Methyl position affect the fluorescence performance of HBT derivatives for the detection of hypochlorite under...

Five fluorescent derivatives of hydroxyphenyl-benzothiazole (HBT) with different methyl positions at the hydroxyphenyl group were synthesized with good yield. Their reactivity and fluorescent response to hypochlorite were carefully studied. It was found that the HBT derivatives with meta-methyl (3-HBT or 5-HBT) showed the highest reactivity to hypochlorite under basic conditions, accompanied by the most efficient fluorescence quenching, whereas HBT derivatives with ortho or para methyl exhibited the least reactivity to hypochlorite. The LUMO and HOMO of 3-HBT were further verified to explain the fluorescence behavior by density functional theory (DFT) calculation. The excellent selectivity of 3-HBT toward hypochlorite against other reactive oxygen species (ROS) was also evaluated under the same conditions. The compounds emit bright green fluorescence in a solid-state, which is convenient for designing sensing devices for hypochlorite in water samples. Thus, the HBT derivatives with meta methyl (3-HBT) were successfully applied to fabricate paper sensors for the quantification of hypochlorite in tap water. Hence, the fluorescent 3-HBT exhibits great promise as a selective and sensitive hypochlorite probe in chemical and biological applications.