Abstract
Fluorogenic methods in conjunction with suitable probes have emerged as preferable modalities for the monitoring and measurement of trace metal ions. The number of new Zn2+-responsive fluorescent chemosensors has increased substantially in recent years, as a consequence of biologically and environmental importance of zinc ions, comprising organic fluorophore derivatives, biological functional materials and so on. In this review, we highlight recent advances made in the development of Zn2+ fluorescent sensors. This paper focuses on reviewing sensor molecules based on organic fluorophore derivatives, involving quinoline, BODIPY, coumarin, and so forth. On the basis of current research results, novel fluorescent chemosensors for zinc ions derived from organic fluorophores will be synthesized to increase the sensitivity, water solubility, and bio-compatibility of the sensor for in vivo analysis.
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X.M. Meng, S.X. Wang, Y.M. Li, M.Z. Zhu, Q.X. Guo, Chem. Commun. 48, 4196 (2012)
S.L. Sensi, L.M. Canzoniero, S.P. Yu, H.S. Ying, J.Y. Koh, G.A. Kershner, D.W. Choi, J. Neurosci. 17, 9554 (1997)
B.L. Vallee, K.H. Falchuk, Physiol. Rev. 73, 79 (1993)
Z.C. Xu, J.Y. Yoon, D.R. Spring, Chem. Soc. Rev. 39, 1996 (2010)
C. Rensing, R.M. Maier, Ecotoxicol. Environ. Saf. 56, 140 (2003)
A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, T.E. Rice, Chem. Rev. 97, 1515 (1997)
X. Chen, X. Tian, I. Shin, Yoon. J. Chem. Soc. Rev. 40, 4783 (2011)
H. Szmacinski, I. Gryczynski, J.R. Lakowicz, Photochem. Photobiol. 58, 341 (1993)
M. Formica, V. Fusi, L. Giorgi, M. Micheloni, Coord. Chem. Rev. 256, 170 (2012)
J. Wu, W. Liu, J. Ge, H. Zhang, P. Wang, Chem. Soc. Rev. 40, 3483 (2011)
P. Jiang, J. Guo, Coord. Chem. Rev. 248, 205 (2004)
P. Carol, S. Sreejith, A. Ajayaghosh, Chem. Asian J. 2, 338 (2007)
E.L. Que, D.W. Domaille, C.J. Chang, Chem. Rev. 108, 1517 (2008)
L. Xue, H.H. Wang, X.J. Wang, H. Jiang, Inorg. Chem. 47, 4310 (2008)
J.L. Wang, W.Y. Lin, W.L. Li, Chem. Eur. J. 18, 13629 (2012)
C.J. Frederickson, E.J. Kasarskis, D. Ringo, R.E. Frederickson, J. Neurosci. Methods 20, 91 (1987)
E.M. Nolan, J. Jaworski, K.I. Okamoto, Y. Hayashi, M. Sheng, S.J. Lippard, J. Am. Chem. Soc. 127, 16812 (2005)
