the visible change from colorless to yellow demonstrating the
expediency of the probe as a "naked eye" indicator for F ion in
Supplementary Material
water (Figure 7B).The probe was inert to other analytes and no
change in color was observed for any of these analytes. The
fluorescence turn-on response upon sensing of F ion was also
Supplementary material (complete experimental procedures,
and spectral data for new compound and details of photophysical
characterization data for probe 3) associated with this article can
be found, in the online version, at
confirmed by the appearance of green fluorescence of the
reaction mixture when cuvette images were taken under handheld
UV-lamp (ex = 365 nm) (Figure 7C). These results confirmed
References and Notes
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that the probe 3 is highly selective towards F ion.
4
Application of probe 3 was demonstrated by live cell
fluorescence imaging technique using HeLa cells. When cells
were incubated with only probe 3 (10 M in 1:100 DMSO-
3
Hudson, Z. M.; Wang, S. Acc. Chem. Res. 2009, 42, 1584-1596.
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2
o
DMEM v/v, pH = 7.4) at 37 C for 1h, no significant
fluorescence was observed (Figure 8 B-C). On the other hand,
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2
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v/v, pH = 7.4) for 30 min and then incubated with the probe 3 (10
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3
. (a) Krishnamachari, K. A. Prog Food Nutr Sci. 1986, 10, 279-
strong fluorescence inside these cells (Figure 8 E-F). These
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through the living cell membranes and its ability of sensing
3
4
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Figure 8. Cell images of HeLa cell: differential interference contrast
(
(
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(
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2
4
. Conclusions
8
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In summary, we have presented the design, synthesis, and
properties of a colorimetric and fluorometric probe for detection
of F in aqueous media. The probe displayed a 120-fold
enhancement in fluorescence intensity and a fluorescence
quantum yield enhancement of 56-fold upon addition of F . The
10. Bao, Y.; Liu, B.; Wang, H.; Tian, J.; Bai, R. Chem. Commun.
2011, 47, 3957-3959.
1
1. (a) Dong, M.; Peng, Y.; Dong, Y.-M.; Tang, N.; Wang, Y.-W.
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Wang, J.; Voitchovsky, K.; Song, X. Chem. Commun. 2014, 50,
probe exhibits high sensitivity and selectivity toward fluoride
over other interfering anions. The detection limit of the probe
was found to be 24.5 µM (i.e. 0.46 ppm) which is comparable
with the reported LOD values so far. A change in color from
colorless to yellow and non-fluorescent to green fluorescence
3
20-322; (c) Roy, A.; Kand, D.; Saha, T.; Talukdar, P. Chem.
Commun. 2014, 50, 5510-5513; (d) Roy, A.; Datar, A.; Kand, D.;
Saha, T.; Talukdar, P. Org. Biomol. Chem. 2014, 12, 2143-2149;
prove the significance of the probe in “naked-eye” detection of F
(e) Roy, A.; Kand, D.; Saha, T.; Talukdar, P. RSC Adv. 2014, 4,
in water. The cell permeability and ability of the probe to detect
F in live cell was also confirmed by live cell imaging.
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12. Hu, R.; Feng, J.; Hu, D.; Wang, S.; Li, S.; Li, Y.; Yang, G.
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1
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Acknowledgments
We acknowledge IISER Pune and DST-SERB (Grant No.
SR/S1/OC-65/2012) for financial supports. A.R. and T.S. thank
University Grand Commission (UGC) for research fellowships.
2
014,
from
http://www.openmolecules.org/propertyexplorer/applet.html.