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Hierarchy of Times for Forming the System of Chiral Phases in Solutions of Trifluoroacetylated Amino Alcohols

  • Kinetics and Mechanism of Chemical Reactions. Catalysis
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Abstract

It has been experimentally established that the chiroptical characteristics of freshly prepared solutions of trifluoroacetylated amino alcohols (TFAAAs) evolve before reaching equilibrium. The evolution can be monotone or quasi-oscillatory. The latter reflects the formation of successive levels of the hierarchy of chiral phases with an alternating sign of chirality in the solution. The fast (the characteristic time τ from ~30 s to ~30 min) and slow (τ ~ 1–3 h) stages of evolution have been experimentally revealed. It is shown via calculation that the fast stage corresponds to the early stages of the formation of the supramolecular structure of the solutions of TFAAAs, namely, the growth of strings with diameters from several nanometers to tenths of a micrometer, while the slow stage corresponds to the late stages in the formation of the structure of the solutions, namely, the growth of strings with diameters from tenths of a micrometer up to several micrometers.

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References

  1. L. Lu and R. G. Weiss, Langmuir 11, 3630 (1995).

    Article  CAS  Google Scholar 

  2. K. Inoue, Y. Ono, Y. Kanekiyo, et al., J. Org. Chem. 64, 2933 (1999).

    Article  CAS  PubMed  Google Scholar 

  3. S. Laan, B. L. Feringa, R. M. Kellogg, et al., Langmuir 18, 7136 (2002).

    Article  CAS  Google Scholar 

  4. S. Vauthey, S. Santoso, H. Gong, et al., Proc. Natl. Acad. Sci. U.S.A. 99, 5355 (2002).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. C. Li, N. J. Buurma, I. Haq, et al., Langmuir 21, 11026 (2005).