X. Zhou, Y. Lu, J.F. Zhu, W.H. Chan, A.W.M. Lee, P.S. Chan, R.N.S. Wong, N.K. Mak, Tetrahedron 67, 3412 (2011)
G. Xie, Y. Shi, F. Hou, H. Liu, L. Huang, P. Xi, F. Chen, Z. Zeng, Eur. J. Inorg. Chem. 2, 327 (2012)
C. Zhang, Y. Zhang, Y. Chen, Z. Xie, Z. Liu, X. Dong, W. He, C. Shen, Z. Guo, Inorg. Chem. Commun. 14, 304 (2011)
Y. Zhang, X. Guo, W. Si, L. Jia, X. Qian, Org. Lett. 10, 473 (2008)
Q.H. You, P.S. Chan, W.H. Chan, S.C.K. Hau, A.W.M. Lee, N.K. Mak, T.C.W. Mak, R.N.S. Wong, RSC Adv. 2, 11078 (2012)
P.X. Li, X.Y. Zhou, L.Z. Yang, R.Y. Huang, X.L. Tang, W. Dou, Q.Q. Zhao, W.S. Liu, Dalton Trans. 43, 706 (2014)
Y. Zhang, X.F. Guo, L.H. Jia, S.C. Xu, Z.H. Xu, L.B. Zheng, X.H. Qian, Dalton Trans. 41, 11776 (2012)
X.Y. Chen, J. Shi, Y.M. Li, F.L. Wang, X. Wu, Q.X. Guo, L. Liu, Org. Lett. 19, 4426 (2009)
J. Luo, W.S. Li, P. Xu, L.Y. Zhang, Z.N. Chen, Inorg. Chem. 51, 9508 (2012)
X.Y. Chen, J. Shi, Y.M. Li, F.L. Wang, X. Wu, Q.X. Guo, L. Liu, Org. Lett. 19, 4426 (2009)
E.H. Hao, T. Meng, M. Zhang, W.D. Pang, Y.Y. Zhou, L.J. Jiao, J. Phys. Chem. A 115, 8234 (2011)
X.M. Meng, S.X. Wang, Y.M. Li, M.Z. Zhu, Q.X. Guo, Chem. Commun. 48, 4196 (2012)
N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 41, 1130 (2012)
Z.L. Fang, Flow injection separation and preconcentration (VCH Publisher, Weinheim, 1993)
M. Shamsipur, M.M. Zahedi, G.D. Filippo, V. Lippolis, Talanta 85, 687 (2011)
L. Xue, G.P. Li, D.J. Zhu, Q. Liu, H. Jiang, Inorg. Chem. 51, 10842 (2012)
H. He, D.K.P. Ng, Chem. Asian J. 8, 1441 (2013)
H. Zhu, J.L. Fan, S.L. Zhang, J.F. Cao, K.D. Song, D. Ge, H.J. Dong, J.Y. Wang, X.J. Peng, Biomater. Sci. 2, 89 (2014)
S.L. Zhu, J.T. Zhang, J. Janjanam, G. Vegesna, F.T. Luo, A. Tiwari, H.Y. Liu, J. Mater. Chem. B 1, 1722 (2013)
Z.Q. Guo, W.H. Zhu, M.M. Zhu, X.M. Wu, H. Tian, Chem. Eur. J. 16, 14424 (2010)
E. Sasaki, H. Kojima, H. Nishimatsu, Y. Urano, K. Kikuchi, Y. Hirata, T. Nagano, J. Am. Chem. Soc. 127, 3684 (2005)
B. Tang, F. Yu, P. Li, L. Tong, X. Duan, T. Xie, X. Wang, J. Am. Chem. Soc. 131, 3016 (2009)
L. Yuan, W.Y. Lin, Y.T. Yang, H. Chen, J. Am. Chem. Soc. 134, 1200 (2012)
Q. Zhao, C.H. Huang, F.Y. Li, Chem. Soc. Rev. 40, 2508 (2011)
P. Li, X. Duan, Z.Z. Chen, Y. Liu, T. Xie, L. Fang, X.R. Li, M. Lin, B. Tang, Chem. Commun. 47, 7755 (2011)
K.T. Arun, D. Ramaiah, J. Phys. Chem. A 109, 5571 (2005)
