3430
J. Li et al. / Polymer 51 (2010) 3425e3430
[6] Izuhara D, Swager TM. J Am Chem Soc 2009;131:17724e5.
[7] Tan C, Pinto MR, Schanze KS. Chem Commun 2002;5:446e7.
[8] Tan C, Atas E, Muller JG, Pinto MR, Kleiman VD, Schanze KS. J Am Chem Soc
2004;126:13685e94.
(Lewis acid cation) in solution, the HOMO of the receptor is low-
ered. This decreases the driving force for the PET process and can
turn on the fluorescence of the fluorophore.
[9] Pinto MR, Kristal BM, Schanze KS. Langmuir 2003;19:6523e33.
[10] Zhou Q, Swager TM. J Am Chem Soc 1995;117:12593e602.
[11] Chen L, McBranch DW, Wang HL, Helgeson R, Wudl F, Whitten DG. Proc Natl
Acad Sci U S A 1999;96:12287e92.
The fluorescence response behaviors of P-2 on other various
metal ions were also examined under the same conditions as Hg2þ
ion determination (Fig. 7). As a result, the fluorescence enhance-
ment degree (F/F0 ꢂ 1) of the polymer P-2 is 1.0, 3.0, 18.5, 24.3, 2.8,
ꢂ8.0, 1.0, 2.7, ꢂ7.6 and 1.9% by Kþ, Mg2þ, Pb2þ, Co2þ, Ni2þ, Agþ,
Cd2þ, Cu2þ, Fe3þ and Zn2þ upon the 1:5 molar ratio addition of
a metal salt solution, respectively. The results indicate that P-2 can
exhibit excellent selectivity in sensing Hg2þ. For Hg2þ detection,
one of the essential requirements is minor or no interference from
other metal ions. The Hg2þ selective detection experiments of P-2
in water (1.0 ꢁ 10ꢂ5 mol Lꢂ1) were conducted in the presence of the
mixture of Kþ, Mg2þ, Pb2þ, Co2þ, Ni2þ, Cd2þ, Cu2þ, Fe3þ and Zn2þ
(Fig. 8) at 5.0 ꢁ 10ꢂ5 mol Lꢂ1 in water, respectively. Compared with
that containing both mixture ions and Hg2þ, the fluorescence
intensities of P-2 do not appear obvious change. Herein, the water-
soluble polymer P-2 is specifically sensitive toward Hg2þ, not
toward other metals, which can be attributed to strong HgeS
binding and coordination diversification of Hg2þ with the resulting
polymer. It can be concluded that this kind water-soluble poly-
electrolyte P-2 can be used as Hg2þ selective probe which could
hardly be affected by those coexistent ions.
[12] Harrison BS, Ramey MB, Reynolds JR, Schanze KS.
J Am Chem Soc
2000;122:8561e2.
[13] Wang DL, Gong X, Heeger PS, Rininsland F, Bazan GC, Heeger AG. Proc Natl
Acad Sci U S A 2002;99:49e53.
[14] Kumaraswamy S, Bergstedt T, Shi XB, Rininsland F, Kushon S, Xia WS, et al.
Proc Natl Acad Sci U S A 2004;101:7511e5.
[15] Miranda OR, You CC, Phillips R, Kim IB, Ghosh PS, Bunz UHF, et al. J Am Chem
Soc 2007;129:9856e7.
[16] Jones RM, Bergstedt TS, McBranch DW, Whitten DG. J Am Chem Soc 2001;
123:6726e7.
[17] Kushon SA, Ley KD, Bradford K, Jones RM, McBranch D, Whitten D. Langmuir
2002;18:7245e9.
[18] Pu KY, Liu B. Adv Funct Mater 2009;19:277e84.
[19] Pu KY, Cai L, Liu B. Macromolecules 2009;42:5933e40.
[20] Pu KY, Liu B. Macromolecules 2008;41:6636e40.
[21] Fang Z, Pu KY, Liu B. Macromolecules 2008;41:8380e7.
[22] McQuade DT, Pullen AE, Swager TM. Chem Rev 2000;100:2537e74.
[23] Thomas III SW, Joly GD, Swager TM. Chem Rev 2007;107:1339e86.
[24] Zhang Z, Wu D, Guo X, Qian X, Lu Z, Zu Q, et al. Chem Res Toxicol
2005;18:1814e20.
[25] Grandjean P, Weihe P, White RF, Debes F. Environ Res 1998;77:165e72.
[26] Boening DW. Chemosphere 2000;40:1335e51.
[27] Harris HH, Pickering IJ, George GN. Science 2003;301:1203.
[28] Nolan EM, Lippard SJ. Chem Rev 2008;108:3443e80.
