Chiral Fluorescent Recognition by Naphthalimide

• Published in: Journal of fluorescence 2020-05, Vol.30 (3), p.679-685
• Main Authors: Chen, Xuanming, Hu, Na, Wei, Huifeng, Wang, Haibo
• Format: Article
• Language: English
• Subjects: Analytical Chemistry; Assembly; Biochemistry; Biological and Medical Physics; Biomedical and Life Sciences; Biomedicine; Biophysics; Biotechnology; Bridged-Ring Compounds - chemistry; Chirality; Enantiomers; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent indicators; Imidazoles - chemistry; Molecular Conformation; Naphthalimides - chemistry; Original Article; Pharmacology; Phenylalanine; Phenylalanine - analogs & derivatives; Phenylalanine - analysis; Recognition; Stereoisomerism; Titration; Toxicity
• ISSN: 1053-0509; 1573-4994
• DOI: 10.1007/s10895-020-02539-6

Chirality plays a very important role in medicine, biochemistry and other fields. Because the enantiomers of chiral drugs often show different pharmacology activity, metabolism, and toxicity, therefore, the recognition of chiral molecules is very important, and has become a hot spot and frontier of modern chemical research. In this paper, a new method for recognizing chiral molecular based on naphthalimide dye(NA)⊂cucurbit[5]uril(CB[7]) assembly is developed. NA as guest can be combined with the host CB[7] to form a 1:1 NA⊂CB[7] assembly. Furthermore, this assembly was used as a fluorescent probe to recognize D/L-phenylalanine and D/L-phenylalaninol by fluorescence titration. When D-phenylalanine or D-phenylalaninol was added to NA⊂CB[7] assembly, the fluorescent intensity of assembly was partially quenched, but when L-phenylalanine or L-phenylalaninol was added to NA⊂CB[7], the fluorescence intensity of the assembly almost unchanged. Herein, chiral recognition platform based on achiral NA⊂achiral CB[7] was constructed.