Skip to main content
SpringerLink
Log in

Spectrophotometric Study of Acid-Base Properties of Sulfonated Derivatives of 5,10,15,20-Tetraphenyl-21-thiaand 5,10,15,20-Tetraphenyl-21-oxoporphyrins in the Ethanol–Sulfuric Acid System

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Spectral and basic properties of heterosubstituted porphyrins of anionic type have studied by means of spectrophotometric titration in comparison with their structural analog — tetraphenylporphine tetrasulfonic acid. The parameters of electronic absorption spectra and concentration ranges of existence of the mono- and diprotonated forms of the studied ligands as well as the constants of basic dissociation have been determined. Comparative analysis of the effect of the reactive site modification and the medium composition on the basicity of the compounds has been performed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Kadish, K.M., Smith, K.M., and Guilard, R., The Porphyrin Handbook, San Diego: Academic Press, 2000, vol. 3, p. 364.

    Google Scholar 

  2. Kadish, K.M., Smith, K.M., and Guilard, R., The Porphyrin Handbook, New York: Academic Press, 2000, vol. 2, p. 361.

    Google Scholar 

  3. Ambre, R.,. Yu, C.-Y, Mane, S., B., Yao, C.-F., and Hung, C.-H., Tetrahedron, 2011, vol. 67, no. 25, p. 4680. doi 10.1016/j.tet.2011.04.034

    Article  CAS  Google Scholar 

  4. Broadhurst, M.J., Grigg, R., and Johnson, A.W., J. Chem. Soc. (D), 1969, vol. 24, p. 1449. doi 10.1039/C29690001480

    Google Scholar 

  5. Broadhurst, M.J., Grigg, R.,and Johnson, A.W., J. Chem. Soc. (D), 1970, p. 807. doi 10.1039/C29700000807

    Google Scholar 

  6. Broadhurst, M.J. and Grigg, R., J. Chem. Soc. (C), 1971, p. 3681. doi 10.1039/J3971000368.1

    Google Scholar 

  7. Chmielewski, P.J. and Latos-Grażyński, L., Inorg. Chem., 1998, vol. 37, p. 4179. doi 10.1021/ic971387i

    Article  CAS  PubMed  Google Scholar 

  8. Sridevi, B., Narayanan, S.J., Srinivasan, A., Chandrashekar, T.K., and Subramanian, J., J. Chem. Soc. Dalton Trans., 1998, p. 1979. doi 10.1039/A801934G

    Google Scholar 

  9. Chmielewski, L., Latos-Grażyński, L., Olmstead, M.M., and Balch, A.L., Chem. Eur. J., 1997, vol. 3, no. 2, p. 268. doi 10.1002/chem.19970030216

    Article  CAS  PubMed  Google Scholar 

  10. Latos-Grażyński, L., Pacholska, E., Chmielewski, P.J., Olmstead, M.M., and Balch, A.L., Inorg. Chem., 1996, vol. 35, p. 566. doi 10.1021/ic950329z

    Article  Google Scholar 

  11. Chatterjee, T., Shetti, V.S., Sharma, R., and Ravikanth, M., Chem. Rev., 2017, vol. 117, no. 4, p. 3254. doi 10.1021/acs.chemrev.6b00496

    Article  CAS  PubMed  Google Scholar 

  12. Lash, T.D. and Ferrence, G.M., Inorg. Chem., 2017, vol. 56, no. 18, p. 11426. doi 10.1021/acs.inorgchem.7b01946

    Article  CAS  PubMed  Google Scholar 

  13. Chmielewski, P.J., Pawlicki, M., Sprutta, N., Szterenberg, L., and Latos-Grażyński, L., Inorg. Chem., 2006, vol. 45, no. 21, p. 8664. doi 10.1021/ic061091p

    Article  CAS  PubMed  Google Scholar 

  14. Tagawa, K., Mori, S., Okujima, T., Takase, M., and Uno, H., Tetrahedron, 2017, vol. 73, p. 794. doi 10.1016/j.tet.2016.12.067

    Article  CAS  Google Scholar 

  15. Stilts, C.E., Nelen, M.I., Hilmey, D.G., Davies, S.R., Gollnick, S.O., Oseroff, A.R., Gibson, S.L., Hiff, R., and Detty, M.R., J. Med. Chem., 2000, vol. 43, p. 2403. doi 10.1021/jm000044i

    Article  CAS  PubMed  Google Scholar 

  16. Hilmey, D.G., Abe, M., Nelen, M.I., Stilts, C.E., Baker, G.A., Baker, S.N., Bright, F.V., Davies, S.R., Gollnick, S.O., Oseroff, A.R., Gibson, S.L., Hilf, R., and Detty, M.R., J. Med. Chem., 2002, vol. 45, p. 449. doi 10.1021/jm0103662

