The development of
enantioselective recognition is of great significance
in medical science and pharmaceutical industry, which associates with
the molecular recognition phenomenon widely observed in biological
systems. In particular, the facile and straight achievement of visual
enantioselective recognition has been drawing increasing consideration,
but it is still a challenge. Herein, a heterochiral diphenylalanine-based
gelator (LFDF) is synthesized, presenting left-handed nanofibers during
self-assembly in ethanol, which accomplishes the phenylalaninol enantiomer
recognition on multiple platforms. When adding l- or d-phenylalaninol into LFDF supramolecular solution followed
by ultrasonic treatment, precipitate and gel are formed, respectively.
Meanwhile, LFDF supramolecular gel completely collapses in a minute
after dropping l-phenylalaninol, while the gel almost remains
when d-type is employed. Moreover, a fluorescent supramolecular
xerogel (ThT–LFDF) is fabricated by combining the LFDF gelator
with thioflavine T (ThT), which could detect l-phenylalaninol
accompanying with fluorescence quenching while d-type with
barely decreasing. And the ThT–LFDF xerogel system shows a
good sensitivity (reaches to ppm) for the detection of l-phenylalaninol.
It is found that the chirality of the assembled nanofibers, as well
as amino and carboxyl of phenylalaninol, plays a critical role on
the discrimination process. The multiple and visible enantioselective
recognition of phenylalaninol through chiral supramolecular self-assemblies
shows potential applications in the fields of medical science and
pharmaceutical industry.