posted on 2022-05-11, 18:07authored byXiaoxuan Wang, Song Xiang, Chunxuan Qi, Mingyu Chen, Xiaolong Su, Jun-Cheng Yang, Jingjing Tian, Hai-Tao Feng, Ben Zhong Tang
Enantioselective
recognition and separation have attracted much
attention in pharmaceutical analysis, food chemistry, and life science.
Herein, we propose an efficient strategy to achieve such purposes
using optically active luminogens with aggregation-induced emission
(AIE) characteristics. These AIE luminogens (AIEgens) show strong
enantiomeric discrimination for 12 kinds of chiral acids and unprotected
amino acids. In particular, an exceptionally high enantioselectivity
for d/l-Boc-glutamic acid was observed, as demonstrated
by the large difference between the formed AIEgen/acid complexes.
Due to the AIE effect, enantioselective separation was achieved by
aggregation of the AIEgens with one enantiomer in the mixed acid solution.
Through analysis of the fluorescence standard curve, the aggregates
of AIEgen/chiral acid possessed 90% d-analyte, from which
the enantiomeric excess (ee) value was assessed to be 80% ee. Such
a result is in good agreement with that (91% d-analyte and
82% ee) by chiral HPLC analysis. Thus, this simple one-step aggregation
method can serve as a preliminary screening tool for high-throughput
analysis or separation of chiral chemicals.