    Article  CAS  PubMed  Google Scholar 

  17. You, Y., Gibson, S.L., Hilf, R., Davies, S.R., Oseroff, A.R., Roy, I., Ohulchanskyy, T.Y., Bergey, E.J., and Detty, M.R., J. Med. Chem., 2003, vol. 46, p. 3734. doi 10.1021/jm030136i

    Article  CAS  PubMed  Google Scholar 

  18. O’Connor, A.E., Gallagher, W.M., and Byrne, A.T., Photochem. Photobiol., 2009, vol. 85, no. 5. P 1053. doi 10.1111/j.1751-1097.2009.00585.x

  19. Marydash, B. and Madhuri, B., J. Med. Chem., 2018, vol. 61, no. 11, p. 5009. doi 10.1021/acs.jmedchem.8b00460

    Article  CAS  Google Scholar 

  20. Cassidy, C.M., Tunney, M.M., McCarron, P.A., and Donnelly, R.F., J. Photochem. Photobiol. (B), 2009, vol. 95, no. 2, p. 71. doi 10.1016/j.jphotobiol.2009.01.005

    Article  CAS  Google Scholar 

  21. Dickinson, T.A., White, J., Kauer, J.S., and Walt, D.R., Nature, 1996, vol. 382, p. 697. doi 10.1038/382697a0

    Article  CAS  PubMed  Google Scholar 

  22. Ethirajan, M., Chen, Y., Joshi, P., and Pandey, R.K., Chem. Soc. Rev., 2011, vol. 40, p. 340. doi 10.1039/B915149B

    Article  CAS  PubMed  Google Scholar 

  23. Andrianov, V.G. and Malkova, O.V., Macroheterocycles, 2009, vol. 2, p. 130.

    Article  CAS  Google Scholar 

  24. Fialkov, Yu.Ya., Rastvoritel’ kak sredstvo upravleniya khimicheskim protsessom (Solvent As a Chemical Process Management Tool), Leningrad: Khimiya, 1990, p. 240.

    Google Scholar 

  25. Knyukshto, V.N., Starukhin, A.S., Kruk, M.M., and Gorskii, A.V., J. Appl. Spectr., 2018, vol. 84, no. 6. doi 10.1007/10812-018-0571-2

  26. Dolman, D. and Stewart, R., Can. J. Chem., 1967, vol. 45, p. 903. doi 10.1139/v67-156

    Article  CAS  Google Scholar 

  27. Sheinin, V.B., Shabunin, S.A., Bobritskaya, E.V., Ageeva, T.A., and Koifman, O.I., Macroheterocycles, 2012, vol. 5, no. 3, p. 252. doi 10.6060/mhc2012.120989s

    Article  CAS  Google Scholar 

  28. Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Organic Solvents: Physical Properties and Methods of Purification, New York: Interscience Publishers, 1955.

    Google Scholar 

  29. Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley, 1972.

    Google Scholar 

  30. Pukhovskaya, S., Ivanova, Yu., Nama, D.T., and Vashurin, A., J. Porph. Phthalocyan., 2015, vol. 19, p. 858. doi 10.1142/S1088424615500649

    Article  CAS  Google Scholar 

  31. Ivanova, Yu.B., Churakhina, Yu.I., and Mamardashvili, N.Zh., Russ. J. Gen. Chem. 2008, vol. 78, no. 4, p. 673. doi 10.1134/S1070363208040269

    Google Scholar 

  32. Bushy, C.A., Dinello, R.K., and Dolphin, D.A., Can. J. Chem., 1975, vol. 53, no. 11, p. 1554. doi 10.1139/v75-219

    Article  Google Scholar 

  33. Ramasany, P., Pandian, P., Tavarekere, K., and Chandrashekar, K., J. Chem. Soc. Dalton Trans., 1993, vol. 1, no. 1, p. 119. doi 10.1039/DT9930000119

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Krestov Institute of Chemistry of Solutions of the Russian Academy of Sciences, Ivanovo, Russia

    S. A. Syrbu & Yu. B. Ivanova

  2. Ivanovo State University of Chemistry and Technology, pr. Sheremetevskii 7, Ivanovo, 153000, Russia

    S. G. Pukhovskaya & A. S. Vashurin

Authors
  1. S. A. Syrbu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Pukhovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. B. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. S. Vashurin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. G. Pukhovskaya.

Additional information

Russian Text © S.A. Syrbu, S.G. Pukhovskaya, Yu.B. Ivanova, A.S. Vashurin, 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 2, pp. 258–264.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Syrbu, S.A., Pukhovskaya, S.G., Ivanova, Y.B. et al. Spectrophotometric Study of Acid-Base Properties of Sulfonated Derivatives of 5,10,15,20-Tetraphenyl-21-thiaand 5,10,15,20-Tetraphenyl-21-oxoporphyrins in the Ethanol–Sulfuric Acid System. Russ J Gen Chem 89, 255–260 (2019). https://doi.org/10.1134/S1070363219020142

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219020142

Keywords

Search

Navigation