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Non-covalent associates of metal phthalocyanines: the role of axial ligand and catalytic activity

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Abstract

The problem about the role of the coordinated exobidentate ligand in the formation of dimeric structures of sulfonated cobalt phthalocyanine derivatives is considered. The size of the peripheral substituent of the macrocycle and remoteness of the ionogenic group from the macrocycle play the key role in the formation of dimers of a specified type. As the extension of the peripheral substituent of the macrocycle increases, the stability of dimeric associates of the Н-type decreases and that of the associates formed due to the donor—acceptor interaction (J- and Т-aggregates) increases. The latter can be stabilized by hydrogen bonds at the periphery of the macromolecule. A series of catalytic activity of the macrocycles under study is inverted compared to the series of stability of the H-dimers.

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References

  1. C. Colomban, E. V. Kudrik, P. Afanasiev, A. B. Sorokin, Catalysis Today, 2014, 235, 14.

    Article  CAS  Google Scholar 

  2. J. C. Bricker, L. Laricchia, Topics Catal., 2012, 55, 1315.

    Article  CAS  Google Scholar 

  3. V. Çakir, D. Çakir, M. Pişkin, M. Durmuş, Z. Biyiklioğlu, J. Luminescence, 2014, 154, 274.

    Article  Google Scholar 

  4. A. Günsela, A. T. Bilgiçlia, E. Kirbaçb, S. Güneyc, M. Kandaza, J. Photochem. Photobiol. A: Chem., 2015, 310, 155.

    Article  Google Scholar 

  5. H.-N. Xu, H.-J. Chen, B.-Yu. Zheng, Yu.-Q. Zheng, M.-R. Ke, J.-D. Huang, Ultrasonics Sonochemistry, 2015, 22, 125.

    Article  CAS  Google Scholar 

  6. S. Mori, H. Yoshiyama, E. Tokunaga, N. Iida, M. Hayashi, T. Obata, M. Tanaka, N. Shibata, J. Fluor. Chem., 2015, 174, 137.

    Article  CAS  Google Scholar 

  7. Y. G. Gorbunova, A. G. Martynov, A. Yu. Tsivadze, in Handbook of Porphyrin Science, Eds K. M. Kadish, K. M. Smith, R. Guilard, World Scientific, 2012.

    Google Scholar 

  8. T. Basova, A. Hassan, M. Durmuş, A. G. Gürekd, V. Ahsen, Coord. Chem. Rev., 2016, 310, 131.

    Article  CAS  Google Scholar 

  9. C. J. Medforth, Zh. Wang, K. E. Martin, Yu. Song, J. L. Jacobsen, J. A. Shelnutt, Chem. Commun., 2009, 7261.

    Google Scholar 

  10. M. A. Gradova, K. A. Zhdanova, N. A. Bragina, A. V. Lobanov, M. Ya. Mel´nikov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 806 [Izv. Akad. Nauk, Ser. Khim., 2015, 806].

    Article  CAS  Google Scholar 

  11. M. Shaik, V. K. Rao, M. Gupta, P. Pandey, Thin Solid Films, 2012, 526, 256.

    Article  CAS  Google Scholar 

  12. V. B. Sheinin, E. V. Bobritskaya, S. A. Shabunin, O. I. Koifman, Macroheterocycles, 2014, 7, 209.

    Article  CAS  Google Scholar 

  13. Yu. Bandera, M. K. Burdette, J. A. Shetzline, R. Jenkins, S. E. Creager, S. H. Foulger, Dyes and Pigments, 2016, 125, 72.

    Article  CAS  Google Scholar 

  14. V. Çakir, M. Göksel, M. Durmuş, Z. Biyiklioğlu, Dyes and Pigments, 2016, 125, 414.

    Article  Google Scholar 

  15. S. Z. Yildiz, S. Colak, M. Tuna, J. Mol. Liq., 2014, 195, 22.

    Article  CAS  Google Scholar 

  16. B. D. Berezin, O. I. Koifman, Russ. Chem. Rev., 1980, 49, 1188.

    Article  Google Scholar 

  17. Yu. S. Marfin, A. S. Vashurin, E. V. Rumyantsev, S. G. Puhovskaya, J. Sol-Gel Sci. Technol., 2013, 66, 306.

    Article  CAS  Google Scholar 

  18. A. A. Voronina, I. A. Tarasyuk, Yu. S. Marfin, A. S. Vashurin, E. V. Rumyantsev, S. G. Pukhovskaya, J. Non-Crystal. Solids, 2014, 406, 5.

