Aggregation behavior and catalytic activity of systems based on calix[4]resorcinarene derivatives and surfactants. 1. Mixed micellization of aminomethylated calix[4]resorcinarenes with cetyltrimethylammonium bromide in aqueous dimethylformamide

Рыжкина, И. С.; Pashirova, Tatiana N.; Filippova, Ya. A.; Kudryavtseva, L. A.; Timosheva, A. P.; Архипов, В. П.; Idiyatullin, Z. Sh.; Попова, Е. В.; Burilov, A. R.; Коновалов, А. И.

doi:10.1023/b:rucb.0000046250.42162.36

Cited by 8 publications

(13 citation statements)

References 10 publications

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“…Measurements of surface tension (σ) of aqueous solutions of calixarenes showed that calix [4]resorcinarene 2 possesses the best of surface-active properties (see Table 1). The solutions of p-sulfonated calix[n]arenes 3 and 4 have very close σ values.…”

Section: Resultsmentioning

confidence: 99%

“…Raw SWNT materials contained 15-20% of nanotubes (diameter distribution was 1.46 nm ± 0.15 nm) and were not pre-purified [7]. The following calixarenes were used in this work: сalix [4]resorcinarene aminomethylated on the lower rim (1) [8], phosphorylated aminomethylated calix [4]resorcinarene (2) [4], p-sulfonatocalix [4]arene modified by butyl substituents (3) [6] and p-sulfonato-calix [6]arene modified by dodecyl substituents (4) [6]. Chemical structures of calixarenes 1-4 are shown in Fig.…”

Section: Methodsmentioning

confidence: 99%

“…A hydrophobic cavity in calixarene molecule substantially changes and complicates the mode of formation of micelles and intermolecular complexes as compared to common surfactants. Calixarenes can trap substrate (guest) not only in their own cavities to form inclusion complexes but also in the core of their micelles [4][5][6]. We have found that micellar solutions of calix [4]resorcinarene derivatives and p-sulfonato-calix[n]arenes (n = 4, 6) modified by alkyl (butyl and dodecyl) substituents form stable dispersion of individual nanotubes at calixarene concentrations lower than those of common surfactants.…”

Section: Introductionmentioning

confidence: 98%

“…Calixarenes can trap substrate (guest) not only in their own cavities to form inclusion complexes but also in the core of their micelles [4][5][6]. We have found that micellar solutions of calix [4]resorcinarene derivatives and p-sulfonato-calix[n]arenes (n = 4, 6) modified by alkyl (butyl and dodecyl) substituents form stable dispersion of individual nanotubes at calixarene concentrations lower than those of common surfactants. Solubilization of SWNT in aqueous solutions of calixarenes has successively been characterized using UV-vis-NIR spectroscopy.…”

Section: Introductionmentioning

confidence: 98%

“…The present work reports the investigations of solubilization of pristine SWNT in aqueous micellar solutions of various types functionalized amphiphilic macrocyclic compounds, namely, calix [4]resorcinarene derivatives and p-sulfonato-calix[n]arenes (n = 4, 6) modified by alkyl (butyl and dodecyl) substituents. Calixarenes appear as molecular platfroms suitable for the design of related three-dimensional structures with assistance of cavities essentially differing in size.…”

Section: Introductionmentioning

confidence: 99%

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Solubilization of single‐wall carbon nanotubes in aqueous solutions of calixarenes

Лобач

Рыжкина

Spitsina

et al. 2007

Physica Status Solidi (b)

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The present work reports the studies of the solubilization of single-wall carbon nanotubes in aqueous solutions of calix[4]resorcinarene derivatives and p-sulfonato-calix[n]arenes (n = 4, 6) modified by alkyl (butyl and dodecyl) substituents. The highest dispersion ability is demonstrated by calix[4]resocinarene, which bears aminomethyl groups on the upper rim and phosphorus-bearing alkyl fragments on the lower rim of calixarene. Optical absorption spectroscopy justifies the formation of stable suspensions of SWNT in aqueous solutions of calixarenes.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Solubilization of single‐wall carbon nanotubes in aqueous solutions of calixarenes

Лобач

Рыжкина

Spitsina

et al. 2007

Physica Status Solidi (b)

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Supramolecular systems of amphiphilic derivatives of calix[4]resorcinarenes and surfactants in chloroform

