A series of AIE dyes derived from shikimic acid: The thermo/pressure dependent fluorescence and application in the sensing of arginine

Transformation of renewable bio-feedstock to fine chemicals and functional materials are much desirable in chemistry and chemical engineering. Herein, a series of AIE dyes (compounds a-o) with thermo/pressure dependent fluorescence were revealed. Fifteen compounds (a-o) with the ortho-carboxyl diarylamine key structure were obtained from the renewable biomass molecule shikimic acid and ten of them exhibited typical AIE behavior. By changing the substituent groups that might affect the AIE property, the fluorescent emission of the AIE dyes could be changed from white to green or blue. Thermo/pressure dependent fluorescence emission was observed for the tested AIE molecules and the fluorescent intensity changes could be used as a quantified signal for the surrounding temperature. Moreover, substituent moderating effect for the AIE property of compounds a-o was revealed by using DFT calculation. In addition, organic nanoparticle fluorescent probe (ONFP) was prepared based on compound o and used in the selective and sensitive detection of arginine in real water.