    Article  CAS  Google Scholar 

  19. G. P. Shaposhnikov, V. P. Kulinich, V. E. Maizlish, Modifitsirovannye ftalotsianiny i ikh strukturnye analogi [Modified Phthalocyanines and Their Structural Analogs], KRASAND, Moscow, 2012, 480 pp. (in Russian).

    Google Scholar 

  20. J-Aggregates, Ed. T. Kobayashi, World Scientific, Singapore, Vol. 2, 2012.

  21. A. W. Snow, in The Porphyrin Handbook, Eds K. M. Kadish, K. M. Smith, R. Guilard, Academic Press, New York, 2003, Vol. 17, p. 129.

    Book  Google Scholar 

  22. M. Sevim, M. N. Yarasir, A. Koca, M. Kandaz, Dyes and Pigments, 2014, 111, 190.

    Article  CAS  Google Scholar 

  23. V. Iliev, V. Alexiev, L. Bilyarska, J. Mol. Catal. A: Chem., 1999, 137, 15.

    Article  CAS  Google Scholar 

  24. M. Kobayashi, Yu. Kigawa, K. Satoh, K. Sawada, J. Porphyrins and Phthalocyanines, 2012, 16, 183.

    Article  CAS  Google Scholar 

  25. A. L. Lyubimtsev, I. E. Nifant´ev, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 346 [Izv. Akad. Nauk, Ser. Khim., 2004, 332].

    Article  CAS  Google Scholar 

  26. M. Kimura, Y. Yamaguchi, T. Koyama, K. Hanabusa, H. Shirai, J. Porphyrins and Phthalocyanines, 1997, 1, 309.

    Article  CAS  Google Scholar 

  27. A. N. Sidorov, I. P. Kotlyar, Opt. Spektrosk. [Optics and Spectroscopy], 1961, 11, 175 (in Russian).

    CAS  Google Scholar 

  28. V. P. Kulinich, G. P. Shaposhnikov, R. A. Badaukaite, Macroheterocycles, 2010, 3, 23.

    Article  CAS  Google Scholar 

  29. S. A. Znoiko, A. S. Kambolova, V. E. Maizlish, G. P. Shaposhnikov, I. G. Abramov, S. I. Filimonov, Russ. J. Gen. Chem. (Engl. Transl.), 2009, 79, 1735 [Zh. Obshch. Khim., 2009, 79, 1376].

    Article  CAS  Google Scholar 

  30. K. Sakamoto, E. Ohno-Okumura, Materials, 2009, 2, 1127.

    Article  CAS  Google Scholar 

  31. A. Vashurin, A. Filippova, S. Znoyko, A. Voronina, O. Lefedova, I. Kuzmin, V. Maizlish, O. Koifman, J. Porphyrins and Phthalocyanines, 2015, 19, 983.

    Article  CAS  Google Scholar 

  32. A. Filippova, A. Voronina, A. Vashurin, N. Litova, M. Razumov, S. Pukhovskaya, Eur. Chem. Bull., 2014, 3, 1055.

    Google Scholar 

  33. H. L. Anderson, C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Am. Chem. Soc., 1990, 112, 5780.

    Article  CAS  Google Scholar 

  34. J. K. Joseph, S. L. Jain, B. Sain, Ind. Eng. Chem. Res., 2010, 49, 6674.

    Article  CAS  Google Scholar 

  35. A. Vashurin, V. Maizlish, S. Pukhovskaya, A. Voronina, I. Kuzmin, N. Futerman, O. Golubchikov, O. Koifman, J. Porphyrins and Phthalocyanines, 2015, 19, 573.

    Article  CAS  Google Scholar 

  36. A. B. Sorokin, Chem. Rev., 2013, 113, 8152.

    Article  CAS  Google Scholar 

  37. Handbook of Porphyrin Science, Vol. 6, NMR and EPR Techniques, Eds K. M. Kadish, K. M. Smith, R. Guilard, World Scientific, Singapore, 2010.

  38. A. A. Voronina, I. A. Kuzmin, A. S. Vashurin, G. P. Shaposhnikov, S. G. Pukhovskaya, O. A. Golubchikov, Russ. J. Gen. Chem. (Engl. Transl.), 2014, 84, 1777 [Zh. Obshch. Khim., 2014, 84, 1540].

