W. Wei et al. / Tetrahedron Letters 52 (2011) 1422–1425
1425
2246; (h) Zhang, M.; Li, M. Y.; Zhao, Q.; Li, F. Y.; Zhang, D. Q.; Zhang, J. P.; Yi, T.;
Huang, C. H. Tetrahedron Lett. 2007, 48, 2329; (i) Zeng, Y.; Zhang, G. X.; Zhang,
D. Q.; Zhu, D. B. Tetrahedron Lett. 2008, 49, 7391; (j) Huang, S. T.; Ting, K. N.;
Wang, K. L. Anal. Chim. Acta 2008, 620, 120; (k) Bouffard, J.; Kim, Y.; Swager, T.
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Supplementary data
Supplementary data (synthesis and characterization data of
compounds 1 and 2, the procedure of electrochemistry experi-
ments, absorption titration of receptor 1 with Cys, absorption spec-
tral changes of receptor 2 with various amino acids and GSH,
absorption spectral changes of receptor 1 with MPA, Benesi–Hilde-
brand plots of receptor 1 with Cys and Hcy) associated with this
article can be found, in the online version, at doi:10.1016/
10. Chen, X. Q.; Zhou, Y.; Peng, X. J.; Yoon, J. Y. Chem. Soc. Rev. 2010, 39, 2120.
11. (a) Guy, J.; Caron, K.; Dufresne, S.; Michnick, S. W.; Skene, W. G.; Keillor, J. W. J.
Am. Chem. Soc. 2007, 129, 11969; (b) Matsumoto, T.; Urano, Y.; Shoda, T.;
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References and notes
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21. The anion binding and sensing properties of receptor 1 were also evaluated.
The preliminary experiments indicated that, in MeCN solution, the remarkable
spectral changes of receptor 1 were observed in the presence of 200 equiv of Fꢁ
AcOꢁ, H2PO4ꢁ, HSO4 and Clꢁ (see Figs. S5 and S6), along with the color
ꢁ
changes from violet to yellow for Fꢁ, from violet to colorless for AcOꢁ, H2PO4
,
ꢁ
ꢁ
ꢁ
HSO4 or Cl . However, less significant spectral and color changes of receptor 1
were observed after adding various common anions (i.e., Fꢁ, Clꢁ, Brꢁ, Iꢁ, AcOꢁ,
H2PO4ꢁ, HSO4 and ClO4ꢁ) in MeCN/H2O (1:1, v/v) mixture system. The results
ꢁ
showed that the presences of common anions have no effect on the selective
colorimetric detection of receptor 1 for Cys/Hcy in MeCN/H2O (1:1, v/v) under
neutral physiological conditions. Moreover, the tests indicated that receptor 1
is very sensitive to the basic environment in MeCN/H2O (1:1, v/v) (see Fig. S7),
therefore, the colorimetric detections of Cys/Hcy were carried out under
neutral buffer solution system, similar to physiological environment.
22. (a) Thiagarajan, V.; Ramamurthy, P.; Thirumalai, D.; Ramakrishnan, V. T. Org.
Lett. 2005, 7, 657; (b) Senthilvelan, A.; Ho, I. T.; Chang, K. C.; Lee, G. H.; Liu, Y.
H.; Chung, W. S. Chem. Eur. J. 2009, 15, 6152.