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Inversion of Supramolecular Chirality by In Situ Hydrolyzation of Achiral Diethylene Glycol Motifs
journal contribution
posted on 2022-02-03, 17:14 authored by Shuting Wang, Laiben Gao, Nan Su, Li Yang, Fengli Gao, Xiaoqiu Dou, Chuanliang FengChiral
inversion of supramolecular assemblies is of great research
interest due to its broad practical applications. However, chiral
structure transition induced by in situ regulation of building molecules
has remained a challenge. Herein, left-handed fibrous assemblies were
constructed by C2-symmetic l-phenylalanine coupled with diethylene glycol (LPFEG) molecules.
In situ hydrolyzing terminal diethylene glycol motifs in LPFEG successfully
inverted the chirality of the nanofibers from left- to right-handedness.
The transition of right-handed fibers into left-handed fibers could
also be achieved via hydrolyzing DPFEG molecules. Circular dichroism
(CD) spectroscopy, 1D and 2D nuclear magnetic resonance (NMR) spectroscopy,
and Fourier transform infrared (FT-IR) spectroscopy revealed that
the back-folded achiral diethylene glycol played a vital role in L/DPFEG
molecular arrangements and removing terminal diethylene glycol could
induce the opposite rotation of molecular assemblies. Thanks to this
merit, the enantioselective separation of racemic phenylalanine was
obtained and the enantiomeric excess (ee) values
could achieve around ±20% after separation. This study not only
provides a new strategy to regulate the chiral structure via dynamic
modulation of terminal substituents but also presents a promising
application in the field of enantioselective separation.
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fourier transform infraredenantiomeric excess (<broad practical applicationsdpfeg molecular arrangementslpfeg successfully invertedhanded fibrous assembliesmolecular assemblieshanded fiberssupramolecular assembliesvital roleterminal substituentssitu regulationsitu hydrolyzationracemic phenylalaninepromising applicationphenylalanine coupledopposite rotationnew strategyee diethylene glycolcircular dichroismc also presents>< sub