J.Y. Shao, H.Y. Sun, H.M. Guo, S.M. Ji, J.Z. Zhao, W.T. Wu, X.L. Yuan, C.L. Zhang, T.D. James, Chem. Sci. 3, 1049 (2012)
K. Kiyose, H. Kojima, Y. Urano, T. Nagano, J. Am. Chem. Soc. 128, 6548 (2006)
C.H. Hung, G.F. Chang, A. Kumar, G.F. Lin, L.Y. Luo, W.M. Ching, E.W.G. Diau, Chem. Commun. 8, 978 (2008)
S. Atilgan, T. Ozdemir, E.U. Akkaya, Org. Lett. 10, 4065 (2008)
X.Y. Lu, W.H. Zhu, Y.S. Xie, X. Li, Y. Gao, F.Y. Li, H. Tian, Chem. Eur. J. 16, 8355 (2010)
X.W. Cao, W.Y. Lin, W. Wan, Chem. Commun. 48, 6247 (2012)
L.N. Wang, W.W. Qin, X.L. Tang, W. Dou, W.S. Liu, J. Phys. Chem. A 115, 1609 (2011)
S. Dutta, P. Biswas, U. Flörke, K. Nag, Inorg. Chem. 49, 7382 (2010)
J. Wang, C. He, P.Y. Wu, J. Wang, C.Y. Duan, J. Am. Chem. Soc. 133, 12402 (2011)
S. Panda, P.B. Pati, S.S. Zade, Chem. Commun. 47, 4174 (2011)
J. Wu, W. Liu, X. Zhuang, F. Wang, P. Wang, S. Tao, X. Zhang, S. Wu, S.T. Lee, Org. Lett. 9, 33 (2007)
J.S. Wu, J.H. Zhou, P.F. Wang, X.H. Zhang, S.K. Wu, Org. Lett. 7, 2133 (2005)
M.A. Hortalá, L. Fabbrizzi, N. Marcotte, F. Stomeo, A. Taglietti, J. Am. Chem. Soc. 125, 20 (2003)
C. Zhao, P. Feng, J. Cao, Y. Zhang, X. Wang, Y. Yang, Y. Zhang, J. Zhang, Org. Biomol. Chem. 10, 267 (2012)
C. Zhao, Y. Zhou, Q. Lin, L. Zhu, P. Feng, Y. Zhang, J. Cao, J. Phys. Chem. B 115, 642 (2011)
C. Zhao, P. Feng, J. Cao, X. Wang, Y. Yang, Y. Zhang, J. Zhang, Y. Zhang, Org. Biomol. Chem. 10, 3104 (2012)
J. Cao, C. Zhao, P. Feng, Y. Zhang, W. Zhu, RSC Adv. 2, 418 (2012)
H.M. Guo, Y.Y. Jing, X.L. Yuan, S.M. Ji, J.Z. Zhao, X.H. Li, Y.Y. Kan, Org. Biomol. Chem. 9, 3844 (2011)
J. Cao, C.C. Zhao, X.Z. Wang, Y.F. Zhang, W.H. Zhu, Chem. Commun. 48, 9897 (2012)
L. Yuan, W.Y. Lin, K.B. Zheng, L.W. He, W.M. Huang, Chem. Soc. Rev. 42, 622 (2013)
J.A. Richard, M. Massonneau, P.Y. Renard, A. Romieu, Org. Lett. 10, 4175 (2008)
Y.J. Jang, B.S. Moon, M.S. Park, B.G. Kang, J.Y. Kwon, J.S.J. Hong, Y.J. Yoon, K.D. Lee, J. Yoon, Tetrahedron Lett. 47, 2707 (2006)
D. Ray, A. Nag, A. Jana, D. Goswami, P.K. Bharadwaj, Inorg. Chim. Acta 363, 2824 (2010)
M. Formica, V. Fusi, L. Giorgi, M. Micheloni, Coord. Chem. Rev. 256, 170 (2012)
Z. Xu, K. Baek, H.N. Kim, J. Cui, X. Qian, D.R. Spring, I. Shin, J. Yoon, J. Am. Chem. Soc. 132, 601 (2010)
Z.C. Xu, X. Liu, J. Pan, D.R. Spring, Chem. Commun. 48, 4764 (2012)