    Article  CAS  PubMed  Google Scholar 

  6. C. Zhan, P. Gao, and M. Liu, Chem. Commun., 462 (2005).

    Google Scholar 

  7. M. George, G. P. Funkhouser, P. Terech, et al., Langmuir 22, 7885 (2006).

    Article  CAS  PubMed  Google Scholar 

  8. S. J. Langford, M. J. Latter, V. L. Lau, et al., Org. Lett. 8, 1371 (2006).

    Article  CAS  PubMed  Google Scholar 

  9. G. Godeau and D. Barthelemy, Langmuir 25, 8447 (2009).

    Article  CAS  PubMed  Google Scholar 

  10. C. C. Lee, C. Grenier, E. W. Meijer, et al., Chem. Soc. Rev. 38, 671 (2009).

    Article  CAS  PubMed  Google Scholar 

  11. J. Madsen, S. P. Armes, K. Bertal, et al., Biomacromolecules 10, 1875 (2009).

    Article  CAS  PubMed  Google Scholar 

  12. B. G. Bag, G. C. Maity, and S. R. Pramanik, Supramol. Chem. 17, 383 (2010).

    Article  CAS  Google Scholar 

  13. A. A. Bredikhin, Z. A. Bredikhina, and A. V. Pashagin, Mendeleev Commun. 21, 144 (2011).

    Article  CAS  Google Scholar 

  14. R. G. Weiss and P. Terech, Molecular Gels (Springer, Dordecht, 2006).

    Book  Google Scholar 

  15. P. de Gennes, Scaling Concepts in Polymer Physics (Cornell Univ. Press, Ithaca, 1979).

    Google Scholar 

  16. D. Stauffer, Introduction to Percolation Theory (Taylor and Francis, London, 1985).

    Book  Google Scholar 

  17. M. Kleman and O. D. Lavrentovich, Soft Matter Physics (Springer, New York, 2003).

    Google Scholar 

  18. S. V. Stovbun, Doctoral (Phys. Math.) Dissertation (Moscow, 2012).

    Google Scholar 

  19. O. Lebel, M. E. Perron, T. Maris, et al., Chem. Mater. 18, 3616 (2006).

    Article  CAS  Google Scholar 

  20. G. John, B. V. Shankar, S. R. Jadhav, and P. K. Vemula, Langmuir 26, 17843 (2010).

    Article  CAS  PubMed  Google Scholar 

  21. M. George and R. G. Weiss, Langmuir 19, 8168 (2003).

    Article  CAS  Google Scholar 

  22. M. George and R. G. Weiss, Acc. Chem. Res. 39, 489 (2006).

    Article  CAS  PubMed  Google Scholar 

  23. J. Peng, K. Liu, J. Liu, et al., Langmuir 24, 2992 (2008).

    Article  CAS  PubMed  Google Scholar 

  24. S. Prasanthkumar, A. Saeki, S. Seki, and A. Ajayaghosh, J. Am. Chem. Soc. 132, 8866 (2010).

    Article  CAS  PubMed  Google Scholar 

  25. X. Huang, P. Terech, S. R. Raghavan, et al., J. Am. Chem. Soc. 127, 4336 (2005).

    Article  CAS  PubMed  Google Scholar 

  26. R. G. Kostyanovsky, D. F. Lenev, O. N. Krutius, et al., Mendeleev Commun. 15, 140 (2005).

    Article  CAS  Google Scholar 

  27. S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 317 (2012).

    Article  Google Scholar 

  28. S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 274 (2012).

    Article  Google Scholar 

  29. S. V. Stovbun, A. M. Zanin, A. A. Skoblin, F. V. Bulygin, V. S. Fedorenko, V. L. Lyaskovskii, and I. A. Bilenko, Meas. Tech. 55, 734 (2012).

    Article  CAS  Google Scholar 

  30. S. V. Stovbun and A. A. Skoblin, Khim. Fiz. 31 (9), 24 (2012).

    CAS  Google Scholar 

  31. S. V. Stovbun, A. M. Zanin, A. A. Skoblin, A. I. Mikhailov, R. G. Kostyanovskii, M. V. Grishin, and B. R. Shub, Russ. J. Phys. Chem. B 6, 1019 (2012).

    Google Scholar 

  32. S. V. Stovbun, A. A. Skoblin, and A. I. Mikhailov, Khim. Fiz. 32 (2), 30 (2013).

    CAS  Google Scholar 

  33. S. V. Stovbun, A. A. Skoblin, A. M. Zanin, et al., Khim. Fiz. 32 (3), 12 (2013).

    CAS  Google Scholar 

  34. S. V. Stovbun, A. A. Skoblin, A. M. Zanin, Y. A. Litvin, A. A. Kirsankin, M. V. Grishin, B. R. Shub, and V. A. Tverdislov, Russ. J. Phys. Chem. B 8, 620 (2014).

    Article  CAS  Google Scholar 

  35. S. V. Stovbun, Russ. J. Phys. Chem. B 5, 546 (2011).

    Article  CAS  Google Scholar 

  36. S. V. Stovbun, O. N. Krutius, A. M. Zanin, D. S. Skorobogat’ko, and R. G. Kostyanovskii, Russ. J. Phys. Chem. B 5, 846 (2011).

    Article  CAS  Google Scholar 

  37. S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 317 (2012).

    Article  Google Scholar 

  38. S. V. Stovbun, A. M. Zanin, A. A. Skoblin, A. I. Mikhailov, and A. A. Berlin, Dokl. Phys. Chem. 442, 36 (2012).

    Article  CAS  Google Scholar 

  39. S. V. Stovbun, A. A. Skoblin, A. I. Mikhailov, et al., Nanotechnol. Russ. 7, 531 (2012).

    Article  Google Scholar 

  40. S. V. Stovbun, A. M. Zanin, A. A. Skoblin, D. P. Shashkin, A. I. Mikhailov, M. V. Grishin, and B. R. Shub, Russ. J. Phys. Chem. B 7, 1 (2013).

