Design of Two Pyrazole-Based Sensors with Similar Configuration and Different Fluorescent Response to Anions

Two simple fluorescent anion receptors based on 1-phenyl-3-methylpyrozole-5-one-4-one phenylhydrazone (L1) and 1-phenyl-3-methylpyrozole-5-one-4-one p-nitrophenylhydrazone (L2) were designed, synthesized and characterized with H-1 NMR, COSY spectrum, C-13 NMR, ESI-mass and elemental analyse. Interestingly, two receptors with similar configuration exhibited different anion binding behaviors in DMSO solution. The results of Job plots and ESI-mass spectrum indicate that L1 bind anions such as F-, AcO-, H2PO (4) (-) to form 2:1 host-guest complexation, while L2 bind anions to form 1:1 host-guest complexation in the solution.