Development of novel aromatic ambidextrous gelators based on molecular design

Tsuge, Akihiko; Matsumoto, Shinnosuke; Hashimura, Daiki; Araki, Koji

doi:10.1016/j.tetlet.2019.151501

Cited by 8 publications

(1 citation statement)

References 29 publications

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“…In terms of achievement to develop excellent ambidextrous gelators based on molecular design we have already reported preparation and ambidextrous properties of the glutamate‐based aromatic compounds consisting of alkyl chains as a hydrophobic part and ethylene glycol units as a hydrophilic part [8] . In principle an ambidextrous gelator has to be an amphiphile because they need to dissolve in water and organic solvents, indicating that combination of a hydrophobic part and a hydrophilic part is crucial as well as some components responsible for weak intermolecular noncovalent interactions such as effective H‐bonding, π‐π stacking, charge‐transfer interaction and van der Waals interactions.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Ambidextrous Gelators Having Ethanolamine Moiety

2021

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Although tremendous research investigations on organogelators and hydrogelators have been conducted, the reports about the ambidextrous gelators capable of gelating both organic solvents, especially, apolar solvents and water are very limited. In order to create efficient ambidextrous gelators it should be necessary to take a bottom‐up approach. Thus, according to molecular design the amphiphilic compounds consisting of glutamate‐based structure having two long alkyl chains and the ethanolamine moiety have been prepared. The compounds having C6 and C7 alkyl chains have been found out to work as an excellent ambidextrous capability because they can only gelate water and apolar solvents. Although the compounds having C9 and C10 alkyl chain showed no gelation in water, by introduction of an ammonium cation into these compounds ambidextrous properties were gained. Ambidextrous ability can be imparted to the compound having no ambidextrous properties by mixing with a small amount of an authentic ambidextrous gelator.

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Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Ambidextrous Gelators Having Ethanolamine Moiety

2021

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Enantioseparation via Chiral Supramolecular Gels Comprising Ambidextrous Gelators Based on β‐Peptide‐type Primary Amines

Kodama,

Obata,

Hirose

2024

ChemPlusChem

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While β‐peptides have been paid attention due to their diverse secondary structures, their application to the design of low‐molecular‐weight gelators (LMWGs) is less explored. In this work, chiral cyclic β‐amino acid‐based β‐peptides were developed as ambidextrous LMWGs, wherein multiple hydrogen bonds between the amide moieties led to high gelation ability. Their molecular assembly was elucidated using spectroscopies, microscopy, and X‐ray analysis. Further, the supramolecular gel was used as a platform for the enantioselective extraction of (S)‐naproxen from its racemate under optimized conditions. These findings have expanded the utility of β‐peptides and shown the potential of supramolecular gels as a distinct dynamic medium for enantiomer separation.

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