Abstract
Mixed micellization of amphiphilic aminomethylated calix[4]resorcinarenes and phenols, which are their structural units, with the cationic surfactant cetyltrimethylammonium bromide (CTAB) in aqueous 10—70 vol % DMF decreases the critical micelle concentration; the resulting aggregates are larger than those in the CTAB—DMF—water systems. The micellization of CTAB with aminomethylated calix[4]resorcinarenes proceeds in two steps, while its micellization with phenols is a single-step process. The micellization characteristics depend on the structure and hydrophobicity of the amphiphilic compound and the concentration of DMF.
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References
J. H. Fendler, Chem. Rev., 1987, 87, 877.
J. M. Lehn, Supramolecular Chemistry. Concepts and Perspectives, VCH Verlagsgesellschaft mbH, Weinheim-New York-Basel-Cambridge-Tokyo, 1995.
S. M. Bystryak and M. A. Winnik, Langmuir, 1999, 15, 3747.
P. Choppinet, L. Jullien, and B. Valeur, Perkin Trans. 2, 1999, 249.
M. S. J. Barshi, Dispers. Sci. Technol., 2000, 21, 615.
M. Nishida, M. Sonoda, D. Ishii, and I. Yoshida, Chem. Lett., 1998, 289.
M. Nakagaki, K. Inoue, H. Komotsu, T. Handa, and K. Miyajima, Chem. Pharm. Bull., 1988, 36, 2742.
S. Arimori, T. Nagasali, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1995, 679.
N. Kimizuka, T. Wakiama, A. Yanagi, S. Shinkai, and T. Kunitake, Bull. Chem. Soc. Jpn., 1996, 69, 3681.
F. Kh. Karataeva, A. I. Rakhmatullin, F. V. Aganov, Yu. E. Morozova, and E. Kh. Kazakova, Zh. Obshch. Khim., 1998, 68, 837 [Russ. J. Gen. Chem., 1998, 68 (Engl. Transl.)].
A. Lucke, C. J. V. Stirling, and V. Bohmer, in Calixarenes 2001, Eds. Z. Asfari, V. Bohmer, J. Harrowfield, and J. Vicens, Kluwer Academic Publishers, Dordrecht-Boston-London, 2001, p. 613.
I. S. Ryzhkina, Ya. A. Babkina, S. S. Lukashenko, K. M. Enikeev, L. A. Kudryavtseva, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 2002, 2026 [Russ. Chem. Bull.,Int. Ed., 2002, 51, 2183 ].
I. S. Ryzhkina, L. A. Kudryavtseva, A. R. Burilov, E. Kh. Kazakova, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 1998, 275 [Russ. Chem. Bull., 1998, 47, 269 (Engl. Transl.)].
I. S. Ryzhkina, L. A. Kudryavtseva, Ya. A. Babkina, K. M. Enikeev, M. A. Pudovik, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 2000, 1361 [Russ. Chem. Bull., 2000, 49, 1355 (Engl. Transl.)].
B. Reichert, Die Mannich Reaktion, Springer Verlag, Berlin-Göttingen-Heidelberg, 1959, 192 pp.
Y. Matsuskita and T. Matsui, Tetrahedron Lett., 1993, 34, 7433.
E. V. Popova, A. R. Burilov, M. A. Pudovik, V. D. Khabikher, and A. I. Konovalov, Zh. Obshch. Khim., 2002, 72, 1049 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)].
I. S. Ryzhkina, L. A. Kudryavtseva, A. R. Burilov, E. Kh. Kazakova, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 1999, 456 [Russ. Chem. Bull., 1999, 48, 453 (Engl. Transl.)].
Micellization, Solubilization, and Microemulsions, Ed. K. L. Mittal, Plenum Press, New York-London, 1977.
V. D. Fedotov, Yu. F. Zuev, V. P. Archipov, and Z. Sh. Idiyatullin, Appl. Magn. Res., 996, 11, 7.
S. Shinkai, S. Mori, H. Koreishi, T. Tsubaki, and O. Manabe, J. Am. Chem. Soc., 1986, 108, 2409.
E. P. Zhil'tsova, A. P. Timosheva, R. A. Shagidullina, A. R. Mustafina, L. A. Kudryavtseva, V. E. Kataev, E. Kh. Kazakova, V. F. Nikolaev, and A. I. Konovalov, Zh. Obshch. Khim., 2001, 71, 419 [Russ. J. Gen. Chem., 2001, 71 (Engl. Transl.)].
A. A. Shakhatuni and A. G. Shakhatuni, Usp. Khim., 2002, 71, 1132 [Russ. Chem. Rev., 2002, 71 (Engl. Transl.)].
D. Eisenberg and W. Kauzmann, Struktura i svoistva vody [Water:Structure and Properties], Ed. V. V. Bogorodskii, Gidrometeoizdat, Leningrad, 1975 (in Russian).
A. W. Coleman, S. G. Bott, S. D. Morley, C. M. Means, K. D. Robinson, H. Zhang, and J. L. Atwood, Angew. Chem., 1988, 100, 1412.
W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw Hill Book Co., New York, 1969.
J. E. Gordon, The Organic Chemistry of Electrolyte Solutions, Wiley Interscience Publication, John Wiley and Sons, New York, 1975.
A. D. Pidwell, S. R. Collinson, S. J. Coles, M. B. Harsthouse, M. Schroder, and D. W. Bruce, Chem. Commun., 2000, 955.
A. I. Serdyuk and R. V. Kucher, Mitsellyarnye perekhody v rastvorakh poverkhnostno aktivnykh veshchestv [Micellar Transitions in Surfactant Solutions], Naukova Dumka, Kiev, 1987, 208 pp. (in Russian).
R. F. Bakeeva, D. B. Kudryavtsev, A. Raevska, V. F. Sopin, A. I. Kuklin, and F. Kh. Islamov, Zhidkie kristally i ikh prakticheskoe ispol'zovanie [Liquid Crystals and Their Practical Applications], IvGU, Ivanovo, 2002, no. 2, 54 (in Russian).
S. De, V. K. Aswal, P. S. Goyal, and S. Bhattacharya, J. Phys. Chem. B, 1997, 101, 5639.
A. T Gubaidullin, I. L. Nikolaeva, D. I. Kharitonov, I. A. Litvinov, N. I. Bashmakova, A. R. Burilov, M. A. Pudovik, and A. I. Konovalov, Zh. Obshch. Khim., 2002, 72, 280 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)]. Received May 26, 2003; in revised form September 3, 2003
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Ryzhkina, I.S., Pashirova, T.N., Filippova et al. Aggregation behavior and catalytic activity of systems based on calix[4]resorcinarene derivatives and surfactants. 1. Mixed micellization of aminomethylated calix[4]resorcinarenes with cetyltrimethylammonium bromide in aqueous dimethylformamide. Russian Chemical Bulletin 53, 1520–1527 (2004). https://doi.org/10.1023/B:RUCB.0000046250.42162.36
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DOI: https://doi.org/10.1023/B:RUCB.0000046250.42162.36