R. Kretzschmar, Environ. Sci. Technol., 2005, 39, 6616–6623;
(
d) J. B. Chen, J. Gaillardet and P. Louvat, Environ. Sci. Technol.,
008, 42, 6494–6501; (e) A. Coskun, E. Deniz and E. U. Akkaya,
2
Org. Lett., 2005, 7, 5187–5189; (f) A. Saha, S. Manna and
A. K. Nandi, Soft Matter, 2009, 5, 3992–3996; (g) D. C. Magri,
New J. Chem., 2009, 33, 457–461.
2
(a) E. Tomat and S. J. Lippard, Curr. Opin. Chem. Biol., 2010, 14,
2
25–230; (b) N. Singh, N. Kaur, R. C. Mulrooney and J. F. Callan,
Tetrahedron Lett., 2008, 49, 6690–6692; (c) Z. P. Liu, C. L. Zhang,
W. J. He, Z. H. Yang, X. Gao and Z. J. Guo, Chem. Commun.,
2
010, 46, 6138–6140; (d) E. Tomat, E. M. Nolan, J. Jaworski and
S. J. Lippard, J. Am. Chem. Soc., 2008, 130, 15776–15777;
e) K. Komatsu, Y. Urano, H. Kojima and T. Nagano, J. Am.
(
Chem. Soc., 2007, 129, 13447–13454.
3
(a) H. Torii, M. Nakadai, K. Ishihara, S. Saito and H. Yamamoto,
Angew. Chem., Int. Ed., 2004, 43, 1983–1986; (b) P. Renzi,
J. Overgaard and M. Bella, Org. Biomol. Chem., 2010, 8,
Fig. 4 UV-vis spectra of the multicomponent sensory system with
2+
increasing amounts of Mg
(0–0.50 equiv.). Inset: 260–360 nm
9
80–983; (c) J. G. Hernandez and E. Juaristi, J. Org. Chem.,
spectral regions of the UV absorption.
2011, 76, 1464–1467; (d) B. J. Bench, C. M. Liu, C. R. Evett and
C. M. H. Watanabe, J. Org. Chem., 2006, 71, 9458–9463;
(e) K. Akagawa, S. Sakamoto and K. Kudo, Synlett, 2011, 6,
817–820; (f) J. W. Yang, C. Chandler, M. Stadler, D. Kampen and
B. List, Nature, 2008, 452, 453–455; (g) B. List, Tetrahedron, 2002,
To further understand the fluorescence behavior of this
multicomponent sensory system, UV-vis titration was conducted
2
+
with increasing amount of Mg
in CH CN (Fig. 4). the
3
5
8, 5573–5590.
UV-vis spectrum of 3 shows a maximal absorption at 316
4
(a) Y. Wang, L. T. Xu and D. W. Ma, Chem.–Asian J., 2010, 5,
74–76; (b) W. Zhu and D. W. Ma, J. Org. Chem., 2005,
and 280 nm. The absorbance peak at 316 nm shows obvious
2
+
reduction with increasing amount of Mg in the multi-
component system (1.0 eq 3 + 1.0 eq L-proline + 1.0 eq
7
0, 2696–2700; (c) D. W. Ma, Y. D. Zhang, J. C. Yao,
S. H. Wu and F. G. Tao, J. Am. Chem. Soc., 1998, 120,
2459–12467.
1
+
2+
Na + X eq Mg ), which can be attributed to the reorgan-
ization of this dynamic system. Moreover, one isosbestic point
at 259 nm is observed in the absorption spectra, which
indicates a stable complex formation in this system.
5
6
(a) J. R. Nitschke, Nature, 2009, 462, 736–738; (b) S. Ulrich and
J. M. Lehn, Chem.–Eur. J., 2009, 15, 5640–5645; (c) R. F. Ludlow
and S. Otto, Chem. Soc. Rev., 2008, 37, 101–108.
(a) E. H. C. Bromley, R. B. Sessions, A. R. Thomson and
D. N. Woolfson, J. Am. Chem. Soc., 2009, 131, 928–930;
In summary, a host molecule (3) can be employed for highly
(
b) R. Caraballo, H. Dong, J. P. Ribeiro, J. Jimenez-Barbero
and O. Ramstrom, Angew. Chem., Int. Ed., 2010, 49, 589–593;
c) P. K. Muller-Graff, H. Szelke, K. Severin and R. Kramer, Org.
2
+
sensitive and selective detection on Mg while L-proline acts
as a promoter in a multicomponent sensory system. This is the
first report on the promoting effect of L-proline in a fluorescence
(
Biomol. Chem., 2010, 8, 2327–2331.
(a) A. Buryak and K Severin, Angew. Chem., Int. Ed., 2005, 44,
7
8
2
+
sensory system. In this dynamic interactive system, Mg
7
935–7938; (b) A. Herrmann, Org. Biomol. Chem., 2009, 7,
3195–3204; (c) J. M. Lehn, Chem. Soc. Rev., 2007, 36, 151–160;
d) R. A. R. Hunt and S. Otto, Chem. Commun., 2011, 47, 847–858.
(a) H. Rubin, Arch. Biochem. Biophys., 2007, 458, 16–23;
b) J. A. Cowan, BioMetals, 2002, 15, 225–235; (c) O. B. Stepura
and A. I. Martynow, Int. J. Cardiol., 2009, 134, 145–147;
(d) S. C. Larsson, M. J. Virtanen, M. Mars, S. Mannisto
P. Pietinen, D. Albanes and J. Virtamo, Arch. Intern. Med.,
008, 168, 459–465.
could be distinguished easily through the most pronounced
fluorescence enhancement response as well as a large blue shift
from other cations. Most importantly, the multicomponent
sensory system displays bright green fluorescence color in the
(
(
2
+
presence of Mg
under a commercially available UV lamp
¨
¨
,
(
l = 365 nm), which can be identified by the naked eye.
This work was supported by the National Natural Science
2
9
A. Kulkarni, S. A. Patil and P. S. Badami, Eur. J. Med. Chem.,
2009, 44, 2904–2912.
Foundation of China (No. 20832001, 21074054) and
National Basic Research Program of China (2007CB925103,
10 (a) Y. Zhang, X. F. Guo, W. X. Si, L. H. Jia and X. H. Qian, Org.
Lett., 2008, 10, 473–476; (b) Z. P. Liu, C. L. Zhang, Y. L. Li,
Z. Y. Wu, F. Qian, X. L. Yang, W. J. He, X. Gao and Z. J. Guo,
Org. Lett., 2009, 11, 795–798; (c) Y. W. Wang, M. X. Yu,
Y. H. Yu, Z. P. Bai, Z. Shen, F. Y. Li and X. Z. You, Tetrahedron
Lett., 2009, 50, 6169–6172.
2
010CB923303).
Notes and references
1
(a) S. F. Sousa, P. A. Fernandes and M. J. Ramos, J. Am. Chem.
Soc., 2007, 129, 1378–1385; (b) D. D. Mott, M. Benveniste and
R. J. Dingledine, J. Neurosci., 2008, 28, 1659–1671;
11 (a) N. Giuseppone and J. M. Lehn, J. Am. Chem. Soc., 2004, 126,
11448–11449; (b) J. M. Lehn, Science, 2002, 295, 2400–2403;
(c) M. Barboiu, Chem. Commun., 2010, 46, 7466–7476.
(c) A. Voegelin, S. Pfister, A. C. Scheinost, M. A. Marcus and
9
452 Chem. Commun., 2011, 47, 9450–9452
This journal is c The Royal Society of Chemistry 2011