Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Highly Selective and Sensitive Detection of Fe3+ by 1,8-Naphthalimide-Based Fluorescent Sensors
Corresponding Author(s) : Dongmei Xu
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
Highly selective and sensitive detection of Fe3+ by two 1,8-naphthalimide-based fluorescent sensors, 2-(2-(dimethylamino)ethyl)-6-((2-(dimethylamino)ethyl)-amino)-1H-benzo[ de]isoquinoline-1,3(2H)-dione (MMN) and 2-(2-(diethylamino)ethyl)-6-((2-(diethylamino)-ethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione (EEN) in N,N-dimethyl formamide is reported. The fluorescence intensity of MMN and EEN is greatly enhanced by Fe3+ ion with the response time of less than 1s. The maximum fluorescence intensity of the sensors is linearly dependent on the concentration of Fe3+ within the range of 10-100 μM. The binding stoichiometry indicates that a 2:1 complex is formed between Fe3+ and the sensor and the detection limits for MMN and EEN are 180 and 310 nM, respectively. A large number of biologically relevant ions show no obvious interferences with the detection.
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- J. Han and K. Burgess, Chem. Rev., 110, 2709 (2010).
- X. Qian, X. Yi, Y. Xu, X. Guo, J. Qian and W. Zhu, Chem. Commun., 46, 6363 (2010).
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- Y. Hu, B. Wang and Z. Su, Polym. Int., 57, 1343 (2008).
- Q. Meng, X. Zhang, C. He and P. Zhou, Talanta, 84, 53 (2011).
- M. Kumar, N. Kumar and V. Bhalla, Org. Lett., 13, 1423 (2011).
- X. Guo, X. Qian and L. Jia, J. Am. Chem. Soc., 126, 2272 (2004).
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- X.F. Wei, H.Y. Yuan and D. Xiao, Chem. Res. Appl., 1, 85 (2009).
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- S. Smanmo, W. Nasomphan and P. Tangboriboonrat,Inorg. Chem. Commun., 14, 351 (2011).
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- W. Lin, L. Yuan, J. Feng and X. Cao, Eur. J. Org. Chem., 2689 (2008).
- T. Gao and S. Yang, Toxicol. Environ. Health Sci., 2, 73 (2010).
- B. Wang, J. Hai, Z. Liu, Q. Wang, Z. Yang and S. Sun, Angew. Chem., 122, 4680 (2010).
- L. Zhang, J. Wang, J. Fan, K. Guo and X. Peng, Bioorg. Med. Chem. Lett., 21, 5413 (2011).
- W. Lin, L. Long, L. Yuan, Z. Cao and J. Feng, Anal. Chim. Acta., 634, 262 (2009).
- L.A. Jones, C.T. Joyner, H.K. Kim and R.A. Kyff, Can. J. Chem., 48, 3132 (1970).
- I. Antonini, R. Volpini, D.D. Ben, C. Lambertucci and G. Cristalli, Bioorg. Med. Chem., 16, 8440 (2008).
- J. Zhang, R.J. Woods, P.B. Brown, R.A. Mowery, R.R. Kane, R.W. Jackson and F. Pollo, J. Biomed. Opt., 9, 1089 (2004).
- V.B. Bojinov, A.I. Venkova and N.I. Georgiev, Sens. Actuators B, 143, 42 (2009).
- G. Zong and G. Lu, Sens. Actuators B, 133, 617 (2008).
- B.P. Joshi, J. Park, W.I. Lee and K.-H. Lee, Talanta, 78, 903 (2009).
References
J. Han and K. Burgess, Chem. Rev., 110, 2709 (2010).
X. Qian, X. Yi, Y. Xu, X. Guo, J. Qian and W. Zhu, Chem. Commun., 46, 6363 (2010).
L. Cui, Y. Zhang, W. Zhu, Y. Xu, Q. Du, X. Wang, X. Qian and Y. Xiao, Org. Lett., 13, 928 (2011).
J.F. Zhang, C.S. Lim, S. Bhuniya, B.R. Cho and J.S. Kim, Org. Lett., 13, 1190 (2011).
