A facile and sensitive fluorescent probe for hydrazine was successfully constructed, displaying excellent colorimetric and ratiometric responses towards hydrazine via Ing-Manske hydrazinolysis conditions in semi-aqueous buffer solution. Semi-empirical calculations as well as spectroscopic results revealed the signalling mechanism of the current probe under hydrazinolysis conditions, in which hydrazine exclusively deprotected the phthalimide group by an intermediate of phthalhydrazide. Extensive screening of pH effects on the probe with the aid of proton nuclear magnetic resonance and mass spectrometry supported the distinctive and diverse ratiometric responses under hydrazinolysis and basic hydrolysis conditions. Time resolved photoluminescence measurements of the probe further confirmed its discernible ratiometric responses probed at respective wavelengths. A distinctive ratiometric response under basic hydrolysis conditions and a successful utilization of probe towards hydrazine detection in living cells are demonstrated.
Bibliographical noteFunding Information:
We thank the National Science Council of Taiwan (ROC) for financial supports of this project through NSC 101-2113-M-009-013-MY2 and NSC 99-2221-E-009-008-MY2 .
Copyright 2014 Elsevier B.V., All rights reserved.
- Charge transfer
- Fluorescent probe
- Ing-Manske hydrazinolysis
- Semi-empirical calculations
- Time resolved photoluminescence spectra
- pH effects