Synthesis and photophysical properties of water-soluble sulfonato-Salen-type Schiff bases and their applications of fluorescence sensors for Cu in water and living cells |
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| Authors: | Li Zhou Peiying Cai Yan Feng Jinghui Cheng Haifeng Xiang Jin Liu Di Wu Xiangge Zhou |
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| Affiliation: | 1. Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610041, China;2. Laboratory of Stem Cell Biology, State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610064, China |
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| Abstract: | A series of water-soluble sulfonato-Salen-type ligands derived from different diamines including 1,2-ethylenediamine (Et-1–Et-4), 1,2-cyclohexanediamine (Cy-1 and Cy-2), 1,2-phenylenediamine (Ph-1–Ph-3 and PhMe-1–PhMe-4), and dicyano-1,2-ethenediamine (CN-1) has been designed and prepared. Sulfonate groups of ligands ensure good stability and solubility in water without affecting their excited state properties. These ligands exhibit strong UV/Vis-absorption and blue, green, or orange fluorescence. Time-dependent-density functional theory calculations have been undertaken to reveal the influence of ligand nature, especially sulfonate groups, on the frontier molecular orbitals. Since their fluorescence is selectively quenched by Cu2+, the sulfonato-Salen-type ligands can be used as highly selective and sensitive turn-off fluorescence sensors for the detection of Cu2+ in water and fluorescence imaging in living cells. |
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| Keywords: | Salen Schiff base Cu2+ fluorescence sensor Water soluble Sulfonate group TD-DFT calculation |
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