R.M. Duke and T. Gunnlaugsson, Tetrahedron Lett., 52, 1503 (2011).
Z. Li, C. Niu, G. Zeng, Y. Liu, P. Gao, G. Huang and Y. Mao, Sens. Actuators B, 114, 308 (2006).
I.G. Nikolai, B.B. Vladimir and S.N. Peter, Dyes Pigments, 88, 350 (2011).
Z. Xu, X. Qian and J. Cui, Org. Lett., 7, 3029 (2005).
K.A. Mitchell, R.G. Brown, D. Yuan, S.-C. Chang, R. E. Utecht and D. E. Lewis, J. Photochem. Photobiol. A, 115, 157 (1998).
Y. Hu, B. Wang and Z. Su, Polym. Int., 57, 1343 (2008).
Q. Meng, X. Zhang, C. He and P. Zhou, Talanta, 84, 53 (2011).
M. Kumar, N. Kumar and V. Bhalla, Org. Lett., 13, 1423 (2011).
X. Guo, X. Qian and L. Jia, J. Am. Chem. Soc., 126, 2272 (2004).
T. Gunnlaugsson, T.C. Lee and R. Parkesh, Org. Biomol. Chem., 1, 3265 (2003).
S.Y. Kim and J.-I. Hong, Tetrahedron Lett., 50, 2822 (2009).
Y.X. Yang, X.R. Deng, X.Y. Ji, L.J. Qin and Z. Sun, Chem. J. Chin. Univ., 5, 919 (2008).
C.R. Lohani, J.-M. Kim and K.-H. Lee, Bioorg. Med. Chem. Lett., 19, 6069 (2009).
W.H. Peng, X.N. An and X.J. Zhu, Chem. Reagents, 6, 427 (2009).
Y.M. Ma and R.C. Hider, Bioorg. Med. Chem., 17, 8093 (2009).
X.F. Wei, H.Y. Yuan and D. Xiao, Chem. Res. Appl., 1, 85 (2009).
S. Fakih, M. Podinovskaia, X.-L. Kong, U.E. Schaible, H.L. Collins and R.C. Hider, J. Pharm. Sci., 98, 2212 (2009).
Q. Zhang, Y.-W. Sha and J.-H. Wang, Molecules, 15, 2962 (2010).
D.Y. Lee, N. Singh and D.O. Jang, Tetrahedron Lett., 52, 1368 (2011).
S. Smanmo, W. Nasomphan and P. Tangboriboonrat,Inorg. Chem. Commun., 14, 351 (2011).
D. Staneva, I. Grabchev, J.-P. Soumillion and V. Bojinov, J. Photochem. Photobiol. A, 189, 192 (2007).
W. Lin, L. Yuan, J. Feng and X. Cao, Eur. J. Org. Chem., 2689 (2008).
T. Gao and S. Yang, Toxicol. Environ. Health Sci., 2, 73 (2010).
B. Wang, J. Hai, Z. Liu, Q. Wang, Z. Yang and S. Sun, Angew. Chem., 122, 4680 (2010).
L. Zhang, J. Wang, J. Fan, K. Guo and X. Peng, Bioorg. Med. Chem. Lett., 21, 5413 (2011).
W. Lin, L. Long, L. Yuan, Z. Cao and J. Feng, Anal. Chim. Acta., 634, 262 (2009).
L.A. Jones, C.T. Joyner, H.K. Kim and R.A. Kyff, Can. J. Chem., 48, 3132 (1970).
I. Antonini, R. Volpini, D.D. Ben, C. Lambertucci and G. Cristalli, Bioorg. Med. Chem., 16, 8440 (2008).
J. Zhang, R.J. Woods, P.B. Brown, R.A. Mowery, R.R. Kane, R.W. Jackson and F. Pollo, J. Biomed. Opt., 9, 1089 (2004).
V.B. Bojinov, A.I. Venkova and N.I. Georgiev, Sens. Actuators B, 143, 42 (2009).
G. Zong and G. Lu, Sens. Actuators B, 133, 617 (2008).
B.P. Joshi, J. Park, W.I. Lee and K.-H. Lee, Talanta, 78, 903 (2009).