    Article  CAS  Google Scholar 

  39. A. Voronina, A. Vashurin, N. Litova, M. Shepelev, S. Pukhovskaya, Izv. Vuz. Khim. Khim. Tekhnol. [Bulletin of Higher Educational Institutions. Chemistry and Chemical Technology], 2014, 57, 51 (in Russian)].

    CAS  Google Scholar 

  40. I. Ya. Bernshtein, Yu. L. Kaminskii, Spektrofotometricheskii analiz v organicheskoi khimii [Spectrophotometric Analysis in Organic Chemistry], Moscow, Khimiya, 1986, 200 pp. (in Russian).

    Google Scholar 

  41. A. A. Voronina, A. A. Filippova, A. S. Vashurin, S. G. Pukhovskaya, O. A. Golubchikov, G. P. Shaposhnikov, Russ. J. Gen. Chem. (Engl. Transl.), 2015, 85, 1195 [Zh. Obshch. Khim., 2015, 85, 1713].

    Article  Google Scholar 

  42. A. A. Voronina, A. A. Filippova, S. A. Znoiko, A. S. Vashurin, V. E. Maizlish, Russ. J. Inorg. Chem. (Engl. Transl.), 2015, 60, 1407 [Zh. Neorg. Khim., 2015, 60, 1537].

    Article  CAS  Google Scholar 

  43. E. P. Zhiltsova, T. N. Pashirova, R. R. Kashapov, N. K. Gaisin, O. I. Gnezdilov, S. S. Lukashenko, A. D. Voloshina, N. V. Kulik, V. V. Zobov, L. Ya. Zakharova, A. I. Konovalov, Russ. Chem. Bull. (Int. Ed.), 2012, 64, 113 [Izv. Akad. Nauk, Ser. Khim., 2012, 110].

    Article  Google Scholar 

  44. D. W. Dixon, V. Steullet, J. Inorg. Biochem., 1998, 69, 25.

    Article  CAS  Google Scholar 

  45. E. N. Ovchenkova, T. N. Lomova, Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 1581 [Zh. Org. Khim., 2011, 47, 1551].

    Article  CAS  Google Scholar 

  46. A. Voronina, A. Filippova, M. Razumov, I. Kuzmin, M. Shepelev, A. Vashurin, O. Golubchikov, Eur. Chem. Bull., 2015, 4, 335.

    CAS  Google Scholar 

  47. J. S. Craw, S. P. Greatbanks, I. H. Hillier, Ma. J. Harrison, N. A. Burton, J. Chem. Phys., 1997, 106, 6612.

    Article  CAS  Google Scholar 

  48. H. Yamomoto, Ch. Ohira, T. Aso, W. Pfleiderer, Bull. Chem. Soc. Jpn, 1987, 60, 4115.

    Article  Google Scholar 

  49. H. Krawczyk, A. Pietras, J. Mol. Struct., 2008, 882, 116.

    Article  CAS  Google Scholar 

  50. H. Krawczyk, A. Pietras, A. Kraska, Spectrochim. Acta, Part A, 2007, 66, 9.

    Article  Google Scholar 

  51. E. M. Tyapochkin, E. I. Kozliak, J. Mol. Catal.A: Chem., 2005, 242, 1.

    Article  CAS  Google Scholar 

  52. A. S. Vashurin, S. G. Pukhovskaya, A. S. Semeikin, O. A. Golubchikov, Macroheterocycles, 2012, 5, 72.

    Article  CAS  Google Scholar 

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  1. Ivanovo State University for Chemistry and Technology, Institute of Chemistry of Macroheterocyclic Compounds, 7 Sheremetevskii prosp., 153000, Ivanovo, Russian Federation

    A. S. Vashurin

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Correspondence to A. S. Vashurin.

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Based on the materials of the International Congress on the Heterocyclic Chemistry "KOST-2015" (October 17—23, 2015, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2220—2228, September, 2016.

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Vashurin, A.S. Non-covalent associates of metal phthalocyanines: the role of axial ligand and catalytic activity. Russ Chem Bull 65, 2220–2228 (2016). https://doi.org/10.1007/s11172-016-1572-z

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  • DOI: https://doi.org/10.1007/s11172-016-1572-z

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