Wang Ling, Wei Yu-Ping, Liu Xing-Pei, Chen Jingshuai, Mao Chang-Jie, Jin Baokang
Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Ministry of Education), School of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601, China.
Langmuir. 2024 Sep 9. doi: 10.1021/acs.langmuir.4c02213.
Aggregation-induced electrochemiluminescence (AIECL) combines the merits of aggregation-induced emission (AIE) and electrochemiluminescence (ECL), which has become a research hot spot in recent years. Therefore, we synthesized a novel AIE compound ()-3-(4-(2-butyl-1,3-dioxo-2,3-dihydro-1-benzo[de]isoquinolin-6-yl)phenyl)-2-(4-(1,2,2-triphenylvinyl)phenyl)acrylonitrile (TPENI) with a donor-acceptor (D-A) structure, that is, a simple peripheral modification of 4-(2-butyl-1,3-dioxo-2,3-dihydro-1-benzo[de]isoquinolin-6-yl) benzaldehyde (NI-CHO) with AIE-active tetraphenylethylene (TPE) to achieve the transition of NI-CHO from aggregation-caused quenching (ACQ) to an AIE molecule. When TPENI was in the aggregated state, the luminescence intensity was significantly enhanced due to the TPE structural unit restricting the free rotation of the intramolecular benzene ring, as well as the π-π stacking interactions of the molecules, which was conducive to the preparation of TPENI NPs as ECL materials. Satisfactorily, we found that the ECL intensity of TPENI NPs was increased by about 4.8-fold compared with that of the molecules dispersed in organic solution, and the stability reached about 1000 s. Based on the excellent ECL properties of TPENI NPs, an "on-off-on" ECL biosensor with a wider detection range (1 fg/mL to 100 ng/mL) and a lower detection limit of 0.20 fg/mL (S/N = 3) was proposed for sensitive analysis of a carcinoembryonic antigen (CEA). Overall, this work provided a new approach to the realization of AIECL and laid the foundation for the application of naphthalimide derivatives in ECL.
聚集诱导电化学发光(AIECL)结合了聚集诱导发光(AIE)和电化学发光(ECL)的优点,近年来已成为研究热点。因此,我们合成了一种具有供体-受体(D-A)结构的新型AIE化合物()-3-(4-(2-丁基-1,3-二氧代-2,3-二氢-1-苯并[de]异喹啉-6-基)苯基)-2-(4-(1,2,2-三苯乙烯基)苯基)丙烯腈(TPENI),即通过具有AIE活性的四苯乙烯(TPE)对4-(2-丁基-1,3-二氧代-2,3-二氢-1-苯并[de]异喹啉-6-基)苯甲醛(NI-CHO)进行简单的外围修饰,实现NI-CHO从聚集导致猝灭(ACQ)到AIE分子的转变。当TPENI处于聚集状态时,由于TPE结构单元限制了分子内苯环的自由旋转以及分子间的π-π堆积相互作用,发光强度显著增强,这有利于将TPENI纳米粒子制备为ECL材料。令人满意的是,我们发现与分散在有机溶液中的分子相比,TPENI纳米粒子的ECL强度提高了约4.8倍,稳定性达到约1000秒。基于TPENI纳米粒子优异的ECL性能,提出了一种检测范围更广(1 fg/mL至100 ng/mL)、检测限更低(0.20 fg/mL,S/N = 3)的“开-关-开”ECL生物传感器,用于癌胚抗原(CEA)的灵敏分析。总体而言,这项工作为实现AIECL提供了一种新方法,并为萘酰亚胺衍生物在ECL中的应用奠定了基础。