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Issue 11, 2013
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Naphthalimide trifluoroacetyl acetonate: a hydrazine-selective chemodosimetric sensor

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Abstract

The trifluoroacetyl acetonate naphthalimide derivative 1 has been synthesized in good yield. In acetonitrile solution, compound 1 reacts selectively with hydrazine (NH2NH2) to give a five-membered ring. This leads to OFF–ON fluorescence with a maximum intensity at 501 nm as well as easily discernible color changes. Based on a readily discernible and reproducible 3.9% change in overall fluorescence intensity, the limit of detection for 1 is 3.2 ppb (0.1 μM), which is below the accepted limit for hydrazine set by the U.S. Environmental Protection Agency (EPA). Compound 1 is selective for hydrazine over other amines, including NH4OH, NH2OH, ethylenediamine, methylamine, n-butylamine, piperazine, dimethylamine, triethylamine, pyridine, and is not perturbed by environmentally abundant metal ions. When supported on glass-backed silica gel TLC plates, compound 1 acts as a fluorimetric and colorimetric probe for hydrazine vapor at a partial pressure of 9.0 mm Hg, with selectivity over other potentially interfering volatile analytes, including ammonia, methylamine, n-butylamine, formaldehyde, acetaldehyde, H2O2, HCl, and CO2 being observed. Probe 1 can also be used for the detection of hydrazine in HeLa cells and does so without appreciable interference from other biologically abundant amines and metal ions.

Graphical abstract: Naphthalimide trifluoroacetyl acetonate: a hydrazine-selective chemodosimetric sensor

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Supplementary files

Article information


Submitted
28 Jun 2013
Accepted
13 Aug 2013
First published
14 Aug 2013

Chem. Sci., 2013,4, 4121-4126
Article type
Edge Article

Naphthalimide trifluoroacetyl acetonate: a hydrazine-selective chemodosimetric sensor

M. H. Lee, B. Yoon, J. S. Kim and J. L. Sessler, Chem. Sci., 2013, 4, 4121
DOI: 10.1039/C3SC51813B

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