New pyrrolo[3,2-b]pyrroles with AIE characteristics for detection of dichloromethane and chloroform

Three new pyrrolo[3,2-b]pyrrole derivatives containing methoxyphenyl, pyrene or tetraphenylethylene (TPE) units (compounds 1-3) have been designed, synthesized and fully characterized. The aggregation-induced emission (AIE) properties of compounds 1-3 were tested in different water fraction (fw) of tetrahydrofuran (THF). The pyrrolo[3,2-b]pyrrole derivative 3 containing TPE units exhibited typical AIE features with an enhanced emission (similar to 32-fold) in the solid state versus in solution; compounds 1 and 2 exhibited an aggregation-caused quenching effect. In addition, the steric and electronic effects of the peripheral moieties on the emission behavior, both in solution and in the solid state, have been investigated. Moreover, pyrrolo[3,2-b]pyrrole 1 exhibits high sensitivity and selectivity for dichloromethane and chloroform solvents, with the system displaying a new emission peak and fast response time under ultraviolet irradiation. This article presents three new pyrrolo[3,2-b]pyrrole derivatives for understanding the relationship between the molecular structure on the emission behavior. In addition, the compound pyrrolo[3,2-b]pyrrole 1 shows high sensitivity, and fast response time for dichloromethane and chloroform solvents detection under ultraviolet irradiation.image