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Amino Acid-Functionalized Calix[4]Resorcinarene Solubilization by Mono- and Dicationic Surfactants

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Journal of Surfactants and Detergents

Abstract

Poorly water-soluble calix[4]resorcinarenes modified with amino acid (Ala, Val) at the upper rim formed a water-soluble mixed system with micelles of monocationic surfactants cetyltrimethylammonium bromide, cetyldimethyl(2-hydroxyethyl)ammonium bromide, and dicationic (gemini) surfactants, alkanediyl-α,ω-bis(dimethyltetradecylammonium bromides (14-s-14, where s = 2, 4, or 6). UV–Vis and DLS methods demonstrated that the micellar systems of surfactant/functionalized calix[4]resorcinarene underwent structural changes within a relatively narrow concentration range followed by changes in solubilization capacity and polydispersity. Gemini surfactants and monocationic/gemini mixed surfactant systems were provided selectivity in their interaction with calix[4]resorcinarene depending on the bulkiness of the substituent at the upper rim of calix[4]resorcinarene, gemini surfactant spacer length, and mixed micelles. These systems represent a direction to create biocompatible water-soluble functionalized calix[4]resorcinarene composition and may open perspectives in designing organized systems with controllable properties.

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Acknowledgments

The authors acknowledge the grant of the Russian Foundation for Basic Research (RFBR) 14-03-90409_Ukr. AS thanks the RFBR for Visiting Research Grant #15-33-50179. YK thanks excellence project of Faculty of Informatics and Management, University of Hradec Kralove and FNHK for supporting this research.

Author information

Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 420088, Kazan, Russian Federation

    Lucia Ya. Zakharova, Alla B. Mirgorodskaya, Gulnara A. Gainanova & Oleg G. Sinyashin

  2. Kazan National Research Technological University, 420015, Kazan, Russian Federation

    Lucia Ya. Zakharova, Alla B. Mirgorodskaya, Gulnara A. Gainanova, Elena L. Gavrilova & Oleg G. Sinyashin

  3. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02660, Kiev, Ukraine

    Anna A. Serdyuk & Illia V. Kapitanov

  4. L.M. Litvinenko Institute of Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 02160, Kiev, Ukraine

    Anna A. Serdyuk & Illia V. Kapitanov

  5. Center for Basic and Advanced Research, Faculty of Informatics and Management, University of Hradec Kralove, 50002, Hradec Kralove, Czech Republic

    Yevgen Karpichev

  6. Department of Chemistry, Tallinn University of Technology, 12618, Tallinn, Estonia

    Yevgen Karpichev

Authors
  1. Lucia Ya. Zakharova
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  2. Anna A. Serdyuk
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  3. Alla B. Mirgorodskaya
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  4. Illia V. Kapitanov
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  5. Gulnara A. Gainanova
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  6. Yevgen Karpichev
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  7. Elena L. Gavrilova
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  8. Oleg G. Sinyashin
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Corresponding author

Correspondence to Yevgen Karpichev.

Electronic supplementary material

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11743_2016_1792_MOESM1_ESM.doc

Absorbance of saturated solution of studied calix[4]resorcinarene as a function of concentration of surfactant are available as Figs. S1 to S6; the tabular summary is available as Table S1 (DOC 56 kb)

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Zakharova, L.Y., Serdyuk, A.A., Mirgorodskaya, A.B. et al. Amino Acid-Functionalized Calix[4]Resorcinarene Solubilization by Mono- and Dicationic Surfactants. J Surfact Deterg 19, 493–499 (2016). https://doi.org/10.1007/s11743-016-1792-0

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  • DOI: https://doi.org/10.1007/s11743-016-1792-0

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