Abstract
The molecules oftrans-isomer of styryl dye1a, containing the benzo-18-crown-6 moiety and the methoxybenzothiazole residue with theN-octadecyl substituent, were shown to form stable, highly ordered monolayers at the water/air interface. Increasing the surface pressure of the monolayer results in the formation of the H-aggregated molecules of compound1a. The H-aggregates tend to dissociate to the monomerictrans-form, when the monolayer forms in the Langmuir-Blodgett film (LB film). The light irradiation of the LB films leads to the partially reversibletrans-cis-photoisomerization of compound1a, whose efficiency is much lower than that observed in an acetonitrile solution of1a. The aggregation of cis-1a isomers in the LB film is suggested to hamper the reversecis-trans-isomerization. The aggregation oftrans-1a molecules in the LB films does not occur in air, but, after dipping in an aqueous solution, molecules of the LB film slowly form J-aggregates. A model of the structural organization oftrans-1a molecules in the LB films was proposed.
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References
F. Voegtle,Supramolekulare Chemie, Ed. B. G. Teubner, Stuttgart, 1989.
E. Weber,Crown-ether and Analogs, Eds. S. Patai and Z.Rappoport, John Wiley & Sons, New York, 1989, 305.
G. W. Gokel and S. H. Korzeniowski,Macrocyclic Polyether Syntheses, Springer-Verlag, Berlin, 1982.
Yu. A. Ovchinnikov, V. T. Ivanov, and A. M. Shkrob,Membrane-active Complexones, Elsevier, Amsterdam, 1974.
K. Kimura and T. Shono,Cation Binding by Macrocycles: Complexation of Cationic Species by Crown-ethers, Eds. Y. Inoue and G. W. Gokel, Marcel Dekker, Inc., New York, 1990, 429.
E. Blasius and K.-P. Janzen,Kost Guest Complex Chemistry. Macrocycles: Synthesis, Structures, Applications, Eds. F. Voegtle and E. Weber, Springer-Verlag, Berlin, 1985, 189.
M. Sugawara, M. Kataoka, K. Odashima, and Y. Umezawa,Thin Solid Films, 1989,180, 129.
V. V. Lapachev, S. A. Stekhova, E. G. Lubenets, and V. S. Kobrin,Sib. Khim. Zh. [Siberian Chem. J.], 1992,2, 94 (in Russian).
S. M. Balashov, V. V. Kislov, V. V. Lapachev, I. E. Nevernov, A. Yu. Potapov, and G. B. Khomutov,Biol. Membrany [Biol. Membranes], 1990,7, 1205 (in Russian).
U. Z. Mirkhodzhaev, Kh. F. Abdullaev, and A. K. Tashmukhamedova,Uzb. Biol. Zh. [Uzbekistan Biol. J.], 1990,5, 61 (in Russian).
Z. Q. Yao, P. Liu, R. Z. Yan, L. Y. Liu, X. H. Liu, and W. C. Wang,Thin Solid Films. 1992,210/211, 208.
X. Zhang, Z. Lin, J. Shen, and X. I. Tang,Thin Solid Films, 1992,210/211, 628.
Y.-M. Zhu and Yu Wei,J. Chem. Phys., 1994,101, 10023.
M. Takagi,Cation Binding by Macrocycles: Complexation of Cationic Species by Crown-ethers, Eds. Y. Inoue and G. W. Gokel, Marcel Dekker, Inc., New York, 1990, 465.
S. Shinkai and O. Manabe,Host Guest Complex Chemistry. Macrocycles: Synthesis, Structures, Applications, Eds. F. Voegtle and E. Weber, Springer-Verlag, Berlin, 1985, 245.
S. Shinkai,Cation Binding by Macrocycles: Complexation of Cationic Species by Crown-ethers, Eds. Y. Inoue and G. W. Gokel, Marcel Dekker, Inc., New York, 1990, 397.
J.-M. Lehn,Angew. Chem. Int. Ed. Engl., 1990,29, 1304.
