porfirinov i ftalotsianina (Coordination Compounds of Porphyrins and Phthalocyanine), Moscow: Nauka, 1978.

  2. Stepanov, B.I., Vvedenie v khimiyu i tekhnologiyu organicheskikh krasitelei (Introduction to the Chemistry and Technology of Organic Dyes), Moscow: Khimiya, 1984.

  3. Porfiriny: spektroskopiya, elektrokhimiya, primenenie (Porphyrins: Spectroscopy, Electrochemistry, and Application), Enikolopyan, N.S., Ed., Moscow: Nauka, 1987.

  4. Stillman, M.J. and Nyokong, T., Phthalocyanines: Properties and Applications, Leznoff, C.C. and Lever, A.B.P., Eds., New York: VCH, 1989, vol. 1, p. 133.

  5. Liu, Z., Zhang, X., Zhang, Y., and Jiang, J., Spectrochim. Acta, Part A, 2007, vol. 67, no. 5, p. 1232. https://doi.org/10.1016/j.saa.2006.10.013

    Article  CAS  Google Scholar 

  6. Nonlinear Optics of Organic Molecules and Polymers, Nalwa, H.S. and Miyata, S., Eds., Boca Raton: CRC, 1997.

  7. Sheinin, V.B. and Ivanova, Yu.B., Russ. J. Phys. Chem. A, 2007, vol. 81, no. 8, p. 1250. https://doi.org/10.1134/S0036024407080134

    Article  CAS  Google Scholar 

  8. Petrov, O.A., Osipova, G.V., and Khelevina, O.G., Macroheterocycles, 2009, vol. 2, no. 2, p. 151.

    Article  CAS  Google Scholar 

  9. Bershtein, I.Ya. and Kaminskii, Yu.L., Spektrofotometricheskii analiz v organicheskoi khimii (Spectrophotometric Analysis in Organic Chemistry), Leningrad: Khimiya, 1986.

  10. Andrianov, V.G. and Malkova, O.V., Macroheterocycles, 2009, vol. 2, no. 2, p. 130.

    Article  CAS  Google Scholar 

  11. Hirao, H., J. Phys. Chem. A, 2011, vol. 115, no. 33, p. 9308. https://doi.org/10.1021/jp2052807

    Article  CAS  PubMed  Google Scholar 

  12. Dhami, S., Mello, A.D., Rumbles, G., Bishop, S.M., Phillips, D., and Beeby, A., Photochem. Photobiol., 1995, vol. 61, no. 4, p. 341. https://doi.org/10.1111/j.1751-1097.1995.tb08619.x

    Article  CAS  Google Scholar 

  13. Whalley, M., J. Chem. Soc., 1961, p. 866. https://doi.org/10.1039/JR9610000866

  14. Lakowicz, J.R., Principles of Fluorescence Spectroscopy, New York: Springer, 2006, 3rd ed.

  15. Freyer, W., Mueller, S., and Teuchner, K.J., J. Photochem. Photobiol., C, 2004, vol. 163, nos. 1–2, p. 231. https://doi.org/10.1016/j.jphotochem.2003.12.003

    Article  CAS  Google Scholar 

  16. Vachova, L., Novakova, V., Kopecky, K., Miletin, M., and Zimcik, P., Dalton Trans., 2012, vol. 41, no. 38, p. 11651. https://doi.org/10.1039/c2dt31403g

    Article  CAS  PubMed  Google Scholar 

  17. Karyakin, Yu.V. and Angelov, I.I., Chistye khimicheskie reaktivy (Pure Chemicals), Moscow: Khimiya, 1974, 4th ed.

  18. Ivanova, Yu.B., Churakhina, Yu.I., and Mamardashvili, N.Zh.,Russ. J. Gen. Chem., 2008, vol. 78, no. 4, p. 673. https://doi.org/10.1134/S1070363208100265

    Article  CAS  Google Scholar 

  19. Ivanova, Yu.B., Sheinin, V.B., and Mamardashvili, N.Zh., Russ. J. Gen. Chem., 2007, vol. 77, no. 8, p. 1458. https://doi.org/10.1134/S1070363207080270

    Article  CAS  Google Scholar 

  20. Ivanova, Yu.B. and Mamardashvili, N.Zh., J. Fluoresc., 2017, vol. 27, no. 5, p. 303. https://doi.org/10.1007/s10895-016-1958-1

    Article  CAS  PubMed  Google Scholar 

  21. Ivanova, Yu.B., Mamardashvili, N.Zh., Semeikin, A.S., and Glazunov, A.V., Russ. J. Org. Chem., 2010, vol. 46, no. 6, p. 917. https://doi.org/10.1134/S1070428010060230

    Article  CAS  Google Scholar 

  22. Kruk, N.N., Starukhin, A.S., Mamardashvili, N.Zh., Sheinin, V.B., and Ivanova, Yu.B., RU Patent no. 2345352, 2009.

  23. Ivanova, Yu.B., Chizhova, N.V., Pukhovskaya, S.G., and Mamardashvili, N.Zh., Russ. J. Gen. Chem., 2014, vol. 84, no. 5, p. 939. https://doi.org/10.1134/S1070363214050260

    Article  CAS  Google Scholar 

  24. Nguyen, N.T., Mamardashvili, G.M., Kulikova, O.M., Scheblykin, I.G., Mamardashvili, N.Z., and Dehaen, W., RSC Adv., 2014, vol. 4, no. 38, p. 19703. https://doi.org/10.1039/C3RA45660A

    Article  Google Scholar 

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Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-73-20079) using the facilities of the Upper Volga Regional Center for Physicochemical Studies.

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Authors and Affiliations

  1. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045, Ivanovo, Russia

    Yu. B. Ivanova, O. A. Dmitrieva, T. V. Lyubimova & N. Zh. Mamardashvili

  2. Ivanovo State University of Chemistry and Technology, 153460, Ivanovo, Russia

    Yu. V. Khrushkova, T. V. Lyubimova & A. S. Semeikin

Authors
  1. Yu. B. Ivanova
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  2. O. A. Dmitrieva
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  3. Yu. V. Khrushkova
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  4. T. V. Lyubimova
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  5. A. S. Semeikin
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  6. N. Zh. Mamardashvili
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Correspondence to Yu. B. Ivanova.

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Ivanova, Y.B., Dmitrieva, O.A., Khrushkova, Y.V. et al. Synthesis and Acid–Base, Absorption, and Fluorescence Properties of Phthalocyanine Derivatives. Russ J Gen Chem 90, 852–857 (2020). https://doi.org/10.1134/S1070363220050151

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  • DOI: https://doi.org/10.1134/S1070363220050151

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