2023
DOI: 10.1039/d3cc02258g
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Enantioselective resolution of two model amino acids using inherently chiral oligomer films with uncorrelated molecular structures

Abstract: Preferential crystallization induced by chiral surfaces is an interesting alternative to isolate enantiopure antipodes. Herein, we take advantage of the outstanding enantiorecognition capabilities of inherently chiral oligomers to induce an...

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Cited by 5 publications
(5 citation statements)
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“…These supramolecular additives were used for the enantioselective crystallization of different chiral acids, obtaining good stereoselectivity in yielding crystals with high enantiomeric purities in conglomerates. With a similar philosophy, inherently chiral oligomers of the 2,2′-bis(2,2′-bithiophene-5-yl)-3,3′-bithianaphthene (BT 2 T 4 ) have been used as chiral surfaces for the enantioselective crystallization of amino acids [ 45 ]. Such oligomers are an unconventional family of π-conjugated polymers that exhibit intrinsic chiral properties since the stereogenic and electroactive elements coincide within the polymeric backbone.…”
Section: Unconventional Methods For Enantioselective Separationmentioning
confidence: 99%
See 1 more Smart Citation
“…These supramolecular additives were used for the enantioselective crystallization of different chiral acids, obtaining good stereoselectivity in yielding crystals with high enantiomeric purities in conglomerates. With a similar philosophy, inherently chiral oligomers of the 2,2′-bis(2,2′-bithiophene-5-yl)-3,3′-bithianaphthene (BT 2 T 4 ) have been used as chiral surfaces for the enantioselective crystallization of amino acids [ 45 ]. Such oligomers are an unconventional family of π-conjugated polymers that exhibit intrinsic chiral properties since the stereogenic and electroactive elements coincide within the polymeric backbone.…”
Section: Unconventional Methods For Enantioselective Separationmentioning
confidence: 99%
“…Such a fascinating feature allows the induction of favorable or unfavorable diastereomeric interactions between the chiral selector and the enantiomers of a given electroactive analyte, reflected in relatively significant thermodynamic potential differences between the two antipodes [ 46 , 47 ]. In this work, Flood et al obtained highly enantiopure crystals of D- or L-ascorbic acid (ee > 90%) on the surface of oligo-( R )- or oligo-( S )-BT 2 T 4 , respectively, by taking advantage of these favorable or unfavorable diastereomeric interactions, fine-tuning the crystallization rate [ 45 ]. Finally, the chiral-induced spin selectivity (CISS) phenomenon was exploited to develop a complete additive-free crystallization approach.…”
Section: Unconventional Methods For Enantioselective Separationmentioning
confidence: 99%
“…An interesting concept to improve enantioselective resolution is exploiting favorable and unfavorable diastereomeric interactions between one of the antipodes of a chiral analyte and an inherently chiral oligomer. Such interactions lead to a differentiation in terms of either thermodynamic redox potentials or crystallization rates, when these chiral π-conjugated macromolecules are used as heterogeneous catalyst or as crystallization template. , …”
Section: Introductionmentioning
confidence: 99%
“…Such interactions lead to a differentiation in terms of either thermodynamic redox potentials or crystallization rates, when these chiral π-conjugated macromolecules are used as heterogeneous catalyst or as crystallization template. 25,26 Recently, the synergy between the electromechanical pumping of polypyrrole, driven by bipolar electrochemistry (BE), 27 and the enantioselective capabilities of inherently chiral oligomers have been proposed as an interesting alternative for loading, separating, and releasing chiral analytes. 27 This unconventional hybrid chiral electro-pump, which is wirelessly activated by simply applying an electric field, can tow and release the enantiomers of chiral probes from one extremity to the other, with different retention times.…”
Section: ■ Introductionmentioning
confidence: 99%
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