Effect of Conjugation Mode on Intramolecular Charge Transfer in Fabricating Acid-Responsive Fluorophores

Solid-state acid-responsive materials are promising for the tunability of their intrinsic properties. However, the relationship between molecular structure and emission shift as a response to acid stimuli has not been systematically studied. Herein, we report the effect of protonation and subsequent intramolecular hydrogen bonding on the photophysical properties of compounds (MPP-s, MPP-d, and MPP-d-CN) with different conjugation modes between the electron-donating dimethoxyl phenyl and the electron-withdrawing benzothiazole ring. The results established that the stronger the intramolecular charge transfer feature of the compound, the smaller is the emission shift after acid stimuli. Our studies also indicated that the conjugation mode significantly affected the solid-state packing mode: MPP-s and MPP-d tended to form dimers, while MPP-d-CN exhibited the strongest aggregation-induced emission enhancement (AIEE). The exploration of structure-property relationship would provide experimental and theoretical guidance in designing acid-responsive molecular switches and developing high-performance AIEE-active luminogens.