Рыжкина

Timosheva²,

Чернова³

et al. 2007

Russ Chem Bull

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Aggregation of amphiphilic calix[4]resorcinarenes (CRA) modified by carboxymethyl (1), 2 hydroxyethyl (2), methylamino acetal (3), and aminomethyl (4) fragments and their interac tion with some synthetic (5, 6) and natural (7, 8) surfactants in the low polarity solvent (chloroform) were studied by permittivity measurements and FT IR spectroscopy. Com pounds 1-4 and surfactants form aggregates at critical micelle concentrations (CMC) of 2.0, respectively. The CMC values of CRA-surfactant mixed aggregates depend on the surfactant structure and the structure and concentration of CRA. Analysis of the IR spectra of solutions of a series of amphiphilic CRA (2-4, 9, 10) and their mixtures with the cationic surfactant N cetyl N,N dimethyl N (2 hydroxyethyl)ammonium bromide (5) showed that an increase in the concentration of the solutions in individual and mixed systems is accompanied by a decrease in the molar integral intensities and intensities in the maxima of the absorption bands of the О-Н and С-Н bonds down to the CMC point, after which these values change slightly. The discovered effect, which is differently pronounced for all systems studied, indicates that both the polar "head" groups and nonpolar fragments of CRA and surfactant are involved in the formation of supramolecules of the reverse micelle type in all cases.Synthetically available calixarenes are the organized in a complicated manner three dimensional macrocyclic phenols that are able to form with ions and neutral mol ecules supramolecular aggregates modeling functions of complex biomolecules, for instance, transport 1 or cata lytic 2 functions. We have earlier 3,4 shown that amphiphilic aminomethylated calix[4]resorcinarenes (CRA) in aque ous and organic media are micelle forming surfac tants. These compounds can react with synthetic surfac tants, such as cetyltrimethylammonium bromide and Triton X 100, to form mixed supramolecular aggregates with high catalytic activity in hydrolysis of p nitrophenyl esters of phosphorus acids. 5-7 Interest in processes of self organization in solutions of surfactant mixtures 8 and compounds of complicated molecular architecture has recently increased considerably 1,9,10 primarily due to steady demands of modern nano and biotechnologies for new polyfunctional reagents. Therefore, studies of aggre gation of new amphiphilic derivatives of calix[4]resorcin arene and their interaction with synthetic and natural surfactants seems very urgent.The purpose of the present work is to study the aggre gation of a series of amphiphilic CRA modified by carboxymethyl (1), 2 hydroxyethyl (2), methylamino acetal (3), and aminomethyl (4) fragments in the absence and presence of synthetic surfactants (N cetyl N,N di methyl N (2 hydroxyethyl)ammonium bromide (5), Triton X 100 (6)) and natural membrane lipids (phospha tidylcholine (7), sodium deoxycholate (8)) in a medium of the low polarity solvent (chloroform). Permittivity measurements and FT IR spectroscopy served as methods of investigation. The influence of the structure and con cen...

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Supramolecular systems based on the melamine salt of bis(hydroxymethyl)phosphinic acid (melafen) dihydrate and surfactants

et al. 2008

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Bis(hydroxymethyl)phosphinic acid and melamine were shown by FTIR and UV spectroscopy to form the salt (melafen), whose cations and anions involving water molecules can be joined into supramolecular structures due to electrostatic interactions and hydrogen bonds. The conductometry, dielcometric titration, and dynamic light scattering methods showed that melafen in water and chloroform in a concentration range of 10 -10 -10 -4 mol L -1 involving the solvent structures exist as supramolecular polymeric nanostructures, whose size and properties change nonlinearly depending on the melafen concentration.The melamine salt of bis(hydroxymethyl)phosphinic acid dihydrate (melafen, 1) is an efficient regulator of plant growth and development, which is of considerable interest for practical use in agriculture and biotech nology. 1,2a The studies of the influence of compound 1 on the growth and energy processes in the living cell 3 and on the physicochemical state of biological membranes of various origin, 4 as well as the investigation of the mecha nism of action of the compound on the regulation of the plant cell metabolism 2b revealed that melafen is highly physiologically active at low concentrations, which are classified as low and superlow doses of biologically active substances. 5,6 The existing hypotheses for the mechanism of action of the superlow doses cannot completely explain the nature of this widespread phenomenon. 5,6 Therefore, the broad study of the effect of biologically active sub stances of the melafen type on systems of different levels of complexity and organization, namely, from supramo lecular systems modeling functions of biomolecules to complicated biological objects, seems especially urgent.Our first report is devoted to the study of the structure of melafen and its self association in aqueous and organic (chloroform) media. The interaction of melafen with surfactants of different nature and their micellar aggre gates modeling the components and surface layer of bio logical membranes will be discussed elsewhere. ExperimentalMelafen (1) was synthesized according to an earlier described procedure. 1 The association of compound 1, bis(hydroxymethyl) phosphinic acid (BPA), and melamine (M) in chloroform was studied by dielcometric titration, during which the concentration dependences of the dielectric permittivity (ε) were obtained and analyzed. 7-10 The dielectric permittivities of a series of solutions were determined on a setup consisting of an E12 I instrument operating in the beat mode and a measuring cell, being a tempera ture controlled condenser. Chloroform was purified using a stan dard method. 11 The estimation of the residual water content carried out by FTIR spectroscopy showed that the chloroform samples used contained ~0.1 wt.% water. The association of compound 1, BPA, and M in water was studied by the conductometric method, measur ing the change in the electric conductivity (χ) of the solutions at 25 °С (inoLab Cond Level 1 conductometer, relative measurement error 0.5%). Water and solu...

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Aggregation behavior and catalytic activity of systems based on calix[4]resorcinarene derivatives and surfactants. 1. Mixed micellization of aminomethylated calix[4]resorcinarenes with cetyltrimethylammonium bromide in aqueous dimethylformamide

Cited by 8 publications

References 10 publications

Solubilization of single‐wall carbon nanotubes in aqueous solutions of calixarenes

Solubilization of single‐wall carbon nanotubes in aqueous solutions of calixarenes

Supramolecular systems of amphiphilic derivatives of calix[4]resorcinarenes and surfactants in chloroform

Supramolecular systems based on the melamine salt of bis(hydroxymethyl)phosphinic acid (melafen) dihydrate and surfactants

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