AIEE-active dichlorobenzene and chlorobenzene ratiometric fluorescent probe based on [2.2]paracyclophane

Two AIEE-active [2.2]paracyclophanyl-based diester and monoester (1a and 1b) were facilely synthesized by one-pot method and applied as ratiometric fluorescent probe to detect dichlorobenzene (DCB) and chlorobenzene (CB). Compared with compound 1b, 1a exhibits high sensitivity and low detection limits for DCB and CB in dichloromethane (DCM), particularly, the detection sensitivities for ortho-dichlorobenzene (o-DCB), meta-dichlorobenzene (m-DCB) and chlorobenzene can be modulated by AIEE behavior with lower detection limits of 23.64, 56.27, and 5.92 ppm, respectively in THF/H₂O mixed solutions with water fraction (f_w) of 70 % due to the formation of aggregation-state. The X-ray structure analysis, theoretical calculations and photophysical properties in different solvents were investigated to reveal the distinctive photophysical behaviors of 1a and 1b. The facile synthesis, X-ray structure, AIEE modulated sensing properties for o-DCB, m-DCB, and CB in DCM and THF/H₂O mixed solutions make 1a potential application as fluorescent probe for trace DCB and CB detection in drinking water.