Supramolecular Structures in the Presence of Ionic Liquids

Shen, Xinghai; Chen, Qingde; Zhang, Jingjing; Pei, Fei

doi:10.5772/15586

Cited by 6 publications

(8 citation statements)

References 345 publications

(330 reference statements)

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“…35 Benzo [21]crown-7 (BC7) is the smallest crown ether capable of forming pseudorotaxane structures with alkyl-substituted secondary ammonium ions (Scheme 2). 36 This recognition motif has been applied in the construction of elaborate supramolecular architectures.…”

Section: Gel-sol Transitions Induced By Molecular Recognitionmentioning

confidence: 99%

Self-recovering stimuli-responsive macrocycle-equipped supramolecular ionogels with unusual mechanical properties

Traulsen

Molina

et al. 2014

Org. Biomol. Chem.

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A chiral, crown-ether-functionalized bisurea gelator forms supramolecular gels in ionic liquids. The resulting ionogels show a remarkably high thermal stability with gel-sol transition temperatures (T gs ) reaching more than 100°C. The mechanical strength of these ionogels is surprisingly high and even comparable to that of cross-linked protein fibres. Furthermore, the ionogels exhibit rapid self-recovery properties after structural damage caused by deformation. Pseudorotaxanes form from the gelators' benzo[21]-crown-7 ethers as the wheels and secondary ammonium ions as the axles despite the competition between that cation and the imidazolium ions of the ionic liquid for crown ether binding. Pseudorotaxane formation as an external chemical stimulus triggers the gel-sol transition of the ionogels.

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Section: Gel-sol Transitions Induced By Molecular Recognitionmentioning

confidence: 99%

Self-recovering stimuli-responsive macrocycle-equipped supramolecular ionogels with unusual mechanical properties

Traulsen

Molina

et al. 2014

Org. Biomol. Chem.

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“…Moreover, the effect of FA-PILs on the physico-chemical properties of a non-ionic aqueous surfactant, such as d-α-Tocopherol polyethylene glycol succinate (vitamin E TPGS), has been evaluated. Indeed, it has been reported that surfactants are able to form various molecular aggregates in ILs [ 57 ], similar to micellization or liquid crystals’ formation in aqueous media.…”

Section: Introductionmentioning

confidence: 99%

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

et al. 2020

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For topical treatment of skin cancer, the design of pH-responsive nanocarriers able to selectively release the drug in the tumor acidic microenvironment represents a reliable option for targeted delivery. In this context, a series of newly synthesized surface-active fatty acid-protic ionic liquids (FA-PILs), based on tetramethylguanidinium cation and different natural hydrophobic fatty acid carboxylates, have been investigated with the aim of developing a pH-sensitive nanostructured drug delivery system for cutaneous administration in the skin cancer therapy. The capability of FA-PILs to arrange in micelles when combined with each other and with the non-ionic surfactant d-α-Tocopherol polyethylene glycol succinate (vitamin E TPGS) as well as their ability to solubilize imiquimod, an immuno-stimulant drug used for the treatment of skin cancerous lesions, have been demonstrated. The FA-PILs-TPGS mixed micelles showed pH-sensitivity, suggesting that the acidic environment of cancer cells can trigger nanostructures’ swelling and collapse with consequent rapid release of imiquimod and drug cytotoxic potential enhancement. The in vitro permeation/penetration study showed that the micellar formulation produced effective imiquimod concentrations into the skin exposed to acid environment, representing a potential efficacious and selective drug delivery system able to trigger the drug release in the tumor tissues, at lower and less irritating drug concentrations.

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“…On the other hand, in the past decade, room temperature ionic liquids (RTILs) have attracted considerable attention as possible replacements for organic solvents, because they are nonvolatile, nonflammable, thermally and chemically stable, highly polar, and environmentally friendly . These molten organic salts have been used together with CDs in a wide range of applications, such as in enantioseparation by electrophoresis, − in gas and high-performance liquid chromatographies, , and also in supramolecular chemistry, for the synthesis of new materials with many interesting properties, including polyrotaxanes and polypseudorotaxanes. − In all these fields, the knowledge of the characteristics of CD–RTIL interactions is of major interest.…”

Section: Introductionmentioning

confidence: 99%

Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins

Semino

Rodríguez

2015

J. Phys. Chem. B

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We have studied 1:1 inclusion complexes of two imidazole-based ionic liquids within β-cyclodextrin: 1-dodecyl-3-methylimidazolium and 1-butyl-3-methylimidazolium. By means of an adaptive biasing force scheme, we obtained the free energy profile along two different pathways, differing in the orientations of the head-to-tail vector with respect to the primary-secondary rim axis. Regarding 1-dodecyl-3-methylimidazolium, we found one minimum energy structure for each pathway, in which the hydrophobic tail remains embedded within the cyclodextrin, while the headgroup lies ∼11-12 Å from one of the rims; the structure where the polar head lies near the primary rim is the most stable. The analysis of the free energy of encapsulation of 1-butyl-3-methylimidazolium shows two minima for each insertion pathway, each of them associated with configurations where the imidazolium head lies close to one of the polar rims. As such, the most stable structure corresponds to one where the hydrophobic tail lies embedded within the cyclodextrin, while its head is localized near the secondary rim. The results are interpreted in terms of a simple model which captures the essential features that control the encapsulation process. A comparison with available experimental data is presented.

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Supramolecular Structures in the Presence of Ionic Liquids

Cited by 6 publications

References 345 publications

Self-recovering stimuli-responsive macrocycle-equipped supramolecular ionogels with unusual mechanical properties

Self-recovering stimuli-responsive macrocycle-equipped supramolecular ionogels with unusual mechanical properties

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins

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