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Figure 5. The pH effect on DQ and its complex with Cd2+ and Zn2+
.
absorptions of O–H (3446 cmÀ1), C@N (1610 cmÀ1), and C–O
(1100 cmÀ1) of imidic acid tautomer. For DQ and DQ-Cd2+ complex,
the typical stretching absorptions of N–H (3270 cmÀ1, 3190 cmÀ1
)
, ) of amide tautomer were
and C@O (1690 cmÀ1 1670 cmÀ1
observed.
Furthermore, pH effect on fluorescence of DQ was investigated
in water. As shown in Figure 5, in the pH range of 6–9, DQ and its
complex with Zn2+ and Cd2+ show very stable fluorescence, indicat-
ing that the probe could be used under common environmental
and physiological condition.
In conclusion,
a water-soluble quinoline-based fluorescent
probe (DQ) for Cd2+ and Zn2+ was designed and synthesized. The
new probe coordinates with Zn2+ and Cd2+ in different binding
models and gives quite different fluorescent signals for these two
ions. Moreover, the probe shows nanomole affinity and high selec-
tivity to Zn2+ and Cd2+. All these make DQ an excellent candidate
fluorescent probe that can distinguish Zn2+ from Cd2+ for biological
and environmental applications.
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Acknowledgments
We acknowledge financial support by NSFC (21102002,
21272223), Natural Science Foundation of Education Department
of Anhui Provience (KJ2010A028), and 211 Project of Anhui Univer-
sity for supporting the research.
11. Data for DQ: 1H NMR (400 MHz, DMSO-d6, ppm): d 2.63 (3H, s), 3.52 (2H, s),
3.97 (4H, s), 7.28–7.31 (2H, m), 7.37–7.39 (1H, d, J = 8.46 Hz), 7.47–7.79 (2H, d,
J = 7.73 Hz), 7.76–7.79 (2H, t, J = 7.63 Hz), 7.87–7.93 (2H, m), 8.19–8.21 (1H, d,
J = 8.44 Hz), 8.36 (1H, s), 8.61–8.63 (2H, d, J = 4.52 Hz), 10.84 (1H, s). 13C NMR
(100 MHz, DMSO-d6, ppm): d 24.81, 58.85, 60.40, 115.62, 122.36, 122.63,
123.32, 123.62, 127.02, 128.53, 136.12, 136.57, 136.72, 144.30, 149.42, 157.35,
157.97, 170.21. Anal. Calcd for C24H23ON5: C, 72.52; H, 5.83; N, 17.62. Found: C,
71.49; H, 5.88; N, 17.65. The detail experiment and the data of other
intermediates are in the Supplementary data.
12. Hirano, T.; Kikuchi, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 6555.
13. (a) McDonough, M. J.; Reymolds, A. J.; Lee, W. Y. G.; Jolliffe, K. A. Chem.
Commun. 2006, 2971; (b) Lu, C. L.; Xu, Z. C.; Cui, J. N.; Zhang, R.; Qian, X. H. J.
Org. Chem. 2007, 72, 3554.
Supplementary data
Supplementary data (synthetic and experimental details) asso-
ciated with this article can be found, in the online version, at
References and notes
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