Abstract
The aggregation of octa-2-hydroxyethylated calix[4]resorcines (CR) with different alkyl chain length (R = Et, n-C5H11, n-C11H23), hydrophobically modified polyethyleneimine (HPEI) and their mixed systems was investigated by the tensiometry and dynamic light scattering in water and water-organic solvents at different temperatures. The critical aggregation concentration (CAC) and the size of aggregates were determined. It was established that the temperature affects significantly the surface and aggregation properties of the CR. The hydrolysis of 4-nitrophenyl-О-butylchloromethyl phosphonate was investigated in the presence of CR, HPEI, and their mixed systems by spectrophotometry. The parameters of the reaction (rate constant in the micellar phase, binding constant of the substrate with aggregates, and CAC) testify that the catalytic activity of the HPEI system in the presence of СR with undecyl radicals is the highest.
Similar content being viewed by others
References
K. C. Tam, E. Wyn-Jones, Chem. Soc. Rev., 2006, 35, 693.
M. Fechner, J. Koetz, Langmuir, 2013, 29, 7600.
A. Parmara, S. Chavda, P. Bahadur, Colloids Surf. A, 2014, 441, 389.
A. Bhakay, M. Azad, E. Bilgili, R. Dave, Int. J. Pharm., 2014, 461, 367.
D. R. Gabdrakhmanov, D. Samarkina, F. G. Valeeva, L. F. Saifina, V. E. Semenov, V. S. Reznik, L. Ya. Zakharova, A. I. Konovalov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 573 [Izv. Akad. Nauk, Ser. Khim., 2015, 573].
T. N. Pashirova, E. P. Zhil´tsova, S. S. Lukashenko, L. Ya. Zakharova, A. I. Konovalov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 2879 [Izv. Akad. Nauk, Ser. Khim., 2015, 2879].
S. Dong, B. Zheng, F. Wang, F. Huang, Acc. Chem. Res., 2014, 47, 1982.
X. Ma, H. Tian, Acc. Chem. Res., 2014, 47, 1971.
A. Toutianoush, J. Schnepf, A. E. Hashani, B. Tieke, Adv. Funct. Mater., 2005, 4, 700.
M. Y. Lee, H. J. Kim, G. Y. Jung, A. R. Han, S. K. Kwak, B. J. Kim, J. H. Oh., Adv. Mater., 2015, 27, 1540.
T. Zhou, N. Song, H. Yu, Y.-W. Yang, Langmuir, 2015, 31, 1454.
L. Zakharova, Y. Kudryashova, A. Ibragimova, E. Vasilieva, F. Valeeva, E. Popova, S. Solovieva, I. Antipin, Y. Ganeeva, T. Yusupova, A. Konovalov, Chem. Eng. J., 2012, 185–186, 285.
R. E. McGovern, A. A. McCarthy, P. B. Crowley, Chem. Commun., 2014, 50, 10412.
H. Altshulera, O. Altshuler, Eur. J. Chem., 2011, 2, 14.
D. S. Guo, T. X. Zhang, Y. X. Wang, Y. Liu, Chem. Commun., 2013, 49, 6779.
E. Ozyilmaz, S. Sayin, Appl. Biochem. Biotechnol., 2013, 170, 1871.
A. B. Mirgorodskaya, E. I. Yackevich, Y. R. Kudryashova, R. R. Kashapov, S. E. Solovieva, A. T. Gubaidullin, I. S. Antipin, L. Y. Zakharova, A. I. Konovalov, Colloids Surf. B., 2014, 117, 497.
L. Ya. Zakharova, V. V. Syakaev, M. A. Voronin, F. V. Valeeva, A. R. Ibragimova, Yu. R. Ablakova, E. Kh. Kazakova, Sh. K. Latypov, A. I. Konovalov, J. Phys. Chem., 2009, 113, 6182.
