A facile ratiometric fluorescent chemodosimeter for hydrazine based on Ing-Manske hydrazinolysis and its applications in living cells

Mandapati V. Ramakrishnam Raju; Epperla Chandra Prakash; Huan Cheng Chang; Hong Cheu Lin

doi:10.1016/j.dyepig.2013.11.015

A facile ratiometric fluorescent chemodosimeter for hydrazine based on Ing-Manske hydrazinolysis and its applications in living cells

Mandapati V. Ramakrishnam Raju, Epperla Chandra Prakash, Huan Cheng Chang, Hong Cheu Lin

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	9-20
Number of pages	12
Journal	Dyes and Pigments
Volume	103
DOIs	https://doi.org/10.1016/j.dyepig.2013.11.015
State	Published - Apr 2014

Bibliographical note

Funding 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:
Copyright 2014 Elsevier B.V., All rights reserved.

Keywords

Charge transfer
Fluorescent probe
Ing-Manske hydrazinolysis
Semi-empirical calculations
Time resolved photoluminescence spectra
pH effects

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10.1016/j.dyepig.2013.11.015

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title = "A facile ratiometric fluorescent chemodosimeter for hydrazine based on Ing-Manske hydrazinolysis and its applications in living cells",

abstract = "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.",

keywords = "Charge transfer, Fluorescent probe, Ing-Manske hydrazinolysis, Semi-empirical calculations, Time resolved photoluminescence spectra, pH effects",

author = "{Ramakrishnam Raju}, {Mandapati V.} and {Chandra Prakash}, Epperla and Chang, {Huan Cheng} and Lin, {Hong Cheu}",

note = "Funding 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: Copyright 2014 Elsevier B.V., All rights reserved.",

year = "2014",

month = apr,

doi = "10.1016/j.dyepig.2013.11.015",

language = "English (US)",

volume = "103",

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AU - Ramakrishnam Raju, Mandapati V.

AU - Chandra Prakash, Epperla

AU - Chang, Huan Cheng

AU - Lin, Hong Cheu

N1 - Funding 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: Copyright 2014 Elsevier B.V., All rights reserved.

PY - 2014/4

Y1 - 2014/4

N2 - 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.

AB - 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.

KW - Charge transfer

KW - Fluorescent probe

KW - Ing-Manske hydrazinolysis

KW - Semi-empirical calculations

KW - Time resolved photoluminescence spectra

KW - pH effects

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ER -

A facile ratiometric fluorescent chemodosimeter for hydrazine based on Ing-Manske hydrazinolysis and its applications in living cells

Abstract

Bibliographical note

Keywords

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