Abstract：The spectral properties of molecular probes are closely related to their chemical structures. Therefore, the study of the relationship between molecule structure and its spectral properties cannot be ignore for rationally designing molecular probes with excellent performance. In this paper, the asymmetric chlorofluoroboron dipyrrole dye was used as the matrix, and the electron-absorbing group with quinoline salt as the matrix structure was introduced through the Knoevenagel reaction. Only different substituents at the same position were changed. Four hydrogen sulfide molecular probes (BOD-NO2, BOD-H, BOD-BOC and BOD-NH2) were designed and synthesized to investigate systematically the performance differences caused by the change of substituents. The results proved that the accompanying change of the different quinoline salt was the different electron withdrawing ability of probe, which leaded to the change of the reaction performance of the probe with H2S. These four probes showed specifical responsiveness to H2S. With the enhancement of the electron absorption ability of the substituents, the rate and extent of nucleophilic substitution reaction between the probes and H2S increased, meanwhile the absorption spectrum red-shifted and the photoacoustic imaging effect was better. Finally, the probe BOD-NO2 with excellent photoacoustic performance was successfully screened out through the investigation of the probe structure-activity relationship, which responded specifically to H2S with fast response and high selectivity. This study provides a novel idea for the design of photoacoustic probes targeting H2S.
DONG Xuemei,ZHU Ning,WANG Rongchen et al. Rational Design and Structure-Activity Relationship of Hydrogen Sulfide Photoacoustic Probe[J]. Chemical Reaction Engineering and Technology, 2023, 39(1): 53-61.
