Synthesis and photophysical properties of water-soluble sulfonato-Salen-type Schiff bases and their applications of fluorescence sensors for Cu2+ in water and living cells.
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 Cu(2+), the sulfonato-Salen-type ligands can be used as highly selective and sensitive turn-off fluorescence sensors for the detection of Cu(2+) in water and fluorescence imaging in living cells.
Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610041, China.
Li
L
Zhou
Peiying
P
Cai
Yan
Y
Feng
Jinghui
J
Cheng
Haifeng
H
Xiang
Jin
J
Liu
Di
D
Wu
Xiangge
X
Zhou
D002413:Cations, Divalent / Q000032:analysis; D002460:Cell Line; D003300:Copper / Q000032:analysis*; D005029:Ethylenediamines / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D042541:Intracellular Space / Q000737:chemistry; D008856:Microscopy, Fluorescence / Q000379:methods; D008958:Models, Molecular; D011650:Pulmonary Alveoli / Q000166:cytology; D020545:Respiratory Mucosa / Q000166:cytology; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry*; D012680:Sensitivity and Specificity; D012995:Solubility; D013050:Spectrometry, Fluorescence / Q000379:methods; D013056:Spectrophotometry, Ultraviolet; D013451:Sulfonic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000032:analysis*
D002413:Cations, Divalent; D005029:Ethylenediamines; D005456:Fluorescent Dyes; D012545:Schiff Bases; D013451:Sulfonic Acids; D014867:Water; D003300:Copper; C011452:disalicylaldehyde ethylenediamine