Alzheimer's disease is a progressive neurodegenerative disorder with an insidious onset of symptoms. At present, there are no treatments that can effectively stop or reverse the disease from progressing. The development of effective methods for early diagnosis and treatment of Alzheimer's disease is therefore still urgently needed. In this article, we designed a family of Q-series probes (Q16∼Q21) that bind to Aβ aggregates by introducing different electron donors to bind to benzothiazole salts electron acceptors with different substituents to achieve imaging and photooxidation of aggregated Aβ proteins. The structure of the six probes was composed of N, N-dimethylaminophenyl and triphenylamine (donor groups), benzothiazole salts (acceptor groups), and π-conjugated double bonds. Among them, the probe Q17 with triphenylamine as the electron donor had a good singlet oxygen production efficiency, which can effectively carry out photooxidation after combining with Aβ aggregates, effectively reducing the degree of aggregation, and the cytotoxicity of Aβ aggregates was significantly reduced after bright light oxidation through cell experiments, which has great potentials in the treatment of Aβ photooxidation. On the other hand, probes Q16 and Q18 with N, N-dimethylaminophenyl as donors had excellent imaging abilities, good affinities for Aβ (Kd-Q16 = 26.95 nM, Kd-Q18 = 21.56 nM), can effectively image Aβ plaques in AD mouse brain slices and monitor the change of cell viscosity, and have a good application prospect in fluorescence imaging.