Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Spectral Studies of Schiff Base Receptor for Fluorescence Detection of Hg(II)
Corresponding Author(s) : Chinnadurai Anbuselvan
Asian Journal of Chemistry,
Vol. 31 No. 3 (2019): Vol 31 Issue 3
Abstract
In this study, a fluorescent film probe with a structure centered on a Schiff base viz. (N1′,N2′)-N1,N2-bis(2-amino-3,5-dibromobenzylidene)-1,2-diamine (DAB) was synthesized. The probe was used as a fluorescence chemosensor for transition metal ion detection in an aqueous medium. Fluorescence was measured through fluorescence spectroscopy, and the emission maximum of the proposed sensor was 552 nm. Furthermore, the proposed film sensor exhibited a high sensitivity and selectivity toward Hg2+ ions. The limit of detection (LOD) of chemosensor, which was calculated using the fluorescence titration method, found to be 2.11 μM at 552 nm. The fluorescence spectroscopic data evidenced the potential of the proposed sensor for application in the detection and determination of Hg2+ ions in deionized water without the interference from other metal ions.
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- B.M. Ahmed, N.A. Rudell, I. Soto and G. Mezei, J. Org. Chem., 82, 10549 (2017); https://doi.org/10.1021/acs.joc.7b02070.
- R.M. Clarke and T. Storr, Dalton Trans., 43, 9380 (2014); https://doi.org/10.1039/C4DT00591K.
- R. Vadivel, R. Jayakumar and N. Ananthi, Org. Med. Chem., 5, 555662 (2018); https://doi.org/10.19080/OMCIJ.2018.05.555662.
- U.M. Rafi, D. Mahendiran, A.K. Haleel, R.P. Nankar, M. Doble and A.K. Rahiman, New J. Chem., 40, 2451 (2016); https://doi.org/10.1039/C5NJ02739J.
- A.A. Shanty and P.V. Mohanan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 192, 181 (2017); https://doi.org/10.1016/j.saa.2017.11.019.
- K. Shalini, N. Kumar, S. Drabu and P.K. Sharma, Beilstein J. Org. Chem., 7, 668 (2011); https://doi.org/10.3762/bjoc.7.79.
- M.A. Mokhles and A.L. Ammar, J. Appl. Sci. (Faisalabad), 5, 85 (2016).
- K.V. Shuvaev, L.N. Dawe and L.K. Thompson, Eur. J. Inorg. Chem., 4583 (2010); https://doi.org/10.1002/ejic.201000837.
- Y.-C. Duan, Y.-C. Ma, E. Zhang, X.-J. Shi, M.-M. Wang, X.-W. Ye and H.-M. Liu, Eur. J. Med. Chem., 62, 11 (2013); https://doi.org/10.1016/j.ejmech.2012.12.046.
- C. Chandramouli, M.R. Shivanand, T.B. Nayanbhai, B. Bheemachari and R.H. Udupi, J. Chem. Pharm. Res., 4, 151 (2012).
- R.P. Chinnasamy, R. Sundararajan and S. Govindaraj, J. Adv. Pharm. Technol. Res., 1, 342 (2010); https://doi.org/10.4103/0110-5558.72428.
- K.M. Abuamer, A.A. Maihub, M.M. El-Ajaily, A.M. Etorki, M.M. AbouKrisha and M.A. Almagani, Int. J. Org. Chem., 4, 7 (2014); https://doi.org/10.4236/ijoc.2014.41002.
- M. Sunita, M. Padmaja, B. Anupama and C.G. Kumari, J. Fluoresc., 22, 1003 (2012); https://doi.org/10.1007/s10895-012-1038-0.
- C.J. Hua, H. Zheng, K. Zhang, M. Xin, J.R. Gao and Y.J. Li, Tetrahedron, 72, 8365 (2016); https://doi.org/10.1016/j.tet.2016.08.023.
- C. Sun, J. Sun, F. Qiu, W. Li, Z. Chang and L. Zhang, Spectrochim. Acta A Mol. Biomol. Spectrosc., 188, 1 (2018); https://doi.org/10.1016/j.saa.2017.06.061.
- Y. Wang, Z. Liu, J. Sun, X. Liu, M. Pei and G. Zhang, J. Photoch. Photobiol. A, 332, 515 (2017); https://doi.org/10.1016/j.jphotochem.2016.10.004.
- Q. Long, Y. Wen, H. Li, Y. Zhang and S. Yao, J. Fluoresc., 27, 205 (2017); https://doi.org/10.1007/s10895-016-1947-4.
