A coumarin based highly selective fluorescent chemosensor for sequential recognition of Cu2+ and PPi

作者:Meng, Xianjiao; Cao, Duanlin; Hu, Zhiyong; Han, Xinghua; Li, Zhichun; Liang, Dong; Ma, Wenbing*
来源:Tetrahedron Letters, 2018, 59(49): 4299-4304.
DOI:10.1016/j.tetlet.2018.10.048

摘要

In this study, we have successfully synthesized a new coumarin based fluorescent chemosensor 1, in which tren and quinolone are introduced as receptors for sequential recognition of Cu2+ and PPi. The structure of chemosensor 1 was characterized by H-1 NMR, C-13 NMR and ESI-HR-MS. Sensor 1 showed an obvious "on-off" fluorescence quenching response toward Cu2+, and the quenching efficiency reached a maximum of 99.6% with the addition of 20 equiv. of Cu2+. The 1-Cu2+ complex showed an "off-on" fluorescence enhancement response toward PPi over many competitive anions, especially HPO42- and H2PO4-. The detection limit of sensor 1 was 1.9 x 10(-8) M to Cu2+ and 5.96 x 10(-8) M to PPi. In addition, sensor 1 showed a 1:1 binding stoichiometry to Cu2+ and sensor 1-Cu2+ showed a 2: 1 binding stoichiometry to PPi in CH3CN/HEPES buffer medium (9:1 v/v, pH = 7.4). The stable pH range of sensor 1 to Cu2+ and 1-Cu2+ to PPi was from 4 to 8.