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Synthesis of 2,8,12,18-tetrabutyl-3,7,13,17-tetramethyl-5-{3-[11-(pyridin-4-yloxy)-3,6,9-trioxaundecyloxy]phenyl}-porphyrin and study on the effect of its molecular conformation on physicochemical properties

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Abstract

2,8,12,18-Tetrabutyl-3,7,13,17-tetramethyl-5-{3-[11-(pyridin-4-yloxy)-3,6,9-trioxaundecyloxy] phenyl}porphyrin was synthesized, and its complexation with zinc and potassium cations in the system toluene-methanol (5:1) was studied by spectrophotometric titration and 1H NMR spectroscopy. Spatial preorganization of the meso-aryl substituent due to complex formation of potassium cation with the polyether fragment accelerates the reaction of zinc with the title compound approximately threefold. A probable scheme of the interaction was proposed, and formation constants of the corresponding complexes were determined.

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References

  1. Ogoshi, H., Mizutani, T., Hayashi, T., and Ruroda, Y., The Porphyrin Handbook, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., San Diego: Academic, 2000, vol. 6, p. 280.

    Google Scholar 

  2. Sanders, J.K.M., The Porphyrin Handbook, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., San Diego: Academic, 2000, vol. 3, p. 347.

    Google Scholar 

  3. Wojaczyński, J. and Latos-Grażński, L., Coord. Chem. Rev., 2000, vol. 204, no. 1, p. 133.

    Google Scholar 

  4. Fleischer, E.B. and Shachter, A.M., Inorg. Chem., 1991, vol. 30, no. 19, p. 3763.

    Article  CAS  Google Scholar 

  5. Gardner, M., Guerin, A.J., Hunter, C.A., Michelsen, U., and Rotger, C., New J. Chem., 1999, no. 23, p. 309.

  6. Koifman, O.I., Mamardashvili, N.Zh., and Antipin, I.S., Sinteticheskie retseptory na osnove porfirinov i ikh kon"yugatov s kaliks[4]arenami (Synthetic Receptors on the Basis of Porphyrins and Their Conjugates with Calix[4]arenes), Moscow: Nauka, 2006, p. 246.

    Google Scholar 

  7. Mamardashvili, G.M., Mamardashvili, N.Zh., and Koifman, O.I., Usp. Khim., 2005, vol. 74, no. 8, p. 839.

    Google Scholar 

  8. Berezin, B.D., Koordinatsionnye soedineniya porfirinov i ftalotsianina (Coordination Compounds of Porphyrin and Phthalocyanine), Moscow: Nauka, 1978, p. 279.

    Google Scholar 

  9. Mamardashvili, G.M., Kumeev, R.S., and Mamardashvili, N.Zh., Zh. Neorg. Khim., 2006, vol. 51, no. 8, p. 1349.

    CAS  Google Scholar 

  10. Ivanova, Yu.B., Toldina, O.V., Sheinin, V.B., and Mamardashvili, N.Zh., Russ. J. Org. Chem., 2007, vol. 43, no. 9, p. 1397.

    Article  CAS  Google Scholar 

  11. Toldina, O.V. and Mamardashvili, N.Zh., Abstracts of Papers, IVth Int. Symp. “Design and Synthesis of Supramolecular Architectures,” Kazan (Russia), 2006, p. 106.

  12. Mamardashvili, N.Zh., Abstracts of Papers, XXV nauchnaya sessiya Vserossiiskogo seminara po khimii porfirinov i ikh analogov (XXVth Scientific Session of the All-Russian Seminar on the Chemistry of Porphyrins and Their Analogs), Ivanovo, 2004, p. 13.

  13. Organikum. Organisch-chemisches Grundpraktikum, Berlin: Wissenschaften, 1976, 15th edn. Translated under the title Organikum, Moscow: Mir, 1979, vol. 2, p. 422.

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Correspondence to O. V. Toldina.

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Original Russian Text © O.V. Toldina, N.Zh. Mamardashvili, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 5, pp. 848–853.

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Toldina, O.V., Mamardashvili, N.Z. Synthesis of 2,8,12,18-tetrabutyl-3,7,13,17-tetramethyl-5-{3-[11-(pyridin-4-yloxy)-3,6,9-trioxaundecyloxy]phenyl}-porphyrin and study on the effect of its molecular conformation on physicochemical properties. Russ J Gen Chem 78, 991–996 (2008). https://doi.org/10.1134/S1070363208050265

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  • DOI: https://doi.org/10.1134/S1070363208050265

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