M. V. Alfimov, I. K. Lednev, and S. P. Gromov,Chem. Phys. Lett., 1991,185, 455.
S. P. Gromov, M. V. Fornina, G. K. Chudinova, V. A. Barachevskii, and M. V. Alfimov,Dokl. Akad. Nauk SSSR, 1991,321, 739 [Dokl. Chem. SSSR, 1991,321 (Engl. Transl.)].
O. Fedorova, S. Gromov, M. Fomina, G. Chudinova, V. Savransky, V. Barachevsky, and M. Alfimov,The Seventh International Conference on Organized Molecular Films, September 10–15, 1995, P-83, 108.
S. Yu. Zaitsev, V. V. Lytsenko, and V. P. Zubov,Bioorg. Khim., 1983,9, 567 [Bioarg. Chem., 1983,9 (Engl. Transl.)].
H.-J. Winter and G. Manecke,Macromol. Chem., 1985,186, 1979.
I. K. Lednev and M. C. Petty,Advanced Materials for Optics and Eletronics, 1992,4, 225.
S. Yu. Zaitsev, M. Belohradsky, J. Zavada, and D. Moebius,Thin Solid Films, 1994,248, 78.
C. Jennings, G. J. Kovacs, and R. Aroca, inProc. 13 Intern. Conf on Raman Spectrosc., Eds. W. Kiefer and M. Cardona, Wiley, 1992, 640.
S. Yu. Zaitsev, N. A. Kalabina, V. P. Zubov, G. Chumanov, D. Gaul, and T. M. Cotton,Colloids and Surf A: Physicochem. and Engineering Aspects, 1993,78, 211.
T. Terashita, Y. Wang, Y. Ozaki, and K. Iriyama, inProc. 14 Intern. Conf on Raman Spectrosc., Eds. N.-T. Yu and X.-Y. Li, Wiley, Hong Cong, 1994, 672.
A. Feofanov, A. Yanol, V. Oleinikov, S. Gromov, O. Fedorova, M. Alfimov, and I. Nabiev,J. Phys. Chem., 1996,100, 2154.
A. V. Feofanov, A. I. Yanul', V. A. Oleinikov, I. R. Nabiev, S. P. Gromov, O. A. Fedorova, and M. V. Alfimov,Izv. Akad. Nauk, Ser. Khim., 1995, 2429 [Russ. Chem. Bull., 1995,44, 2323 (Engl. Transl.)].
M. V. Alfimov and S. P. Gromov,NATO ASI Ser., Ser. C, 1992,371, 343.
F. Wada, H. Hiroayama, H. Namiki, H. Kikukawa, and T. Matsuda,Bull. Chem. Soc. Jap., 1980,53, 1473.
J. Sondermann,Liebigs Ann. Chem., 1971, 183.
S. Enomoto, Y. Ozakl, and N. Kuramoto,Langmuir, 1993,9, 3219.
N. Katayama, M. Fukui, Y. Ozakl, N. Kuramoto, T. Arakl, and K. Iriyama,Langmuir, 1991,7, 2827
N. Katayama, Y. Ozakl, and N. Kuramoto,Chem. Phys. Lett., 1991,179, 227
D. A. Styrkas, I. K. Lednev, and M. V. Alfimov,Dokl. Akad. Nauk SSSR, 1990,312, 407 [Dokl. Chem. SSSR, 1990,312, (Engl. Transl.].
D. Mobius,D. Acc. Chem. Res., 1981,14, 63
H. Kuhn, B. Mann, H. Bucher, D. Mobius, L. V. Szentpaly, and P. Tillmann,Photogr. Sci. Eng., 1967,11, 233.
H. Kuhn,Pure Appl. Chem., 1979,51, 341.
H. Nakahara, K. Fukuda, D. Mobius, and H. Kuhn.J. Phys. Chem., 1986,90, 6144
I. K. Lednev and M.C. Petty,Langmuir, 1994,10, 4185.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2490–2496, October, 1996.
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Kryukov, E.V., Feofanov, A.V., Oleinikov, V.A. et al. Aggregation and photoisomerization of amphiphilic crown-ether styryl dye in monolayers at the interface. Russ Chem Bull 45, 2362–2368 (1996). https://doi.org/10.1007/BF01435383
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DOI: https://doi.org/10.1007/BF01435383