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

Abstract

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.

Highly Efficient Aggregation-Induced Electrochemiluminescence of Polyfluorene Derivative Nanoparticles Containing Tetraphenylethylene

“…In addition, PNs-2 could also react with K 2 S 2 O 8 to produce a stronger cathodic ECL signal, which deserved our attention. As shown in Figure 3D, the reduction peak of bare GCE at −0.95 V vs. Ag/AgCl was attributed to the reduction of K 2 S 2 O 8 to generate strong oxidant intermediate SO 4 -⋅ (Liu et al., 2017). On PNs-2 modified GCE, it was slightly moved to −1.2 V and the reduction current in CV curve became larger.…”

Recent Advances in Aggregation‐Induced Electrochemiluminescence

“…For example, AIECL potentially favors bioanalyses. In 0.1 m pH 7.4 PBS solution, the quenching signal of DPA‐CM NPs for AA, UA, and DA shows linearly in the range 0.05–50 μ m with detection limits of 0.04, 0.2, and 0.4 μ m respectively (Figure ) . Additionally, the individual quenching constant dependent on the concentration of AA, UA, and DA was calculated to be 2.6×10 6 , 4.8×10 5 , and 2.9×10 5 m −1 .…”

“…In 0.1 m pH 7.4 PBS solution, the quenching signal of DPA-CM NPs for AA, UA, and DA shows linearly in the range 0.05-50 mm with detection limits of 0.04, 0.2, and 0.4 mm respectively ( Figure 13). [46] Additionally,t he individual quenching constant dependent on the concentration of AA, UA, and DA was calculated to be 2.6 10 6 ,4 .8 10 5 ,a nd 2.9 10 5 m À1 .T he largestv alue for AA provided ah ighly sensitiveb iosensor and ap romising detecting method in complex samples.…”

“…The first organic molecule for AIECL was made from coumarin derivatives in aqueous solution (Figure 9a). [46] 6-[4-(N,N-Diphenylamino)phenyl]-3-ethoxycarbonyl coumarin (DPA-CM) NPs were formed by ar eprecipitation method. First, DPA-CM in degassed THF was poured into water under sonication.…”

Aggregation‐Induced Electrochemiluminescence by Metal‐Binding Protein Responsive Hydrogel Scaffolds

“…The first paradigm of AIECL was reported for a pyridine‐containing Pt (II) complex in 2017 . Sequentially, several systems, including cyclometalated‐Ir (III) complex, organic nanoparticles, and polymer dots, may cause AIECL on the basis of the large differences of materials in organic and aqueous solubility. To the best of our knowledge, no metallic NC‐based AIECL has been reported.…”