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Synthesis and study of immobilized porphyrins on the basis of acrylic polymer carriers

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Abstract

In order to obtain porphyrin-containing polymers, the copolymerization of acrylate monomers of the various structures with natural porphyrin, namely methyl pheophorbide a (MPP) and its complex with copper (CuMPP) in tetrahydrofuran and toluene was studied. The copolymers of methyl methacrylate (MMA) with MPP or CuMPP, glycidyl methacrylate (GMA) with MPP or CuMPP having different compositions were synthesized. The influence of the nature of the solvent, the initial mass ratio of the monomers during copolymerization on the structure, composition, and properties of the obtained compounds were investigated. The study of the physico-chemical, molecular weight, structural, and chemical characteristics of the prepared copolymers was carried out. The possibility of controlled synthesis of the copolymers with controlled molecular weight characteristics by varying the parameters of the reaction medium was shown.

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References

  1. O. I. Koifman, T. A. Ageeva, Porphirinpolimery:sintez, svoystva, primenenie [Polymers: Synthesis, Properties, Applications], LENAND, Moscow, 2018, 304 p. (in Russian).

    Google Scholar 

  2. O. I. Koifman, T. A. Ageeva, Polym. Sci., Ser. C. (Engl. Transl.), 2004, 46, 49.

    Google Scholar 

  3. O. I. Nikolaeva, T. A. Ageeva, O. I. Koifman, Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. (Engl. Transl.), 2004, 91.

  4. O. I. Koifman, T. A. Ageeva, M. I. Bazanov, D. B. Berezin, Funktsional’nye materialy na osnove tetrapirol’nikh makrogeterotsiklicheskikh soedineniy [Functional Materials Based on Tetrapyrrole Macroheterocyclic Compounds], LENAND, Moscow, 2019, 848 p. (in Russian).

    Google Scholar 

  5. O. I. Koifman, T. A. Ageeva, I. P. Beletskaya, A. D. Averin, A. A. Yakushev, L. G. Tomilova, T. V. Dubinina, A. Y. Tsivadze, Y. G. Gorbunova, A. G. Martynov, D. V. Konarev, S. S. Khasanov, R. N. Lyubovskaya, T. N. Lomova, V. V. Korolev, E. I. Zenkevich, T. Blaudeck, C. von Borczyskowski, D. R. T. Zahn, A. F. Mironov, N. A. Bragina, A. V. Ezhov, K. A. Zhdanova, P. A. Stuzhin, G. L. Pakhomov, N. V. Rusakova, N. N. Semenishyn, S. S. Smola, V. I. Parfenyuk, A. S. Vashurin, S. V. Makarov, I. A. Dereven’kov, N. Z. Mamardashvili, T. S. Kurtikyan, G. G. Martirosyan, V. A. Burmistrov, V. V. Aleksandriiskii, I. V. Novikov, D. A. Pritmov, M. A. Grin, N. V. Suvorov, A. A. Tsygankov, A. Y. Fedorov, N. S. Kuzmina, A. V. Nyuchev, V. F. Otvagin, A. V. Kustov, D. V. Belykh, D. B. Berezin, A. B. Solovieva, P. S. Timashev, E. R. Milaeva, Y. A. Gracheva, M. A. Dodokhova, A. V. Safronenko, D. B. Shpakovsky, S. A. Syrbu, Y. A. Gubarev, A. N. Kiselev, M. O. Koifman, N. S. Lebedeva, E. S. Yurina, Macroheterocycles (Engl. Transl.), 2020, 13, 311; DOI: https://doi.org/10.6060/mhc200814k.

    Article  Google Scholar 

  6. T. A. Ageeva, S. A. Syrbu, O. I. Koifman, Macroheterocycles (Engl. Transl.), 2009, 2, 139; DOI: https://doi.org/10.6060/mhc2009.2.139.

    Article  CAS  Google Scholar 

  7. O. I. Nikolaeva, Y. V. Romanenko, T. A. Ageeva, O. I. Koifman, Macroheterocycles (Engl. Transl.), 2012, 5, 139; DOI: https://doi.org/10.6060/mhc2012.120679n.

    Article  Google Scholar 

  8. O. I. Nikolaeva, T. A. Ageeva, S. T. Rashidova, M. E. Glazkova, O. I. Koifman, Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol., 2010, 64 (in Russian).

  9. Polimernie reagenti i katalizatory [Polimeric Reagents and Catclysts], Ed. W. E. Ford, Khimiya, Moscow, 1991, 256 p. (in Russian).

