5
inserted in Figure 11), the mono-Bodipy unit could maintain
same fluorescence. This result supported that both the crown
ether chain and the bis-Bodipy structure played the crucial roles
for the ACQ effect of compound 3b after binding K+.
3. Kamkaew, A.; Lim, S. H.; Lee, H. B.; Kiew, L. V. L.; Chung, Y.;
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1172.
O
O
O
O
1, KI
F
F
N
N
K2CO3, MeCN
Cl
2
2
O
Cl
O
O
O
B
I
O
O
O
2b (excess)
7. Yuan, M. J.; Li, Y. L.; Li, J. B.; Li, C. H.; Liu, X. F.; Lv, J.; Xu, J.
L.; Liu, H. B.; Wang, S.; Zhu, D. B. Org. Lett. 2007, 12, 2313-
2316.
4
None
Li+
O
I
O
O
O
K+
O
Na+
K+
180
160
140
120
100
80
8. Shen, B. X.; Qian, Y. Sensors and Actuators B, 2017, 239, 226-234.
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2017, 175, 269-275.
O
O
Mg2+
Ca2+
Ag+
Hg2+
Ni2+
Co2+
Zn2+
Pb2+
Cr3+
Al3+
N
F
N
B
F
stable fluorescence
before and after complexation
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60
40
20
Ba2+
0
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Biophys. J., 1995, 68, 2469-2473.
400
450
500
550
600
650
700
wavelength / nm
Figure 11 the synthetic route for Bodipy derivative 4, and the
fluorescent spectra and complexation mode of 4 with K+. λex
480 nm
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26, 7697-7707.
=
17. Sui, B. L.; Yue, X. L.; Tichy, M. G.; Liu, T. H.; Belfield, K. D.
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In conclusion, three novel bis-Bodipy 3a-3c with crown
ether chain were designed and synthesized in yields of 70~78%.
The complexation absorption and fluorescent spectra of
compound 3b for fourteen metal ions showed high selective
complexation for K+ with obvious ACQ effect. The K+ binding
behavior of receptor 3b was investigated in depth by fluorescent
titration, complexation FT-IR spectra, complexation 1H NMR
spectra, complexation ESI-MS spectra. The association constant
of compound 3b with K+ was 4.3×105 M-1 and 1:1 complex mode
was formed. The complexation mechanism was proposed as a
pseudo crown ether ring for binding K+, resulting in the closed
distance for two Bodipy and strong ACQ effect finally. The
contrast experiment of similar mono-Bodipy derivative 4 also
supported this proposed mechanism. These results implied that
both the crown ether chain and the bis-Bodipy structure were the
decisive factors for the ACQ effect of binding K+. This paper
presented firstly the Bodipy sensor based on the metal ion
complexation of pseudo crown ether ring, which provides a new
strategy for design and synthesis of novel Bodipy sensor for
metal ions or other guests.
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436.
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Acknowledgment. Financial support from the National
Natural Science Foundation of China (No: 21406036), Fujian
Natural Science Foundation of China (No. 2017J01571), the
Program for Chemical Talent Program of Fujian Normal
University and Undergraduate Innovation Program (cxxl-
2017150) were greatly acknowledged.
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1002-1007.
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