D-π-A-π-D-Configured Imidazole-Tethered Benzothiadiazole-Based Sensor for the Ratiometric Discrimination of Picric Acid: Applications in Latent Fingerprint Imaging.

A tetraphenyl imidazole-appended benzothiadiazole-based fluorogenic probe (4,7-bis(4-(1,4,5-triphenyl-1 H -imidazol-2-yl)phenyl)benzo[ c ][1,2,5]thiadiazole ( BIPT )) has been successfully synthesized and characterized by NMR and high-resolution mass spectrometry (HRMS) spectral analyses. A low limit of detection (LOD) can be achieved to detect picric acid (PA; 7.89 nM). When benzothiadiazole acceptors are incorporated in the D-A-D probe, it can produce a large Stokes shift (206 nm) as a result. Fascinatingly, the fluorescence signals of BIPT were ratiometrically induced by the interaction with PA and exhibited an apparent emission shift from pink to green. The detection process of BIPT is triggered by an intermolecular charge transfer process, as the charge transfer takes place from the electron-rich imidazole to the electron-deficient PA. Moreover, fluorescence detection of PA has been employed in paper strips. Advantageously, sensor BIPT can potentially be applied to contact mode and real-time detection of PA in environmental water samples. Additionally, the BIPT sensor has been successfully employed for latent fingerprint imaging. The study provides clear insights into the rational design of chemosensors for sensing and real-time applications.