- X. Cheng, Y. Yu, Y. Jia and L. Duan, Mater. Des., 95, 133 (2016); https://doi.org/10.1016/j.matdes.2016.01.103.
- J. Wei, J. Ren, J. Liu, X. Meng, X. Ren, Z. Chen and F. Tang, Biosens. Bioelectron., 52, 304 (2014); https://doi.org/10.1016/j.bios.2013.09.006.
- A.K. Dwivedi, G. Saikia and P.K. Iyer, J. Mater. Chem., 21, 2502 (2011); https://doi.org/10.1039/C0JM03054F.
- X. Wu, B. Xu, H. Tong and L. Wang, Macromolecules, 43, 8917 (2010); https://doi.org/10.1021/ma1019413.
- O. Brümmer, J.J. La Clair and K.D. Janda, Bioorg. Med. Chem., 9, 1067 (2001); https://doi.org/10.1016/S0968-0896(01)00049-9.
- J.M. Benoit, W.F. Fitzgerald and A.W. Damman, Environ. Res., 78, 118 (1998); https://doi.org/10.1006/enrs.1998.3850
- Mercury Update: Impact on Fish Advisories; EPA Fact Sheet EPA823-F-01-001; Environmental Protection Agency, Office of Water: Washington, DC, 2001.
- S.K. Pandey, K.H. Kim and R.J.C. Brown, TrAC Trends Analyt. Chem., 30, 899 (2011); https://doi.org/10.1016/j.trac.2011.01.017.
- B. Dimitrova, K. Benkhedda, E. Ivanova and F. Adams, J. Anal. At. Spectrom., 19, 1394 (2004); https://doi.org/10.1039/b407546n.
- C. Locatelli, D. Melucci and G. Torsi, Anal. Bioanal. Chem., 382, 1567 (2005); https://doi.org/10.1007/s00216-005-3356-4.
- K. Van Meel, A. Smekens, M. Behets, P. Kazandjian and R. Van Grieken, Anal. Chem., 79, 6383 (2007); https://doi.org/10.1021/ac070815r.
- L. Duan, Y. Xu and X. Qian, Chem. Commun., 6339 (2008); https://doi.org/10.1039/b815298e.
- J.S. Kim and D.T. Quang, Chem. Rev., 107, 3780 (2007); https://doi.org/10.1021/cr068046j.
- H.N. Kim, W.X. Ren, J.S. Kim and J. Yoon, Chem. Soc. Rev., 41, 3210 (2012); https://doi.org/10.1039/C1CS15245A.
- X. Guo, X. Qian and L. Jia, J. Am. Chem. Soc., 126, 2272 (2004); https://doi.org/10.1021/ja037604y.
- S.Y. Moon, N.R. Cha, Y.H. Kim and S. Chang, J. Org. Chem., 69, 181 (2004); https://doi.org/10.1021/jo034713m.
- E.M. Nolan and S.J. Lippard, J. Am. Chem. Soc., 125, 14270 (2003); https://doi.org/10.1021/ja037995g.
- V. Dujols, F. Ford and A.W. Czarnik, J. Am. Chem. Soc., 119, 7386 (1997); https://doi.org/10.1021/ja971221g.
- T.-H. Kim and T.M. Swager, Angew. Chem. Int. Ed., 42, 4803 (2003); https://doi.org/10.1002/anie.200352075.
- C.A. Roeschlaub, N.L. Maidwell, M. Reza Rezai and P.G. Sammes, Chem. Commun., 1637 (1999); https://doi.org/10.1039/a904971a.
- M.-Y. Chae and A.W. Czarnik, J. Am. Chem. Soc., 114, 9704 (1992); https://doi.org/10.1021/ja00050a085.
- G. Zhang, D. Zhang, S. Yin, X. Yang, Z. Shuai and D. Zhu, Chem. Commun., 2161 (2005); https://doi.org/10.1039/b417952h.
- B. Liu and H. Tian, Chem. Commun., 3156 (2005); https://doi.org/10.1039/b501913c.
- K.C. Song, J.S. Kim, S.M. Park, K.-C. Chung, S. Ahn and S.-K. Chang, Org. Lett., 8, 3413 (2006); https://doi.org/10.1021/ol060788b.
- X. Zhang, Y. Xiao and X. Qian, Angew. Chem. Int. Ed., 47, 8025 (2008); https://doi.org/10.1002/anie.200803246.
- M. Kumar, R. Kumar and V. Bhalla, Chem. Commun., 7384 (2009); https://doi.org/10.1039/b914821c.
