C. Jin et al. / Tetrahedron Letters 54 (2013) 796–801
801
Figure 7. The color changes of receptors 2 (above) and 3 (below) (20 lM) when treated with 10 equiv of various anions in DMSO solutions.
ꢀ
L.; Liu, L.; Fang, R.; Deng, C.; Han, J.; Hu, H.; Lin, C.; Wang, L. Tetrahedron Lett.
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H2PO4 which are in agreement with the results of the UV–vis
spectra changes.
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In this Letter, we synthesized and discussed the sensing proper-
ties of three new calix[4]arene-based anion receptors 1–3 with bis-
squaramide moieties. The receptor 1 selectively binds biologically
important H2PO4ꢀ, Fꢀ, and AcOꢀ ions via stronger hydrogen bond
interaction than (thio)urea counterparts whereas 2 and 3 are
deprotonated by basic anions via acid–base interaction mode.
Receptors 2 and 3 exhibit prominent ‘naked-eye’ color changes
with basic anions such as Fꢀ and AcOꢀ through efficient deprotona-
tion. These results pave a way for the development of designing
and studying colorimetric receptors for anions with squaramide
moieties. We are currently working on developing novel receptors
based on calixarene platform using squaramide moieties to im-
prove the selectivity of anion recognition.
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We gratefully thank the financial support of National Natural
Science Foundation of China (No. 21102073, 21072093), the Doc-
toral Fund of Ministry of Education of China (20090091110017),
and the Natural Science Foundation of Jiangsu (BK2011055).
Supplementary data
Supplementary data (general experimental methods, synthetic
procedures, 1H NMR, 13C NMR, ESI-MS, UV–vis titration, NMR titra-
tion and crystal data) associated with this article can be found, in
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