Abstract
The model of a homochiral string (from N-trifluoroacetyl-2-amino-3-methylpentanol-1 molecules) is based on experimental data molecular dynamics simulation results. The resulting model string is a hollow stable helix with characteristics consistent with the available experimental data. It is shown that the main contribution to the formation of the string comes from the dispersion interaction (∼0.5 eV) of the homochiral molecules in complementary stacks. In this case, neighboring molecular dipoles are anticollinear, whereas the string is antiferroelectric.
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References
G. Godeau and D. Barthelemy, Langmuir 25, 8447 (2009).
M. George and R. G. Weiss, Acc. Chem. Res. 39, 489 (2006).
A. A. Bredikhin, Z. A. Bredikhina, and A. V. Pashagin, Mendeleev Commun. 21, 144 (2011).
C. Li, N.J. Buurma, I. Haq, C. Turner, and S. P. Armes, Langmuir 21, 11026 (2005).
J. Peng, K. Liu, J. Liu, et al., Langmuir 24, 2992 (2008).
A. Gansäuer, I. Winkler, T. Klawonn, et al., Organometallics 28, 1377 (2008).
A. R. Hirst, I. A. Coates, T. R. Boucheteau, et al., J. Am. Chem. Soc. 130, 9113 (2008).
C. C. Lee, C. Grenier, E. W. Meijer, and A. P. H. J. Schenning, Chem. Soc. Rev. 38, 671 (2009).
S. Vauthey, S. Santoso, H. Gong, N. Watson, S. Zhang, Proc. Nat. Acad. Sci. 99, 5355 (2002).
M. George and R. G. Weiss, Langmuir 19, 1017 (2003).
M. George, G. P. Funkhouser, P. Terech, and R. G. Wise, Langmuir 22, 7885 (2006).
M. George and R. G. Weiss, J. Am. Chem. Soc. 123, 10393 (2001).
S. Laan, B. L. Feringa, R. M. Kellogg, and J. Esch, Langmuir 18, 7136 (2002).
K. Inoue, Y. Ono, Y. Kanekiyo, et al., Org. Chem. 64, 2933 (1999).
B. G. Bag, G. C. Maity, and S. R. Pramanik, Supramol. Chem. 17, 383 (2010).
J. Madsen, S. P. Armes, K. Bertal, S. MacNeil, and A. L. Lewis, Biomacromolecules 10, 1875 (2009).
C. Zhan, P. Gao, and M. Liu, Chem. Commun., 462 (2005).
P. Terech and R. G. Weiss, Chem. Rev. 97, 3133 (1997).
S. J. Langford, M. J. Latter, V. L. Lau, et al., Org. Lett. 8, 1371 (2006).
L. Lu and R. G. Weiss, Langmuir 11, 3630 (1995).
S. V. Stovbun, A. M. Zanin, A. A. Skoblin, A. I. Mikhailov, and A. A. Berlin, Dokl. Phys. Chem. 442, 36 (2012).
S. V. Stovbun, Russ. J. Phys. Chem. B 5, 546 (2011).
S. V. Stovbun, A. A. Skoblin, A. I. Mikhailov, et al., Nanotechnol. Russia 7, 531 (2012).
S. S. Stovbun, A. A. Skoblin, and A. A. Berlin, Dokl. Phys. Chem. 450, 111 (2013).
S. V. Stovbun, A. M. Zanin, A. A. Skoblin, et al., Russ. J. Phys. Chem. B 5, 1019 (2011).
S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 274 (2012).
S. V. Stovbun, A. M. Zanin, D. S. Skorobogat’ko, et al., Russ. J. Phys. Chem. B 6, 341 (2012).
S. V. Stovbun, A. A. Skoblin, A. M. Zanin, et al., Vestn. MGOU, Ser. Estestv. Nauki, No. 2, 55 (2012).
W. L. Jorgensen, D. S. Maxwell, and J. Tirado-Rives, J. Am. Chem. Soc. 118, 11225 (1996).
C. I. Bayly, P. Cieplak, W. Cornell, and P. A. Kollman, J. Phys. Chem. 97, 10269 (1993).
A. A. Granovsky, Firefly, Vers. 7.1.G. http://classic.chem.msu.su/gran/firefly/index.html
S. Pronk, S. Páll, R. Schulz, et al., Bioinformatics 29, 845 (2013).
S. V. Stovbun, A. M. Zanin, A. A. Skoblin, et al., Khim. Fiz. 33 (1), 44 (2014).
N. Ben-Tal, D. Sitkoff, I. A. Topol, et al., J. Phys. Chem. B 101, 450 (1997).
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Original Russian Text © D.V. Zlenko, S.V. Stovbun, 2014, published in Khimicheskaya Fizika, 2014, Vol. 33, No. 9, pp. 3–10.
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Zlenko, D.V., Stovbun, S.V. Model of a homochiral supramolecular string. Russ. J. Phys. Chem. B 8, 613–619 (2014). https://doi.org/10.1134/S199079311405011X
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DOI: https://doi.org/10.1134/S199079311405011X