Citation: Yao Liu, Er-Bing Yang, Rui Han, Di Zhang, Yong Ye, Yu-Fen Zhao. A new rhodamine-based fl uorescent chemosensor for mercury in aqueous media[J]. Chinese Chemical Letters, ;2014, 25(7): 1065-1068. doi: 10.1016/j.cclet.2014.04.033 shu

A new rhodamine-based fl uorescent chemosensor for mercury in aqueous media

Yao Liu ^a ,
Er-Bing Yang ^a ,
Rui Han ^a ,
Di Zhang ^a ,
Yong Ye ^a,b,, ,
Yu-Fen Zhao ^a,b,c

1.
a Phosphorus Chemical Engineering Research Center of Henan Province, the College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China;
2.
b Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100086, China;
c Key Lab Chem Biol, Fujian Prov.
c Key Lab Chem Biol, Fujian Prov. Coll. Chem. & Chem. Engn., Xiamen University, Xiamen 361005, China

Corresponding author: Yong Ye,
Received Date: 11 November 2013
Available Online: 22 April 2014
Fund Project: This work was financially supported by the National Natural Science Foundation of China (Nos. 20972143, 21375113) (Nos. 20972143, 21375113)Program for New Century Excellent Talents in University (No. NCET-11-0950). (No. NCET-11-0950)

A new fluorescent "on-off" chemosensor for Hg²⁺ initiated by a derivative of rhodamine B was designed and synthesized. Compound 1 exhibited high sensitivity and selectivity for Hg²⁺ over other commonly coexistent metal ions in aqueous media. Upon the addition of Hg²⁺, the spirocyclic ring of probe is opened and a significant enhancement of visible color and fluorescence in the range of 500-600 nm is observed. The colorimetric and fluorescent response to Hg²⁺ can be conveniently detected by the naked eye, which provides a facile method for visual detection of Hg²⁺. From the molecular structure and spectral results of 1, an irreversible, hydrolysis, desulfurization reaction mechanism is proposed.
- Fluorescent probe,
- Rhodamine,
- Mercury,
- On-off,
- Chemosensor
1. [1]
  [1] (a) J.F. Callan, A.P. de Silva, D.C. Magri, Luminescent sensors and switches in the early 21st century, Tetrahedron 61 (2005) 8551-8588; (b) A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, P.L.M. Lynch, Molecular photoionic switches with an internal reference channel for fluorescent pH sensing applications, New J. Chem. 20 (1996) 871-880; (c) F. Pina, M.A. Bernardo, E. Garcia-Espana, Fluorescent chemosensors containing polyamine receptors, Eur. J. Inorg. Chem. 2000 (2000) 2143-2157; (d) K. Rurack, U. Resch-Genger, Rigidization, preorientation and electronic decoupling-the ‘magic triangle' for the design of highly efficient fluorescent sensors and switches, Chem. Soc. Rev. 31 (2002) 116-127; (e) B. Valeur, I. Leray, Design principles of fluorescent molecular sensors for cation recognition, Coord. Chem. Rev. 205 (2000) 3-40.
2. [2]
  [2] (a) R.Q. Zhou, B.J. Li, N.J. Wu, et al., Cyclen-functionalized perylenebisimides as sensitive and selective fluorescent sensors for Pb²⁺ in aqueous solution, Chem. Commun. 47 (2011) 6668-6670; (b) Q. Liu, G.P. Li, D.J. Zhu, L. Xue, H. Jiang, Design of quinoline-based fluorescent probe for the ratiometric detection of cadmium in aqueous media, Chin. Chem. Lett. 24 (2013) 479-482; (c) J. Liu, Q. Lin, H. Yao, et al., Turn-on fluorescence sensing of cyanide ions in aqueous solution, Chin. Chem. Lett. 25 (2014) 35-38.
3. [3]
  [3] (a) J.J. Du, J.L. Fan, X.J. Peng, et al., A new fluorescent chemodosimeter for Hg²⁺: selectivity, sensitivity, and resistance to Cys and GSH, Org. Lett. 12 (2010) 476-479; (b) S. Voutsadaki, G.K. Tsikalas, E. Klontzas, G.E. Froudakis, H.E. Katerinopoulos, A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media, Chem. Commun. 46 (2010) 3292-3294; (c) V. Bhalla, R. Tejpal, M. Kumar, Rhodamine appended terphenyl: a reversible "off-on" fluorescent chemosensor for mercury ions, Sens. Actuators B 151 (2010) 180-185.
4. [4]
  [4] (a) Y.K. Yang, K.J. Yook, J. Tae, A rhodamine-based fluorescent and colorimetric chemodosimeter for the rapid detection of Hg²⁺ ions in aqueous media, J. Am. Chem. Soc. 127 (2005) 16760-16761; (b) J.Y. Kwon, Y.J. Jang, Y.J. Lee, et al., A highly selective fluorescent chemosensor for Pb²⁺, J. Am. Chem. Soc. 127 (2005) 10107-10111; (c) L. Tang, Y. Li, R. Nandhakumar, J. Qian, An unprecedented rhodamine-based fluorescent and colorimetric chemosensor for Fe³⁺ in aqueous media, Monatsh. Chem. 141 (2010) 615-620.
5. [5]
  [5] (a) R. Han, X. Yang, D. Zhang, et al., A bis(rhodamine)-based highly sensitive and selective fluorescent chemosensor for Hg(II) in aqueous, media, New J. Chem. 36 (2012) 1961-1965; (b) W.Y. Lin, X.W. Cao, Y.D. Ding, L. Yuan, L.L. Long, A highly selective and sensitive fluorescent probe for Hg²⁺ imaging in live cells based on a rhodamine-thioamidealkyne scaffold, Chem. Commun. 46 (2010) 3529-3531; (c) Z.X. Han, B.S. Zhu, T.L. Wu, et al., A fluorescent probe for Hg²⁺ sensing in solutions and living cells with a wide working pH range, Chin. Chem. Lett. 25 (2014) 73-76.
6. [6]
  [6] (a) D. Zhang, M. Wang, M. Chai, et al., Three highly sensitive and selective colorimetric and off-on fluorescent chemosensors for Cu²⁺ in aqueous solution, Sens. Actuators B 168 (2012) 200-206; (b) X. Chen, H. Hong, R. Han, et al., A new bis(rhodamine)-based fluorescent chemosensor for Fe³⁺, J. Fluoresc. 22 (2012) 789-794.
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