Schiff base fluorescence probes for Cu2+ based on imidazole and benzimidazole

作者：Wang, Xingjian; Xu, Ting; Duan, Hongdong^*

来源：Sensors and Actuators B: Chemical , 2015, 214: 138-143.

DOI：10.1016/j.snb.2015.03.022

• Fluorescent probe
• Imidazole
• Benzimidazole
• Schiff base
• Cu2+

Two novel Schiff base fluorescence probes for Cu2+ were designed and synthesized by reactions between p-fluorobenzaldehyde, p-phenylenediamine and heterocyclic compound (including imidazole and benzimidazole). The optimized geometries, frontier orbitals, molecular orbital contributions and excitation energies for the probes were predicted at B3LYP/6-31G* by theoretical calculation. And the probes were characterized by FTIR, H-1 NMR, UV-vis and fluorescence spectroscopy. Test results showed the probes had a high selectivity for Cu2+ compared to other metal ions measured (Ag+, Co2+, Mg2+, Ni2+, Pb2+, Zn2+, Cd2+ and Fe3+). From test results, a high selectivity for Cu2+ was discovered in this type of probes, especially, the probe based on benzimidazole exhibited more significant enhancement in fluorescence intensity compared with imidazole-based due to its relative large conjugate rigid plane structure. The detection mechanism of the synthesized probes with high selectivity for Cu2+ was also discussed.

• 出版日期2015-7-31