The
selective recognition of dopamine (DA) over other
neurotransmitter
analogues is difficult due to the similar molecular structure and
chemical reactivity. In this study, substitution-regulated chemical
reactivity of the sensing substrate is utilized to explore a novel
DA detection probe with satisfying selectivity. As a case study, 3,5-dihydroxybenzoic
acid (DHBA, carboxy-substituted resorcinol)-based probes have been
explored for selective and ratiometric DA sensing. The carboxy substitution
benefits the stabilization of the carbanion intermediate and the azamonardine
product, which enhances the reaction kinetics and thermodynamics and
subsequently facilitates selective DA recognition over other analogues
and interferents. By exploring DHBA emission as the internal reference,
ratiometric fluorescence variation is realized, which contributes
to sensitive DA analysis. With the combination of logic gate and fluorometric
analysis, DA detection in both low and high concentrations can be
readily achieved. In addition, the DA analysis in biological samples
and the enzymatic transformation of DA analogues in cerebrospinal
fluid samples are achieved by the proposed DHBA probe.