T. N. Pashirova, S. S. Lukashenko, E. M. Kosacheva, M. V. Leonova, I. R. Knyazeva, A. R. Burilov, L. A. Kudryavtseva, A. I. Konovalov, Colloid. J. (Engl. Transl.), 2008, 70, 202 [Kolloid. Zhurn., 2008, 70, 227].
T. N. Pashirova, E. M. Gibadullina, A. R. Burilov, R. R. Kashapov, E. P. Zhiltsova, V. V. Syakaev, W. D. Habicher, M. H. Rümmeli, S. K. Latypov, A. I. Konovalov, L. Y. Zakharova, RSC Adv., 2014, 4, 9912.
F. M. Menger, L. H. Gan, E. Johnson, D. H. Durst, J. Am. Chem. Soc., 1987, 109, 2800.
G. A. Gaynanova, A. R. Valiakhmetova, D. A. Kuryashov, Yu. R. Kudryashova, S. S. Lukashenko, V. V. Syakaev, Sh. K. Latypov, S. V. Bukharov, N. Yu. Bashkirtseva, L. Ya. Zakharova, Chem. Phys. Lett., 2013, 588, 145.
A. Arcelli, C. Concilio, J. Org. Chem., 1996, 61, 1682.
A. Arcelli, C. Concilio, J. Chem. Soc., 1983, 1327.
US Patent 2922810, 1960; Chem. Abstr., 1960, 54, 9848.
V. E. Bel´skii, L. A. Kudryavtseva, O. M. Il´ina, B. E. Ivanov, J. Gen. Chem. USSR (Engl. Transl.), 1979, 49, 2470 [Zh. Obshch. Khim., 1979, 49, 2470].
E. Fendler, Dzh. Fendler, Catalysis in Micellar and Mаcromolecular Systems, Acad. Press, New York, 1975, 545 pp.
T. N. Pashirova, E. P. Zhil´tsova, S. S. Lukashenko, L. Ya. Zakharova, A. I. Konovalov, Russ. J. Struct. Chem. (Engl. Transl.), 2014, 55, 1541 [Zh. Structur. Khim., 2014, 55, 362].
A. Rodrýguez, M. Graciani, M. L. Moya, Langmuir, 2008, 24, 12785.
Kabir-ud-Din, P. A. Koya, J. Chem. Eng. Data, 2010, 55, 1921.
D. J. F. Taylor, R. K. Thomas, J. Penfold, Adv. Colloid. Interface Sci., 2007, 132, 69.
L. Ya. Zakharova, A. R. Ibragimova, F. G. Valeeva, A. V. Zakharov, A. R. Mustafina, L. A. Kudryavtseva, H. E. Harlampidi, A. I. Konovalov, Langmuir, 2007, 23, 3214.
G. A. Gaynanova, G. I. Vagapova, F. G. Valeeva, E. A. Vasilieva, I. V. Galkina, L. Ya. Zakharova, O. G. Sinyashin, Colloid Surf. A, 2016, 489, 95.
H. Kise, A. Hayakawa, H. Noritomi, J. Biotechnol., 1990, 14, 239.
V. V. Mozhaev, Y. L. Khmelnitsky, M. V. Sergeeva, A. B. Belova, N. L. Klyachko, A. V. Levashov, K. Martinek, Eur. J. Biochem., 1989, 184, 597.
L. Faller, J. M. Sturtevant, J. Biol. Chem., 1966, 241, 4825.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences O. G. Sinyashin on the occasion of his 60th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1272–1277, May, 2016.
Rights and permissions
About this article
Cite this article
Pashirova, T.N., Zhil´tsova, E.P., Lukashenko, S.S. et al. Supramolecular systems based on polyethyleneimines and octa-2-hydroxyethylated calix[4]resorcinarenes. Aggregation and catalytic activity. Russ Chem Bull 65, 1272–1277 (2016). https://doi.org/10.1007/s11172-016-1447-3
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-016-1447-3