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New Journal of Chemistry
Page 6 of 8
DOI: 10.1039/C8NJ00589C
ARTICLE
Journal Name
corresponding 1,8-naphthalimide moieties with a 4- Foundation of the Key Laboratory of Synthetic, Natural
substituted amino. The proposed structure of the Functional Molecule Chemistry of the Ministry of
1
products was verified via H NMR, 13C NMR, and MS (Figs. Education (31270388), and from the National Natural
Science Foundation of China (81773603).
S9-S11) (scheme 1). Using this new strategy, we rapidly
obtained the 4-amino-1,8-naphthalimide, which was
generated from probe 2-AA. Moreover, probably because
of the solvent effect, this 4-amino-1,8-naphthalimide
emitted blue and yellow-green fluorescence in different
solvents when illuminated by a hand-held UV lamp (365
nm) (Fig. S12).
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To further investigate the biological applications of probe
2, fluorescence microscopy experiments were performed
on garlic slice tissue, which is abundant in AA (79 mg/100
g). First, dehydrated garlic was sliced using a freezing
microtome. Unbroken slices were used for fluorescence
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times with ethyl alcohol (Fig. 8B). The fluorescent
microscopy image of the slice showed a little weak blue
and green fluorescence at the excitation wavelengths of
405 and 488 nm (Figs. 8E and 8H), respectively, indicating
that probe 2 was capable of reacting with endogenous AA
with high sensitivity. In a further experiment, garlic slice
tissue was pretreated with probe 2, and then incubated
with AA (40 μM): significant fluorescence was observed
(Figs. 8F and 8I). These results indicate that probe 2 can
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Conclusion
In summary, we designed and synthesized three
chemosensors based on a 1,8-naphthalimide moiety with
an azide group at different sites for fluorescence turn-on
detection of AA via a novel and convenient redox strategy.
The results of the investigation showed that the 4-amino-
1,8-naphthalimide formed rapidly through the reaction
between probe 2 and AA. Although reduced by AA, probe
1
with the 4-substituted azide group showed no
fluorescence enhancement because of the PET process. In
contrast to probe 3 with a 3-substituted azide group,
probe 2 showed high selectivity toward AA, and was
easier to reduce. Moreover, probe 2 acted as a fluorescent
sensor to visualize AA in garlic slice tissues through the
blue and green emission channels.
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Acknowledgments
27. R. Liu, R. Yang, C. Qu, H. Mao, Y. Hu, J. Li and L. Qu, Sens.
Actuators B, 2017, 241, 644-651.
We are grateful for financial support from the Open
6 | J. Name., 2018, 00, 1-3
This journal is © The Royal Society of Chemistry 2018
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