College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, 211800, Jiangsu, China.
J Fluoresc. 2022 May;32(3):983-992. doi: 10.1007/s10895-022-02908-3. Epub 2022 Mar 1.
Chirality plays a pivotal role in drugs, agrochemicals and food additives et al. The enantiomers of a chiral molecule often show huge difference in bioactivity, metabolism, and toxicity et al. thereby, the recognition of chiral molecules shows an increasingly important priority. In this paper, a novel method for chiral fluorescence recognition based on anthracene fluorescent dyes (AD) ⊂ water-soluble pillar[5] arene containing phosphonic acid group (PWP[5]) is developed. The AD as guest molecule can complex with PWP [5] to form 1:1 AD ⊂ PWP[5] assembly, and this assembly can be further used as a fluorescent probe to identify D/L-phenylalanine and D/L-phenylalaninol by fluorescent titration. The fluorescence intensity of the assembly was significantly reduced for D-phenylalanine and D-phenylalaninol, while L-phenylalanine or L-phenylalaninol was added to AD ⊂ PWP[5] assembly, the fluorescence intensity of the assembly almost unchanged. Hence, the chiral recognition based on assembly between the achiral fused ring fluorescent dye and achiral PWP[5] was developed.
手性在药物、农用化学品和食品添加剂等方面起着至关重要的作用。手性分子的对映异构体在生物活性、代谢和毒性等方面往往存在巨大差异，因此，手性分子的识别显得越来越重要。本文开发了一种基于蒽荧光染料（AD）⊂含膦酸基团的水溶性聚轮烷（PWP[5]）的手性荧光识别新方法。AD 作为客体分子可以与 PWP[5]形成 1:1 的 AD⊂PWP[5]组装体，该组装体可进一步用作荧光探针，通过荧光滴定法识别 D/L-苯丙氨酸和 D/L-苯丙醇胺。组装体的荧光强度对 D-苯丙氨酸和 D-苯丙醇胺显著降低，而当 L-苯丙氨酸或 L-苯丙醇胺加入 AD⊂PWP[5]组装体时，组装体的荧光强度几乎不变。因此，在手性识别中，基于非手性稠环荧光染料和非手性 PWP[5]之间的组装来进行。
