Synthesis of organogelling, fluoride ion-responsive, cholesteryl-based benzoxazole containing intra- and intermolecular hydrogen-bonding sites

Kim, Tae Hyeon; Kwon, Na Young; Lee, Taek Seung

doi:10.1016/j.tetlet.2010.08.053

Cited by 26 publications

(16 citation statements)

References 42 publications

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“…Two cyanostilbene amide derivatives 1 and 2 were easily synthesized by the reaction of the respective amine with the cholesteryl derivative in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) (Scheme S1, ESI †). 8 The chemical structures of two compounds were characterized using 1 H NMR, 13 C NMR, MS data, FT-IR, and elemental analysis.…”

Section: Gelation Propertymentioning

confidence: 99%

An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative

Zhang

Deng

et al. 2015

Soft Matter

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Two novel low molecular weight organogelators (LMOGs) 1 and 2 composed of a cholesteryl group, an amide group and various terminal cyanostilbene moieties were synthesized. They could form stable gels in p-xylene. In particular, 2 with more extended π-conjugation length showed remarkable gelation ability in many aromatic solvents, chloroform and chloroform-containing mixed solvents at a relatively low concentration. FT-IR and XRD spectra indicated that the difference between 1 and 2 in the gelation properties may result from the deviation of the intermolecular hydrogen bonding and π–π stacking as driving forces for the formation of the gels. Significantly, 2 can function as an efficient room-temperature phase-selective gelator (PSG) for potential application in the separation and recovery of various aromatic solvents from its mixture with water. Meanwhile, the gelator can be easily recovered and reused several times. Furthermore, the phase-selective gelation properties of 2 can provide a simple and feasible approach for the removal of the rhodamine B (RhB) dye from water.

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Section: Gelation Propertymentioning

confidence: 99%

An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative

Zhang

Deng

et al. 2015

Soft Matter

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“…Lee and co-workers, for example, have reported a fluorideresponsive gel system. 106 They synthesized an organogelator 62 (Fig. 32) containing a cholesterol unit with a fluorophore, 2-(2hydroxyphenyl)benzoxazole, linked via an amide group.…”

Section: Chemical Stimulimentioning

confidence: 99%

Recent advances in steroidal supramolecular gels

et al. 2012

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During the last decade or two the interest towards small molecules capable of self-assembly leading to gelation has increased intensively. The investigation of these supramolecular gels aims not only at understanding the fundamental processes underlying gel formation but also at development of new materials with a myriad of applications. Steroids are widely-spread natural products with a large and rigid steroidal nucleus combined with derivatizable functional groups leading to an adjustable polarity profile, which makes them attractive building blocks when designing novel low molecular weight gelators. Due to their unique properties, steroid-based supramolecular gels may find use in applications ranging from materials science and nanoelectronics to their application as reaction media or as sensing and responsive materials. Moreover, biomaterials based on steroidal gels may find use in biomedicine, drug delivery, regenerative medicine, and tissue engineering. This article summarizes the most recent advances in the field of steroidal supramolecular gels in terms of steroid-derived hydroand organogels, metallogels, two-component gels, and stimuli-responsive gels. Furthermore, the potential applications of the systems are discussed.

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“…It is fact that sensing of these anions demands precise design of receptors due to their strong basic nature and hydrogen bonding capabilities . Although a large number of fluorometric and colorimetric receptors for fluoride and phosphate‐based anions in solution phase is reported in the literature, supramolecular gelators capable of detecting fluoride are relatively less in number . Importantly, few examples are found where the self aggregation process of low molecular weight gelators is influenced in the presence of phosphate‐based anionic substrates …”

Section: Introductionmentioning

confidence: 99%

Cholesterol–based Bisamides on Biphenyl Backbone: A Case of Selective Visual Sensing of F⁻ and H₂PO₄⁻ through Breaking and Making of Gels

Ghosh

Panja

2016

ChemistrySelect

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Cholesterol linked bisamides 1–3 on biphenyl spacers have been designed and synthesized. Compound 1 forms gel in CHCl3 – n‐hexane (1:6, v/v) solvent and the gel is selectively collapsed into sol in presence of F− with a color change from yellowish white to greenish yellow. Presence of pyridinium amides in 2 and 3 showed different gelation behaviours. While the chloride salt 2 displayed gelation in CHCl3 in presence of H2PO4−, compound 3 formed gel in DMSO: H2O (1:2, v/v) without having any assistance of externally added anion. The gel derived from 3 underwent rapid gel to sol transition in presence of H2PO4− and F− anions and validated their visual sensing.

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Synthesis of organogelling, fluoride ion-responsive, cholesteryl-based benzoxazole containing intra- and intermolecular hydrogen-bonding sites

Cited by 26 publications

References 42 publications

An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative

An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative

Recent advances in steroidal supramolecular gels

Cholesterol–based Bisamides on Biphenyl Backbone: A Case of Selective Visual Sensing of F⁻ and H₂PO₄⁻ through Breaking and Making of Gels

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Synthesis of organogelling, fluoride ion-responsive, cholesteryl-based benzoxazole containing intra- and intermolecular hydrogen-bonding sites

Cited by 26 publications

References 42 publications

An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative

An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative

Recent advances in steroidal supramolecular gels

Cholesterol–based Bisamides on Biphenyl Backbone: A Case of Selective Visual Sensing of F− and H2PO4− through Breaking and Making of Gels

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Product

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Cholesterol–based Bisamides on Biphenyl Backbone: A Case of Selective Visual Sensing of F⁻ and H₂PO₄⁻ through Breaking and Making of Gels