    Article  CAS  Google Scholar 

  41. S. V. Stovbun, A. A. Skoblin, and A. A. Berlin, Dokl. Phys. Chem. 450, 111 (2013).

    Article  CAS  Google Scholar 

  42. Ya. A. Litvin, A. A. Skoblin, and S. V. Stovbun, Russ. J. Phys. Chem. B 11, 146 (2017).

    Article  CAS  Google Scholar 

  43. S. V. Stovbun, A. M. Zanin, A. A. Skoblin, A. I. Mikhailov, R. G. Kostyanovskii, M. V. Grishin, and B. R. Shub, Russ. J. Phys. Chem. B 5, 1023 (2011).

    Article  CAS  Google Scholar 

  44. S. V. Stovbun, A. A. Skoblin, A. M. Zanin, M. V. Grishin, B. R. Shub, Yu. M. Rybin, I. M. Ageev, G. G. Shishkin, and V. A. Tverdislov, Bull. Exp. Biol. Med. 154, 34 (2012).

    Article  CAS  PubMed  Google Scholar 

  45. S. V. Stovbun, A. A. Skoblin, A. M. Zanin, D. P. Shashkin, A. A. Berlin, and V. A. Tverdislov, Dokl. Phys. Chem. 450, 138 (2013).

    Article  CAS  Google Scholar 

  46. D. V. Zlenko and S. V. Stovbun, Russ. J. Phys. Chem. B 8, 613 (2014).

    Article  CAS  Google Scholar 

  47. Y. A. Litvin, A. N. Shchegolikhin, A. A. Skoblin, and S. V. Stovbun, Russ. J. Phys. Chem. B 10, 725 (2016).

    Article  CAS  Google Scholar 

  48. S. V. Stovbun, A. A. Skoblin, Y. A. Litvin, A. A. Kirsankin, M. V. Grishin, B. R. Shub, Y. V. Zubavichus, A. A. Veligzhanin, L. D. Popov, E. A. Raspopova, and Y. N. Tkachenko, Russ. J. Phys. Chem. B 8, 801 (2014).

    Article  CAS  Google Scholar 

  49. S. V. Stovbun, A. A. Skoblin, J. A. Litvin, M. G. Mikhaleva, and V. A. Tverdislov, Mosc. Univ. Phys. Bull. 70, 45 (2015).

    Article  Google Scholar 

  50. A. A. Skoblin and S. V. Stovbun, Bull. Exp. Biol. Med. 159, 607 (2015).

    Article  CAS  PubMed  Google Scholar 

  51. S. V. Stovbun, A. A. Skoblin, F. V. Bulygin, V. L. Minaev, V. O. Kompanets, V. B. Laptev, E. A. Ryabov, S. V. Chekalin, and S. E. Permyakov, Russ. J. Phys. Chem. B 9, 193 (2015).

    Article  CAS  Google Scholar 

  52. S. V. Stovbun, A. A. Skoblin, and A. M. Zanin, Russ. J. Phys. Chem. B 8, 293 (2014).

    Article  CAS  Google Scholar 

  53. A. A. Skoblin, A. M. Zanin, and S. V. Stovbun, Russ. J. Phys. Chem. B 8, 302 (2014).

    Article  CAS  Google Scholar 

  54. S. V. Stovbun, V. A. Tverdislov, and A. A. Skoblin, Biophysics 59, 876 (2014).

    Article  CAS  Google Scholar 

  55. S. V. Stovbun, A. M. Zanin, A. A. Skoblin, M. G. Mikhaleva, D. V. Zlenko, and V. A. Tverdislov, Mosc. Univ. Phys. Bull. 70, 51 (2015).

    Article  Google Scholar 

  56. S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 278 (2012).

    Article  Google Scholar 

  57. S. V. Stovbun, A. M. Zanin, D. S. Skorobogat’ko, A. A. Skoblin, Ya. A. Litvin, A. I. Mikhailov, O. N. Krutius, and R. G. Kostyanovskii, Russ. J. Phys. Chem. B 6, 341 (2012).

