Phenylalaninol (PAL) is a significant chemical intermediate
widely
utilized in drug development and chiral synthesis, for instance, as
a reactant for bicyclic lactams and oxazoloisoindolinones. Since the
absolute stereochemical configuration significantly impacts biological
action, it is crucial to evaluate the concentration and enantiomeric
content of PAL in a quick and convenient manner. Herein, an effective
PAL enantiomer recognition method was reported based on a chiral ionic
covalent organic framework (COF) fluorescent sensor, which was fabricated
via one-step postquaternization modification of an achiral COF by
(1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl-carbonochloridate
(L-MTE). The formed chiral L-TB-COF
can be applied as a chiral fluorescent sensor to recognize the stereochemical
configuration of PAL, which displayed a turn-on fluorescent response
for R-PAL over that of S-PAL with
an enantioselectivity factor of 16.96. Nonetheless, the single L-MTE molecule had no chiral recognition ability for PAL.
Moreover, the ee value of PAL can be identified by L-TB-COF. Furthermore, density functional theory (DFT) calculations
demonstrated that the chiral selectivity came from the stronger binding
affinity between L-TB-COF and R-PAL
in comparison to that with S-PAL. L-TB-COF is the first chiral ionic COF employed to identify chiral
isomers by fluorescence. The current work expands the range of applications
for ionic COFs and offers fresh suggestions for creating novel chiral
fluorescent sensors.