- V. Bhalla, Roopa, M. Kumar, P.R. Sharma and T. Kaur, Inorg. Chem., 51, 2150 (2012); https://doi.org/10.1021/ic201990q.
- M. Kumar, N. Kumar, V. Bhalla, P.R. Sharma and Y. Qurishi, Chem. Commun., 48, 4719 (2012); https://doi.org/10.1039/c2cc30932g.
- , V. Bhalla, M. Roopa and Kumar, Org. Lett., 14, 2802 (2012); https://doi.org/10.1021/ol301030z.
References
B.M. Ahmed, N.A. Rudell, I. Soto and G. Mezei, J. Org. Chem., 82, 10549 (2017); https://doi.org/10.1021/acs.joc.7b02070.
R.M. Clarke and T. Storr, Dalton Trans., 43, 9380 (2014); https://doi.org/10.1039/C4DT00591K.
R. Vadivel, R. Jayakumar and N. Ananthi, Org. Med. Chem., 5, 555662 (2018); https://doi.org/10.19080/OMCIJ.2018.05.555662.
U.M. Rafi, D. Mahendiran, A.K. Haleel, R.P. Nankar, M. Doble and A.K. Rahiman, New J. Chem., 40, 2451 (2016); https://doi.org/10.1039/C5NJ02739J.
A.A. Shanty and P.V. Mohanan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 192, 181 (2017); https://doi.org/10.1016/j.saa.2017.11.019.
K. Shalini, N. Kumar, S. Drabu and P.K. Sharma, Beilstein J. Org. Chem., 7, 668 (2011); https://doi.org/10.3762/bjoc.7.79.
M.A. Mokhles and A.L. Ammar, J. Appl. Sci. (Faisalabad), 5, 85 (2016).
K.V. Shuvaev, L.N. Dawe and L.K. Thompson, Eur. J. Inorg. Chem., 4583 (2010); https://doi.org/10.1002/ejic.201000837.
Y.-C. Duan, Y.-C. Ma, E. Zhang, X.-J. Shi, M.-M. Wang, X.-W. Ye and H.-M. Liu, Eur. J. Med. Chem., 62, 11 (2013); https://doi.org/10.1016/j.ejmech.2012.12.046.
C. Chandramouli, M.R. Shivanand, T.B. Nayanbhai, B. Bheemachari and R.H. Udupi, J. Chem. Pharm. Res., 4, 151 (2012).
R.P. Chinnasamy, R. Sundararajan and S. Govindaraj, J. Adv. Pharm. Technol. Res., 1, 342 (2010); https://doi.org/10.4103/0110-5558.72428.
K.M. Abuamer, A.A. Maihub, M.M. El-Ajaily, A.M. Etorki, M.M. AbouKrisha and M.A. Almagani, Int. J. Org. Chem., 4, 7 (2014); https://doi.org/10.4236/ijoc.2014.41002.
M. Sunita, M. Padmaja, B. Anupama and C.G. Kumari, J. Fluoresc., 22, 1003 (2012); https://doi.org/10.1007/s10895-012-1038-0.
C.J. Hua, H. Zheng, K. Zhang, M. Xin, J.R. Gao and Y.J. Li, Tetrahedron, 72, 8365 (2016); https://doi.org/10.1016/j.tet.2016.08.023.
C. Sun, J. Sun, F. Qiu, W. Li, Z. Chang and L. Zhang, Spectrochim. Acta A Mol. Biomol. Spectrosc., 188, 1 (2018); https://doi.org/10.1016/j.saa.2017.06.061.
Y. Wang, Z. Liu, J. Sun, X. Liu, M. Pei and G. Zhang, J. Photoch. Photobiol. A, 332, 515 (2017); https://doi.org/10.1016/j.jphotochem.2016.10.004.
Q. Long, Y. Wen, H. Li, Y. Zhang and S. Yao, J. Fluoresc., 27, 205 (2017); https://doi.org/10.1007/s10895-016-1947-4.
X. Cheng, Y. Yu, Y. Jia and L. Duan, Mater. Des., 95, 133 (2016); https://doi.org/10.1016/j.matdes.2016.01.103.
J. Wei, J. Ren, J. Liu, X. Meng, X. Ren, Z. Chen and F. Tang, Biosens. Bioelectron., 52, 304 (2014); https://doi.org/10.1016/j.bios.2013.09.006.
A.K. Dwivedi, G. Saikia and P.K. Iyer, J. Mater. Chem., 21, 2502 (2011); https://doi.org/10.1039/C0JM03054F.