    Google Scholar 

  10. A. Gyot, M. Negre, M. Bartolin, Progr. Polym. Sci., 1982, 18, 14.

    Google Scholar 

  11. M. A. Korshunov, V. S. Mikhlin, Glitsidilmetakrilat. Khimicheskaya entsiklopediya [Glycidyl methacrylate. Chemical Encyclopedia], Soviet Encyclopedia, Moscow, 1988, 1147 p. (in Russian).

    Google Scholar 

  12. M. A. Korshunov, B. C. Mikhlin, S. V. Marusina, O. B. Potopchina, Sintez i primenenie glitsidilmetakrilata. Tematicheskiy obzor [Synthesis and Application of Glicydyl Methacrylate. A Thematic Review], Tsentral’nyi Nauchno-Issledovatel’skii Institut Informatsii i Tekhniko-Ekonomicheskikh Issledovanii Neftepererabatyvayushchei i Neftekhimicheskoi Prom-ti, Moscow, 1979, 60 p. (in Russian).

  13. V. F. Kurenkov, L. A. Budarina, A. E. Zaikin, Praktikum po khimii i fizike visokomolekulyarnikh soedineniy [Laboratory works in Chemistry and Physics of High-Molecular-weight Compounds], Kolos S, Moscow, 2008, 395 p. (in Russian).

    Google Scholar 

  14. Entsiklopediya polimerov [Encyclopedia of Polymers], Soviet Encyclopedia, Moscow, 1972, 1224 p. (in Russian).

  15. Porphyrins and Metalloporphyrins, Ed. K. M. Smith, Elsevier, Amsterdam, 1975, 890 p.

    Google Scholar 

  16. T. N. Lomova, Aksial’no koordinirovannye metalloporphirini vnauke Ipraktike [Axially Coordinated Metalloporphyrins in Science and Practice], KRASAND, Moscow, 2018, 700 p. (in Russian).

    Google Scholar 

  17. A. Gordon, R. Ford, Sputnik Khimii [The Chemist’s Companion], Mir, Moscow, 1972, 541 p. (in Russian).

    Google Scholar 

  18. A. Weissberger, E. Proskauer, J. Riddick, E. Toops, Organicheskie rastvoriteli. Fizicheskie svoistva I metodi ochistki [Organic Solvents: Physical Properties and Methods of Purification], Foreign Languages Publishing House, Moscow, 1958, 520 p. (in Russian).

    Google Scholar 

  19. L. Jaquinod, in The Porphyrin Handbook, Eds K. M. Kadish, K. M. Smith, R. Guilard, 2000, 201 p.

  20. O. I. Koifman, G. E. Nikitina, B. D. Berezin, Russ. J. Phys. Chem. (Engl. Transl.), 1982, 737.

  21. O. I. Koifman, G. E. Nikitina, B. D. Berezin, Russ. J. Phys. Chem. (Engl. Transl.), 1982, 590.

  22. A. S. Semeykin, O. I. Koifman, G.E. Nikitina, Gen. Chem. USSR (Engl. Transl.), 1984, 1599.

  23. M. E. Glazkova, T. A. Ageeva, O. I. Nikolaeva, Yu. V. Rumyantseva, O. I. Koifman, Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol., 2011, 104.

  24. S. V. Kurmaz, E. O. Perepelitsina, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 835.

    Article  CAS  Google Scholar 

  25. Yu. B. Monakov, O. I. Koifman, T. A. Ageeva, R. M. Islamova, R. N. Nasretdinova, Uspekhi Khimii Porfirinov [Advances in Porphyrin Chemistry], Ed. O. A. Golubchikov, Vol. 5, NII Khimii SPbGU, St. Petersburg, 2001, 293 p. (in Russian).

  26. R. M. Islamova, S. V. Nazarova, O. I. Koifman, Macro-heterocycles, 2011, 4, 97; DOI: https://doi.org/10.6060/mhc2011.2.06.

    CAS  Google Scholar 

  27. V. F. Razumov, A. G. Ivanchenko. A. D. Pomogaylo, I. S. Voloshanovsky, A. I. Kuzaev, Polym. Sci., Ser. B (Engl. Transl.), 1997, 2046.

  28. A. D. Pomogailo, V. F. Razumov, I. S. Voloshanovskii, J. Porphyrins Phthalocyanines, 2000, 4, 45.

    Article  CAS  Google Scholar 

  29. O. I. Nikolaeva, T. A. Ageeva, O. I. Koifman, Russ. Chem. J., 2017, 60.

  30. O. I. Nikolaeva, T. A. Ageeva, O. I. Koifman, J. Porphyrins Phthalocyanines, 2008, 12, 437.

    Google Scholar 

  31. D. B. Berezin, Makrotsiklichesky effect I strukturnaya khimiya porfirinov [Macrocyclic Effect and Structural Chemistry of Porphyrins], KRASAND, Moscow, 2010, 424 p. (in Russian).

