Ultrasensitive sensor for L-penicillamine with chirality-induced amplification of benzo[3]uril electrochemiluminescence via supramolecular interactions

• Published in: Sensors and actuators. B, Chemical Chemical, 2022-07, Vol.362, p.131801, Article 131801
• Main Authors: Wu, Xiao-Fan, Ge, Qingmei, Jiang, Nan, Liu, Mao, Cong, Hang, Tao, Zhu
• Format: Article
• Language: English
• Subjects: Amplification; Aqueous environments; Benzouril; Chiral recognition; Chirality; Electrochemiluminescence; Electrochemiluminescence sensor; Enantiomers; Macrocyclic compounds; Penicillamine; Selectivity; Supramolecular compounds; Supramolecular interaction
• ISSN: 0925-4005; 1873-3077
• DOI: 10.1016/j.snb.2022.131801

Utilizing a novel concept of chiral amplification induced by host-guest interactions, a new macrocyclic compound, benzo[3]uril (BU[3]), was formed in a chiral microenvironment via the encapsulation of L-cysteine∙H+ (L-Cys∙H), and the electrochemiluminescence properties of BU[3] were sensibilized with the formation of a supramolecular complex. Based on this principle, an ultra-sensitive chiral electrochemiluminescence sensor was constructed to recognize the enantiomer of penicillamine (PA). This sensor exhibited high selectivity and sensitivity for L-PA compared to other reported values, with a detection limit of 10-12 mol·L-1 within a linear range of 10-5–10-10 mol·L-1, and no obvious electrochemiluminescence response to D-PA. The sensor presents high stability, good reproducibility, strong anti-interference ability, and acceptable recovery, which suggests an ability to quantitatively detect L-PA in an aqueous environment. •Chirality-induced amplification was realized by encapsulation of L-cysteine hydrochlorate within benzo[3]uril cavity.•The supramolecular complex was applied for the construction of an electrochemiluminescence sensor.•The ultrasensitive enantiorecognition for L-penicillamine was reached with extreme low LOD of 10-12 mol·L-1.