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A dansyl-appended N-heterocycle for Cu2+ and S2- recognition via a displacement mode
Xu Wang1, Peng Xia1, Xiaohuan Huang1
1Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, PR China.
Abstract:
A novel l-proline based heterocycle 3 of C2 symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu2+ ion, and their interaction induces a remarkable fluorescence quenching in DMSO:H2O=9:1 (HEPES buffer, 0.01M, pH7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu2+ complex exhibit specific fluorescence recovery upon addition of S2-, even in the presence of S2O32-, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of 1H NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential "on-off-on" fluorescence bio-imaging of the heterocycle 3 to Cu2+ and S2- was carried out in HeLa cells.
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