[29] Kim IB, Dunkhorst A, Gilbert J, Bunz UHF. Macromolecules 2005;38:4560e2.
[30] Fan LJ, Jones WE. J Am Chem Soc 2006;128:6784e5.
[31] Fan LJ, Zhang Y, Jones WE. Macromolecules 2005;38:2844e9.
[32] Kim IB, Bunz UHF. J Am Chem Soc 2006;128:2818e9.
[33] Liu X, Tang Y, Wang L, Zhang J, Song S, Fan C, et al. Adv Mater 2007;
19:1471e4.
[34] Tang Y, He F, Yu M, Feng F, An L, Sun H, et al. Macromol Rapid Commun
2006;27:389e92.
[35] Li C, Zhou C, Zheng H, Yin X, Zou Z, Liu H, et al. J Polym Sci Part A Polym Chem
2008;46:1998e2007.
[36] Huang XB, Meng J, Dong Y, Cheng YX, Zhu CJ. J Polym Sci Part A Polym Chem
2010;48:997e1006.
[37] Zheng LF, Huang XB, Shen YG, Cheng YX. Synlett 2010;3:453e6.
[38] de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP,
Rademacher JT, et al. Chem Rev 1997;97:1515e66.
4. Conclusion
A new fluorometric probe for detecting Hg2þ in aqueous solu-
tion based on the water-soluble conjugated polyelectrolyte P-2,
which exhibits a very high selectivity over other interfering cations,
has been developed. P-2 was obtained by quaternization of P-1
which was synthesized by Pd-catalyzed Sonogashira reaction. The
result has shown that the water-soluble polyelectrolyte P-2 can be
used as Hg2þ selective probe which could hardly be affected by
those coexistent ions in aqueous solution.
[39] Chen Y, Pu KY, Fan QL, Qi XL, Huang YQ, Lu XM, et al. J Polym Sci Part A Polym
Chem 2009;47:5057e67.
Acknowledgements
[40] Balamurugan A, Reddy MLP, Jayakannan M. J Polym Sci Part A Polym Chem
2009;47:5144e57.
[41] Ros-Lis JY, Marcos MD, Mártinez-Máñez R, Rurack K, Soto J. Angew Chem Int
Ed 2005;44:4405e7.
[42] Yang YK, Yook KJ, Tae J. J Am Chem Soc 2005;127:16760e1.
[43] Nolan EM, Lippard SJ. J Am Chem Soc 2003;125:14270e1.
[44] Prodi L, Bargossi C, Montalti M, Zaccheroni N, Su N, Bradshaw JS, et al. J Am
Chem Soc 2000;122:6769e70.
This work was supported by the National Natural Science
Foundation of China (No. 20774042) and National Basic Research
Program of China (2010CB923303).
Appendix. Supplementary data
[45] Tang B, Ding B, Xu K, Tong L. Chem Eur J 2009;15:3147e51.
[46] Wu JS, Hwang IC, Kim KS, Kim JS. Org Lett 2007;9:907e10.
[47] Lee MH, Wu JS, Lee JW, Jung JH, Kim JS. Org Lett 2007;9:2501e4.
[48] Ko SK, Yang YK, Tae J, Shin I. J Am Chem Soc 2006;128:14150e5.
[49] Nolan EM, Lippard SJ. J Am Chem Soc 2007;129:5910e8.
[50] Huang XB, Xu Y, Zheng LF, Meng J, Cheng YX. Polymer 2009;50:5996e6000.
[51] Neto BAD, Lopes AS, Ebeling G, Gonçalves RS, Costa VEU, Quina FH, et al.
Tetrahedron 2005;61:10975e82.
Supplementary data associated with this article can be found in
References
[52] Liu SJ, Fang C, Zhao Q, Fan QL, Huang W. Macromol Rapid Commun 2008;
29:1212e5.
[1] Pinto MR, Schanze KS. Synthesis 2002;9:1293e309.
[2] Jiang H, Taranekar P, Reynolds JR, Schanze KS. Angew Chem Int Ed 2009;
48:4300e16.
[53] Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett 1975;16:4467e70.
[54] Chinchilla R, Nájera C. Chem Rev 2007;107:874e922.
[55] Liu B, Yu W, Lai YH, Huang W. Chem Commun; 2000:551e2.
[56] Rurack K, Kollmannsberger M, Resch-Genger U, Daub J. J Am Chem Soc
2000;122:968e9.
[3] Hoven CV, Garcia A, Bazan GC, Nguyen TQ. Adv Mater 2008;20:3793e810.
[4] Dwight SJ, Gaylord BS, Hong JW, Bazan GC.
J Am Chem Soc 2004;
126:16850e9.
[5] Chen LH, Xu S, McBranch D, Whitten DJ. J Am Chem Soc 2000;122:9302e3.