Electronic Substitution Effect on ESIPT-Driven pH and Amine Sensing: Exploring Mechanism

It is required to have a more straightforward and easier way to check the quality of food to ensure the safety of the public health. The decomposition of meat protein results in ammonia and biogenic amines (BAs). Consequently, to evaluate the safety and quality of meat products throughout the storage, transit, and consumption depends on the sensitive detection of the released BAs. Here, we have designed and synthesized three luminescent-based probe molecules, which originated from 2-(2-hydroxyphenyl) benzothiazole (HBT) derivatives and showed the excited state-induced proton transfer (ESIPT) phenomenon. The two substituents (OMe and NO₂) were used rationally at the para position of HBT, and the electronic properties were evaluated using Hammett substituent constants. The proton donating ability of the O−H to the acceptor is largely facilitated by the presence of a strong electron-withdrawing group, which in this case is NO₂. The proton transfer rate can be controlled, and in this case, to a slower rate with the influence of the electron donating group OMe. The controllability of proton transfer led us to use it in pH sensing. A prominent and multi-color change with pH variation was observed in the case of the OMe substituted compound. These probes were further employed for amine sensing, and the limit of detection (LOD) was determined to be 28.6 μM and 61.34 nM for ammonia and hydrazine, respectively. In addition, strip-based detection of spoilage of chicken meat was studied for real-world applications via both contact and non-contact modes.