Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition
Jiaqiao Yang, Cheng Qian, Hanyu Su, Ji Zhang, Shanshan Yu, Xiao‐Qi Yu, Lin Pu
Abstract
High Resolution Image Download MS PowerPoint Slide Highly fluorinated naphthyl aldehyde 1 and binaphthyl aldehyde ( R )- 2 were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from 1 to ( R )- 2 in the fluorescent detection of cysteine has been discovered. This is attributed to the increased structural rigidity of the axially chiral binaphthyl unit in ( R )- 2 upon reaction with cysteine to form the corresponding thiazolidine product. The fluorous-phase-based detection of cysteine not only can allow the analysis to be conducted in a phase away from the interference of other organic and inorganic species but also results in significantly increased fluorescence response.