Aggregation-Induced Enhanced Electrochemiluminescence from Organic Nanoparticles of Donor-Acceptor Based Coumarin Derivatives.

Organic nanoparticles (NPs) from donor-acceptor based coumarin derivatives, 6-[4-(N,N-diphenylamino)phenyl]-3-ethoxycarbonyl coumarin (DPA-CM), with an average size of 5.82 nm, were synthesized by a facile reprecipitation method using water as a poor solvent and tetrahydrofuran as a good solvent. Red-shifted absorption, blue-shifted photoluminescence emission, and aggregation-induced enhanced electrochemiluminescence (ECL) emission were observed for the DPA-CM NPs in aqueous solution compared with the original DPA-CM in organic solution. The aggregation-induced enhanced ECL emission is ascribed to the combined effects of the small size of the DPA-CM NPs, the restricted conformational relaxation in the NPs, and the good stability of the cationic radical of DPA-CM. A strong and stable ECL emission is obtained at the DPA-CM NPs modified glassy carbon electrode in the presence of tri-n-propylamine, and the ECL intensity of the DPA-CM NPs modified electrode is quenched linearly in the range of 0.05-50 μM with detection limit of 0.04, 0.2, and 0.4 μM for ascorbic acid, uric acid, and dopamine, respectively. This work shows an example of donor-acceptor based organic NPs as ECL emitters and their analytical applications to monitor biomolecules.