Novel supramolecular system based on a cationic amphiphile bearing glucamine fragment: structural behavior and hydrophobic probe binding

Gabdrakhmanov, Dinar R.; Валеева, Ф. Г.; Syakaev, Victor V.; Лукашенко, С. С.; Захаров, С. В.; Kuryashov, D. A.; Bashkirtseva, N. Yu.; Zakharova, L. Ya.; Latypov, Shamil K.; Sinyashin, Оleg G.

doi:10.1016/j.mencom.2015.05.004

Cited by 13 publications

(8 citation statements)

References 28 publications

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“…Most probably, pyrene is incorporated into the hydrophobic region of the colloidal aggregates. Usually, the CMC values of surfactants determined by different methods are very similar [ 70 ]. But an additional binding of the fluorescent probe (pyrene) to the heterocyclic core of the isoindigo compounds cannot be excluded.…”

Section: Resultsmentioning

confidence: 99%

Nanoscale isoindigo-carriers: self-assembly and tunable properties

Pashirova

Богданов

Musin

et al. 2017

Beilstein J. Nanotechnol.

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Over the last decade isoindigo derivatives have attracted much attention due to their high potential in pharmacy and in the chemistry of materials. In addition, isoindigo derivatives can be modified to form supramolecular structures with tunable morphologies for the use in drug delivery. Amphiphilic long-chain dialkylated isoindigos have the ability to form stable solid nanoparticles via a simple nanoprecipitation technique. Their self-assembly was investigated using tensiometry, dynamic light scattering, spectrophotometry, and fluorometry. The critical association concentrations and aggregate sizes were measured. The hydrophilic–lipophilic balance of alkylated isoindigo derivatives strongly influences aggregate morphology. In the case of short-chain dialkylated isoindigo derivatives, supramolecular polymers of 200 to 700 nm were formed. For long-chain dialkylated isoindigo derivatives, micellar aggregates of 100 to 200 nm were observed. Using micellar surfactant water-soluble forms of monosubstituted 1-hexadecylisoindigo as well as 1,1′-dimethylisoindigo were prepared for the first time. The formation of mixed micellar structures of different types in micellar anionic surfactant solutions (sodium dodecyl sulfate) was determined. These findings are of practical importance and are of potential interest for the design of drug delivery systems and new nanomaterials.

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Section: Resultsmentioning

confidence: 99%

Nanoscale isoindigo-carriers: self-assembly and tunable properties

Pashirova

Богданов

Musin

et al. 2017

Beilstein J. Nanotechnol.

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“…N -Methylglucamine has been widely used for synthesizing new ionic liquids [ 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 ], always through a direct quaternization of the starting material. This reaction could be performed through a one-pot double alkylation [ 105 , 109 , 112 ], a two steps double alkylation [ 102 , 103 , 104 , 106 , 107 , 108 , 110 ], or a mono alkylation followed by a neutralization reaction [ 106 , 111 ]. The latter approach is very simple, does not require prior protection of the free hydroxyl groups, and therefore, has been used for preparing a variety of ILs.…”

Section: Synthesismentioning

confidence: 99%

“…Different starting materials have been employed for synthesizing carbohydrate-based surfactants ( d -galactose [ 28 ], d -gluconic acid [ 47 , 49 , 50 , 205 ], lactobionic acid [ 47 , 50 ], d -glucose [ 77 , 78 , 79 ], d -mannose [ 33 ], d -galactose [ 33 ], d -lactose [ 77 ], d -glucamine [ 102 , 111 ]), in all cases leading to final products containing a cationic nitrogen on the sugar moiety.…”

Section: Applicationsmentioning

confidence: 99%

“… No physical state reported. [ 109 ] 147 N -methyl- d -glucamine Solid 96–98 [ 102 ] 148 N -methyl- d -glucamine Not isolated [ 108 ] 149a N -methyl- d -glucamine No information (polymer) [ 107 ] 149b N -methyl- d -glucamine Classified as IL by the authors. No physical state reported.…”

Section: Table A1mentioning

confidence: 99%

“… Examples of ILs obtained starting from N -methylglucamine 145 [ 102 , 105 , 107 , 108 , 109 , 110 , 112 ]. …”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

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Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

2021

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Carbohydrates represent a promising option in transitioning from oil-based chemical resources to renewable ones, with the goal of developing chemistries for a sustainable future. Cellulose, hemicellulose, and largely available monosaccharides already provide useful chemical building blocks, so-called platform chemicals, such as levulinic acid and hydroxymethyl furfural, as well as solvents like cyrene or gamma-valerolactone. Therefore, there is great anticipation for novel applications involving materials and chemicals derived from sugars. In the field of ionic liquids (ILs), sugar-based ILs have been overlooked for a long time, mainly on account of their multistep demanding preparation. However, exploring new strategies for accessing sugar-based ILs, their study, and their exploitation, are attracting increasing interest. This is due to the growing concerns about the negative (eco)toxicity profile of most ILs in conjunction with their non-sustainable nature. In the present review, a literature survey concerning the development of sugar-based ILs since 2011 is presented. Their preparation strategies and thermal behavior analyses, sorted by sugar type, make up the first two sections with the intention to provide the reader with a useful guide. A final overview of the potential applications of sugar-based ILs and their future perspectives complement the present analysis.

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