    Google Scholar 

  32. B. D. Berezin, D. B. Berezin, Khromophornye sistemy makritsiklov I lineynikh molekul [Chromophore Systems of Macrocycles and Linear Molecules], KRASAND, Moscow, 2013, 240 p. (in Russian).

    Google Scholar 

  33. A. H. Kuptsov G. N. Zhizhin, Fourier-KR i Fourier-IK spektry polimerov [Fourier Transform Raman and IR spectra of polymers], Technosphere, Moscow, 2013, 696 p. (in Russian).

    Google Scholar 

  34. M. I. Shtilman, Polimery medico-biologicheskogo naznacheniya: uchebnoe posobie [Polymers of Medical and Biological Purpose: a Textbook for Universities], Akademkniga, Moscow, 2006, 400 p. (in Russian).

    Google Scholar 

  35. I. A. Nikolaeva, J. V. Morozova, M. G. Zavialova, R. A. Novikov, Ya. V. Tkachev, V. P. Timofeev, A. Yu. Misharin, G. V. Ponomarev, Macroheterocycles, 2010, 3, 150.

    Article  CAS  Google Scholar 

  36. M. B. Berezin, Termokhimiya solvatatsii khlorofilla i rodstvennykh soedineniy [Thermochemistry of Chlorophyll Solvation and Related Compounds], KRASAND, MOSCOW, 2008, 256 p. (in Russian).

  37. A. A. Tager, Fiziko-khimiya polimerov [Physical Chemistry of Polymers], Nauchniy Mir, Moscow, 2007, 575 p. (in Russian).

    Google Scholar 

  38. V. V. Arslanov, M. A. Kalinina, E. V. Ermakova, O. A. Raitman, Yu. G. Gorbunova, O. E. Aksyutin, A. G. Ishkov, V. A. Grachev, A. Yu. Tsivadze, Russ. Chem. Rev., 2019, 88, 775.

    Article  CAS  Google Scholar 

  39. M. P. Faustova, E. D. Nikolskaya, M. D. Mollaev, M. B. Sokol, A. I. Zabolotskiy, O. A. Zhunina, M. V. Fomicheva, V. I. Shvets, A. V. Lobanov, N. G. Yabbarov, Russ. Chem. Bull. (Int. Ed.), 68, 2216.

  40. O. I. Koifman, T. A. Ageeva, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 2001.

    Article  CAS  Google Scholar 

  41. D. A. Pomogaylo, I. E. Uflyand, Makromolekulyarnye metallokhelaty [Macromolecular Metal Chelates], Khimiya, Moscow, 1991, 304 p. (in Russian).

    Google Scholar 

  42. A. B. Solov’eva, S. F. Timashev Uspekhi Khimii Porfirinov [Advances in Porphyrin Chemistry], NII Khimii SPbGU, St. Petersburg, 2003, 1081 (in Russian).

    Google Scholar 

  43. T. Mathew, M. Padmanabhan, S. Kuriakose, J. Appl. Polym. Sci., 1996, 59, 23.

    Article  CAS  Google Scholar 

  44. M. Sanchez, N. Chap, J.-B. Cazaux, B. Meunier, Eur. J. Inorg. Chem., 2001, 1775.

  45. M. A. Valles, Uspekhi Khimii Porfirinov [Advances in Porphyrin Chemistry], Vol. 3, NII Khimii SPbGU, St. Petersburg, 2001, 179 p. (in Russian).

    Google Scholar 

  46. Yu. S. Tarkhanovskiy, Intelektual’nie lipidnye nanokonteynery d adresnoy dostavke d lekarstvennykh veshestv [Smart Lipid-like Nanocages for targeted drug delivery], LKI, Moscow, 2011, 280 p. (in Russian).

    Google Scholar 

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Correspondence to O. I. Nikolaeva.

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Based on the materials of the VIII All-Russian Kargin Conference “Polymers-2020” (November 9–13, 2020, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1822–1831, September, 2021.

The work was carried out within the framework of the state task of the Ministry of Science and Higher Education of the Russian Federation (Project No. FZZW-2020-0008).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Nikolaeva, O.I., Ageeva, T.A. & Koifman, O.I. Synthesis and study of immobilized porphyrins on the basis of acrylic polymer carriers. Russ Chem Bull 70, 1822–1831 (2021). https://doi.org/10.1007/s11172-021-3288-y

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  • DOI: https://doi.org/10.1007/s11172-021-3288-y

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