Abstract
The kinetics of complex formation between zinc and 5,10,15,20-tetraphenylporphyrin and 5,10,15,20-tetra(4-hydroxyphenyl)porphyrin in acetonitrile is studied in the temperature range from 298 to 318 K. The fluorescent properties of these compounds are examined, the emission in the red region of the spectrum is measured, and the fluorescence quantum yields are determined. It is found that although the electronic absorption spectra of the studied compounds are almost identical, hydroxyl substituents are observed to have a considerable effect on the chelating ability of ligands. The rate constant of the formation of ZnT(4-OH-Ph)P is thus approximately three times higher than that of ZnTPhP, with the energy consumption being lower (about 20 kJ mol–1). The calculated fluorescence quantum yields of H2TPhP, H2T(4-OH-Ph) P, ZnTPhP, and ZnT(4-OH-Ph)P in acetonitrile are half those in toluene, while the ratio between the quantum yields of ligands and their metal complexes is a constant equal to approximately 3 and does not depend on which solvent is used.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
B. D. Berezin, Coordination Compounds of Porphyrins and Phthalocyanines (Wiley, New York, 1981).
Yu. B. Ivanova, Dao Tkhe Nam, A. V. Glazunov, A. S. Semeikin, and N. Zh. Mamardashvili, Russ. J. Gen. Chem. 82, 1272 (2012).
Yu. B. Ivanova, T. N. Dao, N. N. Kruk, and S. A. Syrbu, Russ. J. Gen. Chem. 83, 1155 (2013).
B. D. Berezin, in Achievements of Porphyrine Chemistry, Ed. by O. A. Golubchikov (NII Khim. SPbGU, St. Petersburg, 1997), Vol. 1, p. 94 [in Russian].
F. R. Longo, M. G. Finarelly, and J. B. Kim, J. Heterocycl. Chem. 6, 927 (1969).
A. S. Semeikin, O. I. Koifman, and B. D. Berezin, Chem. Heterocycl. Compd. 18, 1046 (1982).
A. S. Semeikin, O. I. Koifman, B. D. Berezin, et al., Chem. Heterocycl. Compd. 19, 1082 (1983).
Yu. V. Karyakin and I. I. Angelov, Pure Chemical Reagents (Khimiya, Moscow, 1974) [in Russian].
D. Barton and W. D. Ollis, Comprehensive Organic Chemisty (Pergamon, Oxford, UK, 1979; Nauka, Moscow, 1985).
Yu. B. Ivanova, N. V. Chizhova, and N. N. Kruk, Russ. J. Gen. Chem. 83, 558 (2013).
B. D. Berezin and O. G. Khelevina, Porphyrins: Structure, Properties, and Synthesis (Nauka, Moscow, 1985) [in Russian].
N. S. Dudkina, P. A. Shatunov, E. M. Kuvshinova, S. G. Pukhovskaya, A. S. Semeikin, and O. A. Golubchikov, Russ. J. Gen. Chem. 68, 1955 (1998).
O. A. Golubchikov, S. G. Pukhovskaya, and E. M. Kuvshinova, Russ. Chem. Rev. 74, 249 (2005).
Yu. B. Ivanova, O. V. Razgonyaev, A. S. Semeikin, and N. Zh. Mamardashvili, Russ. J. Phys. Chem. A 90, 994 (2016).
J. P. Strachan, S. Gentemann, J. Seth, et al., J. Am. Chem. Soc. 119, 11191 (1997).
L. V. Levshin and A. M. Saletskii, Luminescence and Its Measurement (Mosk. Gos. Univ., Moscow, 1989) [in Russian].
J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd ed. (Univ. of Maryland School of Medicine Baltimore, Springer, Maryland, USA, 2010).
I. K. Shushkevich, P. P. Pershushkevich, A. P. Stupak, and K. N. Solov’ev, J. Appl. Spectrosc. 72, 767 (2005).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © Yu.B. Ivanova, A.S. Parfenov, N.Zh. Mamardashvili, 2017, published in Zhurnal Fizicheskoi Khimii, 2017, Vol. 91, No. 1, pp. 93–98.
Rights and permissions
About this article
Cite this article
Ivanova, Y.B., Parfenov, A.S. & Mamardashvili, N.Z. Chelation and fluorescence properties of tetraphenylporphyrin and 5,10,15,20-tetra(4-hydroxyphenyl)porphyrin in acetonitrile. Russ. J. Phys. Chem. 91, 94–99 (2017). https://doi.org/10.1134/S0036024416120153
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024416120153