L. Xue, Q. Liu, H. Jiang, Org. Lett. 11, 3454 (2009)
S. Sumiya, Y. Shiraishi, T. Hirai, J. Phys. Chem. A 117, 1474 (2013)
C.E. Wheelock, J. Am. Chem. Soc. 81, 1348 (1959)
M.E. Huston, K.W. Haider, A.W. Czarnik, J. Am. Chem. Soc. 110, 4460 (1988)
Y. Ding, X. Li, T. Li, W. Zhu, Y. Xie, J. Org. Chem. 78, 5328 (2013)
Z. Su, K.Y. Chen, Y. Guo, H.P. Qi, X.F. Yang, M.L. Zhao, J. Fluoresc. 20, 851 (2010)
V. Kumar, A. Kumar, U. Diwan, K.K. Upadhyay, Dalton Trans. 42, 13078 (2013)
N.C. Lim, J.V. Schuster, M.C. Porto, M.A. Tanudra, L. Yao, H.C. Freake, C. Brückner, Inorg. Chem. 44, 2018 (2005)
D. Ray, A. Nag, A. Jana, D. Goswami, P.K. Bharadwaj, Inorg. Chem. Acta. 363, 2824 (2010)
P. Molina, A. Tárraga, F. Otón, Org. Biomol. Chem. 10, 1711 (2012)
I.J. Rhile, T.F. Markle, H. Nagao, A.G. DiPasquale, O.P. Lam, M.A. Lockwood, K. Rotter, J.M. Mayer, J. Am. Chem. Rev. 128, 6075 (2006)
T.F. Markle, I.J. Rhile, A.G. DiPasquale, J.M. Mayer, Proc. Natl. Acad. Sci. USA. 105, 8185 (2008)
A.O. Eseola, W. Li, R. Gao, M. Zhang, X. Hao, T. Liang, N.O. Obi-Egbedi, W.-H. Sun, Inorg. Chem. 48, 9133 (2009)
J.L. Wang, W.Y. Lin, W.L. Li, Chem. Eur. J. 18, 13629 (2012)
W. Lin, L. Long, L. Yuan, Z. Cao, B. Chen, W. Tan, Org. Lett. 10, 5577 (2008)
L. Xue, H.H. Wang, X.J. Wang, H. Jiang, Inorg. Chem. 47, 4310 (2008)
P. Carol, S. Sreejith, A. Ajayaghosh, Chem. Asian J. 2, 338 (2007)
S. Aoki, K. Sakurama, R. Ohshima, N. Matsuo, Y. Yamada, R. Takasawa, S. Tanuma, K. Takeda, E. Kimura, Inorg. Chem. 47, 2747 (2008)
A. El Majzoub, C. Cadiou, I. Déchamps-Olivier, F. Chuburu, M. Aplincourt, Eur. J. Inorg. Chem. 32, 5087 (2007)
A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. Mc Coy, J.T. Rademacher, T.E. Rice, Chem. Rev. 97, 1515 (1997)
N.C. Lim, H.C. Freake, C. Bruckner, Chem. Eur. J. 11, 38 (2005)
A. El Majzoub, C. Cadiou, I. Déchamps-Olivier, F. Chuburu, M. Aplincourt, B. Tinant, Inorg. Chim. Acta 362, 1169 (2009)
E. Tamanini, K. Flavin, M. Motevalli, S. Piperno, L.A. Gheber, M.H. Todd, M. Watkinson, Inorg. Chem. 49, 3789 (2010)
A. El Majzoub, C. Cadiou, I. Déchamps-Olivier, B. Tinant, F. Chuburu, Inorg. Chem. 50, 4029 (2011)
J. Wu, W. Liu, J. Ge, H. Zhang, P. Wang, Chem. Soc. Rev. 40, 3483 (2011)
M.M. Henary, Y. Wu, C.J. Fahrni, Chem. Eur. J. 10, 3015 (2004)
S. Santra, G. Krishnamoorthy, S.K. Dogra, J. Phys. Chem. A 104, 476 (2000)