X. Wu, B. Xu, H. Tong and L. Wang, Macromolecules, 43, 8917 (2010); https://doi.org/10.1021/ma1019413.
O. Brümmer, J.J. La Clair and K.D. Janda, Bioorg. Med. Chem., 9, 1067 (2001); https://doi.org/10.1016/S0968-0896(01)00049-9.
J.M. Benoit, W.F. Fitzgerald and A.W. Damman, Environ. Res., 78, 118 (1998); https://doi.org/10.1006/enrs.1998.3850
Mercury Update: Impact on Fish Advisories; EPA Fact Sheet EPA823-F-01-001; Environmental Protection Agency, Office of Water: Washington, DC, 2001.
S.K. Pandey, K.H. Kim and R.J.C. Brown, TrAC Trends Analyt. Chem., 30, 899 (2011); https://doi.org/10.1016/j.trac.2011.01.017.
B. Dimitrova, K. Benkhedda, E. Ivanova and F. Adams, J. Anal. At. Spectrom., 19, 1394 (2004); https://doi.org/10.1039/b407546n.
C. Locatelli, D. Melucci and G. Torsi, Anal. Bioanal. Chem., 382, 1567 (2005); https://doi.org/10.1007/s00216-005-3356-4.
K. Van Meel, A. Smekens, M. Behets, P. Kazandjian and R. Van Grieken, Anal. Chem., 79, 6383 (2007); https://doi.org/10.1021/ac070815r.
L. Duan, Y. Xu and X. Qian, Chem. Commun., 6339 (2008); https://doi.org/10.1039/b815298e.
J.S. Kim and D.T. Quang, Chem. Rev., 107, 3780 (2007); https://doi.org/10.1021/cr068046j.
H.N. Kim, W.X. Ren, J.S. Kim and J. Yoon, Chem. Soc. Rev., 41, 3210 (2012); https://doi.org/10.1039/C1CS15245A.
X. Guo, X. Qian and L. Jia, J. Am. Chem. Soc., 126, 2272 (2004); https://doi.org/10.1021/ja037604y.
S.Y. Moon, N.R. Cha, Y.H. Kim and S. Chang, J. Org. Chem., 69, 181 (2004); https://doi.org/10.1021/jo034713m.
E.M. Nolan and S.J. Lippard, J. Am. Chem. Soc., 125, 14270 (2003); https://doi.org/10.1021/ja037995g.
V. Dujols, F. Ford and A.W. Czarnik, J. Am. Chem. Soc., 119, 7386 (1997); https://doi.org/10.1021/ja971221g.
T.-H. Kim and T.M. Swager, Angew. Chem. Int. Ed., 42, 4803 (2003); https://doi.org/10.1002/anie.200352075.
C.A. Roeschlaub, N.L. Maidwell, M. Reza Rezai and P.G. Sammes, Chem. Commun., 1637 (1999); https://doi.org/10.1039/a904971a.
M.-Y. Chae and A.W. Czarnik, J. Am. Chem. Soc., 114, 9704 (1992); https://doi.org/10.1021/ja00050a085.
G. Zhang, D. Zhang, S. Yin, X. Yang, Z. Shuai and D. Zhu, Chem. Commun., 2161 (2005); https://doi.org/10.1039/b417952h.
B. Liu and H. Tian, Chem. Commun., 3156 (2005); https://doi.org/10.1039/b501913c.
K.C. Song, J.S. Kim, S.M. Park, K.-C. Chung, S. Ahn and S.-K. Chang, Org. Lett., 8, 3413 (2006); https://doi.org/10.1021/ol060788b.
X. Zhang, Y. Xiao and X. Qian, Angew. Chem. Int. Ed., 47, 8025 (2008); https://doi.org/10.1002/anie.200803246.
M. Kumar, R. Kumar and V. Bhalla, Chem. Commun., 7384 (2009); https://doi.org/10.1039/b914821c.
V. Bhalla, Roopa, M. Kumar, P.R. Sharma and T. Kaur, Inorg. Chem., 51, 2150 (2012); https://doi.org/10.1021/ic201990q.
M. Kumar, N. Kumar, V. Bhalla, P.R. Sharma and Y. Qurishi, Chem. Commun., 48, 4719 (2012); https://doi.org/10.1039/c2cc30932g.
, V. Bhalla, M. Roopa and Kumar, Org. Lett., 14, 2802 (2012); https://doi.org/10.1021/ol301030z.