Effect of structure of tetramethyl sulfonated calix[4]resorcinarene aggregates on paraquat redox reactions

Shalaeva, Yana V.; Yanilkin, V. V.; Morozova, Julia E.; Kazakova, E. Kh.; Syakaev, Victor V.; Макарова, Н. А.; Morozov, V. V.; Коновалов, А. И.

doi:10.1134/s1061933x10020171

Cited by 8 publications

(6 citation statements)

References 30 publications

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“…The theoretical hydrodynamic radii were calcu lated employing the HYDRONMR software package [32]. The macrocycle structures used in the calcula tions were optimized by the molecular mechanics method (MM2) employing the Chem3D software package [33]. Dynamic light scattering (DLS) by samples pre liminarily cleared of dust by filtration was measured with a Photocor Complex photon correlation spec trometer (Photocor Instruments, United States).…”

Section: Methodsmentioning

confidence: 99%

Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

et al. 2012

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NMR methods are employed to study the effects of inorganic salts, solvents, and guest molecules of methylviologen (MV 2+ ) and choline (Ch + ) on the aggregation properties of water soluble tetramethylene sulfonate substituted calix[4]resorcinarenes containing methyl (1), amyl (2), and heptyl (3) substituents in the lower rim. It is established that, in aqueous solutions at concentrations of 1-10 mM, compound 1 exists in the monomeric form; the size of aggregates of amphiphilic compound 2 gradually increases (aggregation number varies from 1 to 20); and hydrophobic compound 3 dissolves only in slightly alkaline aqueous solu tions to form large micellar aggregates. For macrocycles 2 and 3, which are inclined to aggregation, the aggre gate sizes depend on the concentration, pH, and ionic strength of solutions, as well as on the presence of organic solvents. Macrocycle 1 binds guest molecules Ch + and MV 2+ to yield inclusion complexes. In the presence of aggregates of substance 2, the binding of guest molecules is more efficient and they are encapsu lated between the rim of one molecule and the tail of another molecule of compound 2. The presence of guest molecules enhances the aggregation of macrocycle 2. In the case of compound 3 solutions, guest Ch + mole cules are predominantly localized in the hydrophobic environment of alkyl substituents of the host.

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Section: Methodsmentioning

confidence: 99%

Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

et al. 2012

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“…[19][20][21][22][23][24][25] Anionic organic macrocycles and cages with anionic groups such as carboxylate [26,27] and sulfonate groups [28][29][30][31][32] have also been reported. However,t hese anionic groups are not weakly coordinating.…”

Section: Distinctiveness Of M-wcasmentioning

confidence: 99%

“…Numerous organic macrocycles, nanocapsules, and nanoporous cages have been reported in the literature, however, the large majority of them are charge‐neutral 19–25. Anionic organic macrocycles and cages with anionic groups such as carboxylate26, 27 and sulfonate groups28–32 have also been reported. However, these anionic groups are not weakly coordinating.…”

Section: Distinctiveness Of M‐wcasmentioning

confidence: 99%

Macrocyclic Weakly Coordinating Anions

Landskron

2015

Chemistry A European J

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Herein, the concept of macrocyclic weakly coordinating anions (M-WCAs) is introduced. Synthetic methodologies are described how to access M-WCAs by thermodynamically controlled self-assembly in high yields, in particular through condensation and alkyne metathesis reactions. The anticipated properties and applications of M-WCAs in solid state and in solution are discussed, specifically for gas storage and separation, homogeneous and heterogeneous catalysis, and as liquid and solid electrolytes.

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“…In 10 mM solution, aggregates of SCA2 have head-to-tail packing subunits due to interactions between the substituents of the upper and lower rims of two neighbor molecules with a number of aggregation of 20 . Tetraanion macrocycles SCA1 and SCA2 form host−guest complexes with both organic cations ( N -methylpyridinium, tetramethylammonium (TMA), methyl viologen, and promazine) and neutral molecules (xymedon and dimephosphone). It has been recently demonstrated that cation−radical or neutral species of methyl viologen are stabilized due to their encapsulation into head-to-tail subunits of SCA2 in the electrochemical redox process …”

Section: Introductionmentioning

confidence: 99%

“…Tetraanion macrocycles SCA1 and SCA2 form host−guest complexes with both organic cations ( N -methylpyridinium, tetramethylammonium (TMA), methyl viologen, and promazine) and neutral molecules (xymedon and dimephosphone). It has been recently demonstrated that cation−radical or neutral species of methyl viologen are stabilized due to their encapsulation into head-to-tail subunits of SCA2 in the electrochemical redox process …”

Section: Introductionmentioning

confidence: 99%

Investigation of Tetramethylenesulfonated Calix[4]resorcinarene Interactions with Azo Dyes in Aqueous Solution

et al. 2010

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The interaction of a macrocycle's aggregates with a guest molecule has special interest due to the double role, both of macrocycle cavity and self-associates, in the binding of the guests. Here, we report on the interactions of nonaggregated methyl-substituted (SCA1) and aggregated penthyl-substituted (SCA2) tetramethylenesulfonated calix[4]resorcinarenes with pH indicators methyl yellow (MY) and methyl orange (MO) in aqueous solutions. It was found that the pH of aqueous solutions of SCA1 and SCA2 depends on their concentration; besides, variation of the concentration of SCA1 and SCA2 results in a shift of the absorption maxima and of pH-sensitive azo dyes. Association of the marocycles with azo dyes was demonstrated to follow a proton-transfer mechanism accompanied by protonation of the dyes; it was found that excess of the macrocycle in solution with the universal buffer background shifts the pK(a) values and stabilizes the protonated form of the dyes. Consideration of interactions of small dye molecules with large molecular associates, containing both individual and multimolecule binding sites, gives a closer approximation of synthetic biomimetics to their natural prototypes.

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Effect of structure of tetramethyl sulfonated calix[4]resorcinarene aggregates on paraquat redox reactions

Cited by 8 publications

References 30 publications

Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

Macrocyclic Weakly Coordinating Anions

Investigation of Tetramethylenesulfonated Calix[4]resorcinarene Interactions with Azo Dyes in Aqueous Solution

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