A carbazole-based turn-on fluorescent probe for the detection of hydrazine in aqueous solution

Article abstract of DOI:10.1016/j.ica.2018.03.033

A carbazole-based fluorescent probe, 2-(9-ethyl-9H-carbazol-3-yl) isoindoline-1,3-dione, with a low detection limit (2.673 × 10^?6 M) for the detection of hydrazine is designed and synthesized based on Gabriel reaction. The probe responds selectively to hydrazine over other amino compounds with marked fluorescence enhancement. Moreover, test paper experiments indicated its great potential in the environment monitoring of hydrazine in aqueous solution.

Full text of DOI:10.1016/j.ica.2018.03.033

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Accepted Manuscript
Research paper
A carbazole-based turn-on fluorescent probe for the detection of hydrazine in
aqueous solution
Wei-Dong Wang, Yang Hu, Qiao Li, Sheng-Li Hu
PII:
S0020-1693(18)30148-8
https://doi.org/10.1016/j.ica.2018.03.033
ICA 18178
DOI:
Reference:
Inorganica Chimica Acta
To appear in:
Received Date:
Revised Date:
Accepted Date:
27 January 2018
20 March 2018
21 March 2018
Please cite this article as: W-D. Wang, Y. Hu, Q. Li, S-L. Hu, A carbazole-based turn-on fluorescent probe for the
detection of hydrazine in aqueous solution, Inorganica Chimica Acta (2018), doi: https://doi.org/10.1016/j.ica.
2018.03.033
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A carbazole-based turn-on fluorescent probe for the detection
of hydrazine in aqueous solution
Wei-Dong Wang, Yang Hu, Qiao Li, Sheng-Li Hu*
Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, Hubei
Collaborative Innovation Center for Rare Metal Chemistry, College of Chemistry and
Chemical Engineering, Hubei Normal University, Huangshi 435002, P. R. China
Abstract
A carbazole-based fluorescent probe, 2-(9-ethyl-9H-carbazol-3-yl) isoindoline-
1,3-dione, with a low detection limit (2.673× 10-6 M) for the detection of hydrazine is
designed and synthesized based on Gabriel reaction. The probe responds selectively to
hydrazine over other amino compounds with marked fluorescence enhancement.
Moreover, test paper experiments indicated its great potential in the environment
monitoring of hydrazine in aqueous solution.
Key words
Carbazole, Fluorometric, Hydrazine, Gabriel reaction.
1. Introdution
As a type of highly reactive base and reduction agent [1], hydrazine has also played
a vital role in pharmaceuticals, pesticides, dyes and emulsifiers [2-4]. However,
hydrazine is highly poisonous and the exposure of hydrazine in elevated levels could
*Corresponding author: E-mail：hushengli168@126.com Tel.: +86 0714 6515602 Fax: +86 0714
6515602
1

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cause serious damage to the liver, lungs, kidneys, especially for the human nervous
system [5-7]. As a result, it is necessary to develop the highly selective and sensitive
analytical methods for the detection of trace hydrazine in both environmental and
biological science.
Recently, the development of fluorescent probes toward metal ions, anions and
biomolecules has attracted great attention because of its simplicity, low cost, good
selectivity, and high sensitivity [8-12]. Of particular interest is the design of
“turn-on” fluorescent probes for selective detection because fluorescence
enhancement are more sensitive and more easily monitored than fluorescence
quenching [13-15]. A variety of fluorescent probes based on coumarin[16, 17] ,
naphthalimide [18-20 ], pyrazoline[21,22], benzothiazole [23], BODIPY[24],
fluorescein[25, 26] , pyrene and anthracene [27] for hydrazine have been reported.
[28, 29].
fluorescent probe for
d [30-36].
detection of
biomolecules
However, carbazole-based fluorescent chemosensors for hydrazine is still rare [37].
hydrazine
hydrazine
2

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hydrazine in
2. Experimental
2.1. Chemicals and apparatus
9-ethyl-9H- carbazol-3-amine (4) was synthesized according to the reported
method [38]. NMR spectra were measured on a Varian Mercury 300 spectrometer
operating. ESI-MS spectra were obtained on a Finnigan Trace MS spectrometer.
Absorption spectra were determined on UV-2501 PC spectrophotometer.
Fluorescence spectra measurements were performed on a Fluoro-Max-P
spectrofluorimeter. The X-ray crystal structure determinations of 1 were obtained on a
Bruker SMART APEX CCD system.
2.2. Synthesis of probe 1
The synthetic route of compound 1 is shown in Scheme 1.
To a 25 mL flask, 9-ethyl-9H-carbazol-3-amine (4) (1.0 mmol, 0.21 g) and
o-phthalic anhydride (1.0 mmol, 0.15 g) were added to acetic acid (7ml) and refluxed
for 6 h. Then acetic acid was removed and the afforded solid was purified by column
chromatography on silica gel to obtain 1 as a white solid (0.24 g, 71%). M.p.:
1
212-213°C (lit.[39], 212-213°C). H NMR(CDCl3, 300 MHz): δ1.43-1.48 (t, 3H),
4.36-4.44 (q, 2H), 7.72-8.11 (m, 11H); 13C NMR (CDCl3, 75MHz): 13.8, 37.6, 108.6,
10 8.8, 119.1, 119.3, 120.7, 122.61, 122.65, 123.2, 123.6, 124.5, 125.6, 126.1, 131.9,
134.2, 135.9, 139.3, 140.4, 168.1. ESI-MS: m/z 702.83 [2M+Na]+. Crystal data for
C22H16N2O2: Crystal size: 0.32×0.17×0.12 mm, monoclinic, space group P21/c. a =
3