A Supramolecular Amphiphile Based on Calix[4]resorcinarene and Cationic Surfactant for Controlled Self-Assembly

Abstract

A novel supramolecular system based on calix[4]resorcinarene sulfonatoalkylated at the lower rim and piperidine-methylated at the upper rim and the cationic surfactant hexadecyl-1-azonia-4-azobicyclo[2.2.2]octane bromide was investigated by methods of NMR, tensiometry, conductometry, potentiometry, dynamic light scattering, X-ray powder diffraction, and spectral probe techniques. Both types of molecules were found to self-associate in aqueous solution, with aggregates of different morphology formed. Importantly, a supramolecular amphiphilic binary system with controlled structure and binding behavior could be fabricated. At high surfactant concentration, the formation of its own aggregates takes place. In the systems with the excess of cyclophane the supramolecular amphiphiles are formed, which, in turn, self-assemble in particles with a large hydrophobic core. Thereby the structure of supramolecular species is determined by relative fractions of components and, hence, could be selectively controlled. The found properties can be used for the design of nanocontainers with the controlled cavity size.

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

“…The use of calixarenes and surfactants [13,14,[16][17][18][19][20][21][22] in the creation of superamphiphiles is of particular interest. It is known that macrocycles, thanks to the presence of a molecular cavity and the preorganization of functional groups, are able to participate in guest-host interactions.…”

“…On the other hand, interest in macrocycles is due to the specific geometry of their molecules, which is important in the design of drug delivery systems and the development of antiviral drugs. [18][19][20] In the process of formation of mixed surfactant-calixarene compositions one can observe: (1) the increase in the solubility of macrocyclic compounds; [23] (2) the activation of binding processes of hydrophobic and hydrophilic substrates by monitoring the morphology of mixed aggregates; [13][14][15] (3) the decrease in the critical aggregation concentration. [13] The non-toxicity of calixarenes and surfactants makes them attractive for constructing receptors and carriers in solving biotechnological problems.…”

Aggregation and Solubilization Properties of System Based on Glycine-Calix[4]resorcinol and Sodium Dodecyl Sulfate in Aqueous Medium

“…[1][2][3][4][5][6] The formation of these mixed compositions can reduce the consumption of reagents [1,7] and connect the factors of morphology control of functional aggregates. [8][9][10] A review of the literature shows that in recent years a significant number of calix [4]resorcinol derivatives have been synthesized, and their aggregation properties in the absence and in the presence of surfactants have been studied. [8][9][10][11][12][13][14] Despite the fact that surfactants in this case can play the role of a matrix facilitating the processes of self-aggregation, the mixed surfactant systems with calixarene containing biocompatible fragments are much less studied.…”

“…[8][9][10] A review of the literature shows that in recent years a significant number of calix [4]resorcinol derivatives have been synthesized, and their aggregation properties in the absence and in the presence of surfactants have been studied. [8][9][10][11][12][13][14] Despite the fact that surfactants in this case can play the role of a matrix facilitating the processes of self-aggregation, the mixed surfactant systems with calixarene containing biocompatible fragments are much less studied. Aggregation of surfactants in the presence of calixarenes containing amino acid groups has not been studied at all.…”

Aggregation in a Binary System Based on Calix[4]resorcinol with Phosphonium Groups and Hydrophilic Polymers

“…[1][2][3][4][5][6] Формирование смешан-ных композиций на основе вышеперечисленных строи-тельных блоков способно снизить расход реагентов [1,7] и подключить факторы управления морфологией агре-гатов. [8][9][10][11] Бинарные композиции на основе поверхност-но-активных веществ (ПАВ), [12] полимер-коллоидные комплексы [7] и системы ПАВ-каликсарен [8][9][10] неизменно оказываются в фокусе научных исследований. Однако смешанные системы каликсарен-полимер гораздо менее исследованы, [13,14] несмотря на то что полимеры в данном случае могут играть роль матрицы, облегчая процессы самоорганизации.…”