Self-Aggregation and Solubilizing Properties of the Supramolecular System Based on Azobenzenesulfonate Calix[4]arene and CTAB

Ruslan R. Kashapov,^a@ Alina M. Bekmukhametova,^a Lucia Ya. Zakharova,^aZaliya V. Akhmetzyanova,^b Elena V. Popova,^a Svetlana E. Solovieva,^a,bIgor S. Antipin,^a,b and Alexander I. Konovalov^a

^aA.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, Russian Federation

^bKazan Federal University, 420008 Kazan, Russian Federation

^@Corresponding author E-mail: kashapov@iopc.ru

DOI: 10.6060/mhc171146k

Macroheterocycles 2017 10(4-5) 454-459

The intermolecular interaction of azobenzenesulfonate calix[4]arene with cationic surfactant CTAB was studied by a complex of physicochemical methods. The influence of calix[4]arene:CTAB ratio on the form of the aggregates in their mixed composition in the aqueous medium was determined. Single-layer vesicles are formed in the equimolar azobenzenesulfonate calix[4]arene-CTAB mixture. A threefold increase in the proportion of CTAB leads to the enlargement of vesicles, namely, an increase in numbers of bilayers. Spectrophotometry was used to select the conditions for binding of the hydrophobic spectral probe Sudan I by this mixed composition. The fluorescence spectroscopy establishes dependence between the amount of encapsulated Rhodamine B and the size of the vesicle. Thus, the azobenzenesulfonate calix[4]arene–CTAB system is capable for binding of both hydrophobic and hydrophilic substrates depending on the components ratio..

References:

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1. Schneider H.J. Applications of Supramolecular Chemistry. Boca Raton: CRC Press, 2012. 453 p.

2. Hermans T.M., Broeren M.A.C., Gomopoulos N., Smeijers A.F., Mezari B., Van Leeuwen E.N.M., Vos M.R.J., Magusin P.C.M.M., Hilbers P.A.J., Van Genderen M.H.P., Sommerdijk N.A.J.M., Fytas G., Meijer E.W. J. Am. Chem. Soc. 2007, 129, 15631–15638.
https://doi.org/10.1021/ja074991t

3. Gohy J.F., Lohmeijer B.G.G., Varshney S.K., Schubert U.S. Macromolecules 2002, 35, 4560–4563.
https://doi.org/10.1021/ma012042t

4. Kabanov A.V., Bronich T.K., Kabanov V.A., Yu K., Eisenberg A. J. Am. Chem. Soc. 1998, 120, 9941–9942.
https://doi.org/10.1021/ja981922t

5. Han Y., Wang W., Tang Y., Zhang S., Li Z., Wang Y. Langmuir 2013, 30, 9316–9323.
https://doi.org/10.1021/la4019713

6. Kumar M., George S.J. Chem. Asian J. 2014, 9, 2427–2431.
https://doi.org/10.1002/asia.201402426

7. Zhang X., Chen Zh., Würthner F. J. Am. Chem. Soc. 2007, 129, 4886–4887.
https://doi.org/10.1021/ja070994u

8. Bojinova T., Coppel Y., Lauth-de Viguerie N., Milius A., Rico-Lattes I., Lattes A. Langmuir 2003, 19, 5233–5239.
https://doi.org/10.1021/la030030q

9. Kim K.T., Meeuwissen S.A., Noltea R.J.M., van Hest J.C.M. Nanoscale 2010, 2, 844–858.
https://doi.org/10.1039/b9nr00409b

10. Wang Y., Ma N., Wang Zh., Zhang X. Angew. Chem. Int. Ed. 2007, 46, 2823–2826.
https://doi.org/10.1002/anie.200604982

11. Zhang H., Sun L., Liu Zh., An W., Hao A., Xin F., Shen J. Colloids Surf., A 2010, 358, 115–121.
https://doi.org/10.1016/j.colsurfa.2010.01.026

12. Sun T., Li Yu., Zhang H., Li J., Xin F., Kong L., Hao A. Colloids Surf., A 2011, 375, 87–96.
https://doi.org/10.1016/j.colsurfa.2010.11.067

13. Kashapov R.R., Pashirova T.N., Kharlamov S.V., Ziganshina A.Yu., Zhiltsova E.P., Lukashenko S.S., Zakharova L.Ya., Latypov S.K., Konovalov A.I. Phys. Chem. Chem. Phys. 2011, 13, 15891–15898.
https://doi.org/10.1039/c1cp20906j

14. Kharlamov S.V., Kashapov R.R., Pashirova T.N., Zhiltsova E.P., Ziganshina A.Yu., Zakharova L.Ya., Latypov Sh.K., Konovalov A.I. J. Phys. Chem. C 2013, 117, 20280–20288.
https://doi.org/10.1021/jp406643g

15. Wang K., Guo D.S., Wang X., Liu Y. ACS Nano 2011, 5, 2880–2894.
https://doi.org/10.1021/nn1034873

16. Zakharova L.Ya., Konovalov A.I. Colloid J. 2012, 74, 194–206.
https://doi.org/10.1134/S1061933X12020147

17. Francisco V., BasilioN., Garcia-Rio L., Leis J.R., Maques E.F., Vazquez-Vazquez C. Chem. Commun. 2010, 46, 6551–6553.
https://doi.org/10.1039/c0cc01806f

18. Basilio N., Martín-Pastor M., García-Río L. Langmuir 2012, 28, 6561−6568.
https://doi.org/10.1021/la3006794

19. Zhiltsova E.P., Kashapov R.R., Zakharova L.Ya., Lukashenko S.S., Timosheva A.P., Kasymova E.M., Kayupov A.R., Burilov A.R. Kinet. Catal. 2012, 53, 231–238.
https://doi.org/10.1134/S0023158412020176

20. Kashapov R.R., Pashirova T.N., Zhiltsova E.P., Lukashenko S.S., Ziganshina A.Yu, Zakharova L.Ya. Russ. J. Phys. Chem. A 2012, 86, 200–204.
https://doi.org/10.1134/S003602441201013X

21. Gaynanova G.A., Bekmukhametova A.M., Sayfutdinova M.N., Gavrilova E.L., Zakharova L.Ya., Sinyashin O.G. Russ. Chem. Bull. 2015, 8, 1982–1985.
https://doi.org/10.1007/s11172-015-1105-1

22. Gaynanova G.A., Bekmukhametova A.M., Kashapov R.R., Ziganshina A.Yu., Zakharova L.Ya. Chem. Phys. Lett. 2016, 652, 190–194.
https://doi.org/10.1016/j.cplett.2016.04.021

23. Oshima T., Oishi K., Ohto K., Inoue K. J. Inclusion Phenom. Macrocyclic Chem. 2006, 55, 79–85.
https://doi.org/10.1007/s10847-005-9022-9

24. Menon Sh.K., Patel R.V., Panchal J.G. J. Inclusion Phenom. Macrocyclic Chem. 2010, 67, 73–79.
https://doi.org/10.1007/s10847-009-9674-y

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Self-Aggregation and Solubilizing Properties of the Supramolecular System Based on Azobenzenesulfonate Calix[4]arene and CTAB

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