    Article  CAS  Google Scholar 

  58. S. V. Stovbun and A. A. Skoblin, Khim. Fiz. 31 (7), 7 (2012).

    CAS  Google Scholar 

  59. V. A. Tverdislov, Biophysics 58, 128 (2013).

    Article  CAS  Google Scholar 

  60. V. A. Tverdislov, L. V. Yakovenko, A. A. Ivlieva, and I. L. Tverdislova, Mosc. Univ. Phys. Bull. 66, 105 (2011).

    Article  Google Scholar 

  61. V. A. Tverdislov, A. E. Sidorova, and L. V. Yakovenko, Biophysics 57, 120 (2012).

    Article  CAS  Google Scholar 

  62. V. A. Tverdislov and E. V. Malyshko, Slozhnost’. Razum. Postneklassika, No. 1, 78 (2016).

    Google Scholar 

  63. V. A. Tverdislov, E. V. Malyshko, S. A. Il’chenko, O. A. Zhulyabina, and L. V. Yakovenko, Biophysics 62, 331 (2017).

    Article  CAS  Google Scholar 

  64. S. V. Stovbun, V. A. Tverdislov, and A. A. Skoblin, Biophysics 59, 876 (2014).

    Article  CAS  Google Scholar 

  65. S. V. Stovbun, A. A. Skoblin, and V. A. Tverdislov, Bull. Exp. Biol. Med. 152, 703 (2012).

    Article  CAS  PubMed  Google Scholar 

  66. S. V. Stovbun, Bull. Exp. Biol. Med. 152, 50 (2011).

    Article  CAS  PubMed  Google Scholar 

  67. S. V. Stovbun and A. A. Skoblin, Bull. Exp. Biol. Med. 152, 571 (2012).

    Article  CAS  PubMed  Google Scholar 

  68. S. V. Stovbun, A. I. Mikhailov, A. A. Skoblin, E. E. Bragina, and M. A. Gomberg, Russ. J. Phys. Chem. B 6, 60 (2012).

    Article  CAS  Google Scholar 

  69. S. V. Stovbun, A. A. Skoblin, A. M. Zanin, A. I. Mikhailov, V. A. Tverdislov, E. E. Bragina, Yu.M. Rybin, I. M. Ageev, and G. G. Shishkin, Bull. Exp. Biol. Med. 153, 844 (2012).

    Article  Google Scholar 

  70. S. V. Stovbun, S. N. Nikol’skii, V. P. Mel’nikov, M. G. Mikhaleva, Y. A. Litvin, A. N. Shchegolikhin, D. V. Zlenko, V. A. Tverdislov, D. S. Gerasimov, and A. D. Rogozin, Russ. J. Phys. Chem. B 10, 245 (2016).

    Article  CAS  Google Scholar 

  71. S. V. Stovbun, S. M. Lomakin, A. I. Shchegolikhin, et al., Khim. Fiz. 37 (1), 21 (2017).

    Google Scholar 

  72. G. S. Landsberg, Optics (Fizmatlit, Moscow, 2006) [in Russian].

    Google Scholar 

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Correspondence to M. G. Mikhaleva.

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Original Russian Text © M.A. Tregubova, M.G. Mikhaleva, A.A. Kirsankin, S.N. Nikolskij, 2018, published in Khimicheskaya Fizika, 2018, Vol. 37, No. 6, pp. 32–43.

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Tregubova, M.A., Mikhaleva, M.G., Kirsankin, A.A. et al. Hierarchy of Times for Forming the System of Chiral Phases in Solutions of Trifluoroacetylated Amino Alcohols. Russ. J. Phys. Chem. B 12, 426–437 (2018). https://doi.org/10.1134/S1990793118030314

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