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Amino Acid‐Functionalized Calix[4]Resorcinarene Solubilization by Mono‐ and Dicationic Surfactants
Author(s) -
Zakharova Lucia Ya.,
Serdyuk Anna A.,
Mirgorodskaya Alla B.,
Kapitanov Illia V.,
Gainanova Gulnara A.,
Karpichev Yevgen,
Gavrilova Elena L.,
Sinyashin Oleg G.
Publication year - 2016
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-016-1792-0
Subject(s) - resorcinarene , chemistry , micelle , pulmonary surfactant , calixarene , bromide , ammonium bromide , polymer chemistry , substituent , organic chemistry , aqueous solution , molecule , biochemistry
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.