Conjugated Polyelectrolyte Containing a High Density of Pendant Phenylboronic Acid Groups for Dopamine Detection

A fluorescent sensing system based on a conjugated polyelectrolyte was constructed to detect dopamine (DA) in complex samples. The conjugated polymer PFPE–PBA with poly[fluorenyl-alt-p-phenyleneethynylene] (PFPE) as the backbone and carrying four pendant phenylboronic acid (PBA) groups in each repeat unit was synthesized. PFPE–PBA was found to have good solubility in polar solvents. After optimization, glycine-NaOH at pH 10 was selected as the buffer, and the solvent composition of the system was set to methanol/water (9/1 by volume). Titration experiments showed that DA could effectively quench the fluorescence of the polymer solution with a response time within 60 s and a limit of detection of 23 nM. Polyols, cations, and other possible interfering substances do not significantly affect the fluorescence of the polymer, thereby allowing for the highly selective detection of DA. Furthermore, quantitative determination of DA in spiked serum and artificial urine samples was successfully demonstrated, with recoveries ranging from 96.7 to 104%. Preliminary mechanism studies suggest that the pedant PBAs capture DA via reaction with the catechol group, and the fluorescence quenching is most likely due to the photoinduced electron transfer between the aromatic part of DA and the conjugated backbone. This study provides a general strategy for the future design of conjugated polyelectrolyte-based sensing systems.