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 1 H NMR, COSY spectrum, 13 C NMR, ESI-mass and elemental analyse. Intere...

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Bibliographic Details
Published in:Journal of fluorescence 2010, Vol.20 (1), p.3-8
Main Authors: Li, Yaping, Shao, Jie, Yu, Xudong, Xu, Xiufang, Lin, Hai, Cai, Zunsheng, Lin, Huakuan
Format: Article
Language:English
Subjects:
Analytical Chemistry
Anions
Anions - analysis
Anions - chemistry
Binding
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Complexation
Drug Design
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Nuclear magnetic resonance
Original Paper
Phenylhydrazines - chemistry
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Receptors
Sensors
Spectrum Analysis
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Summary: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 1 H NMR, COSY spectrum, 13 C 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 − , H 2 PO 4 − to form 2:1 host-guest complexation, while L2 bind anions to form 1:1 host-guest complexation in the solution.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-009-0514-7