L.J. Tang, M.J. Cai, P. Zhou, J. Zhao, K.L. Zhong, S.H. Hou, Y.J. Bian, RSC Adv. 3, 16802 (2013)
T.E. Mallouk, D.J. Harrison, Interfacial design and chemical sensing, ed. by A.W. Czarnik (American Chemical Society, Washington, DC, 1994), p. 314
R. Martínez-Máñez, F. Sancenón, Chem. Rev. 103, 4419 (2003)
M.M. Balamurali, S.K. Dogra, Chem. Phys. 305, 95 (2004)
M.J. Kim, K. Kaur, N. Singh, D.O. Jang, Tetrahedron 68, 5429 (2012)
Z. Xu, N.J. Singh, J. Lim, J. Pan, H.N. Kim, S. Park, K.S. Kim, J. Yoon, J. Am. Chem. Soc. 131, 15528 (2009)
Y. Yanga, X. Goub, Blechaa, H. Cao, Tetrahedron Lett. 51, 3422 (2010)
F.M. Winnik, Chem. Rev. 93, 587 (1993)
C. Yao, H.-B. Kraatz, R.P. Steer, Photochem. Photobiol. Sci. 4, 191 (2005)
J.B. Birks, Rep. Prog. Phys. 38, 903 (1975)
A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, T.E. Rice, Chem. Rev. 97, 1515 (1997)
J. Cho, T. Pradhan, J.S. Kim, S. Kim, Org. Lett. 15, 4058 (2013)
M. Juríček, P.H.J. Kouwer, A.E. Rowan, Chem. Commun. 47, 8740 (2011)
J. Cho, T. Pradhan, J.S. Kim, S. Kim, Org. Lett. 15, 4058 (2013)
V.D. Bock, H. Hiemstra, J.H. van Maarseveen, Eur. J. Org. Chem. 1, 51 (2006)
X.L. Ni, X. Zeng, C. Redshaw, T. Yamato, J. Org. Chem. 76, 5696 (2011)
S.K. Kim, D.H. Lee, J.I. Hong, J. Yoon, Acc. Chem. Res. 42, 23 (2009)
S.A. Ingale, F. Seela, J. Org. Chem. 77, 9352 (2012)
F.M. Winnik, Chem. Rev. 93, 587 (1993)
E. Manandhar, J.H. Broome, J.L. Myrick, W. Lagrone, P.J. Cragg, K.J. Wallace, Chem. Commun. 47, 8796 (2011)
X.Q. Chen, T. Pradhan, F. Wang, J.S. Kim, J. Yoon, Chem. Rev. 112, 1910 (2012)
G. Sivaraman, T. Anand, D. Chellappa, Analyst 137, 5881 (2012)
G. Chen, F.L. Song, X.Q. Xiong, X.J. Peng, Ing. Eng. Chem. Res. 52, 11228 (2013)
K. Sreenath, R.J. Clark, L. Zhu, J. Org. Chem. 77, 8268 (2012)
V. Luxami, Renukamal, K. Paul, S. Kumar, RSC. Adv. 3, 9189 (2013)
K. Tanaka, T. Kumagai, H. Aoki, M. Deguchi, S. Iwata, J. Org. Chem. 66, 7328 (2001)
Y. Shiraishi, Y. Matsunaga, T. Hirai, J. Phys. Chem. A 117, 3387 (2013)
J.E. Kwon, S. Lee, Y. You, K.H. Baek, K. Ohkubo, J. Cho, S. Fukuzumi, I. Shin, S.Y. Park, W. Nam, Inorg. Chem. 51, 8760 (2012)
T.B. Wei, P. Zhang, B.B. Shi, P. Chen, Q. Lin, J. Liu, Y.M. Zhang, Dyes Pigments 97, 297 (2013)
J.M. An, M.H. Yan, Z.Y. Yang, T.R. Li, Q.X. Zhou, Dyes Pigments 99, 1 (2013)
M. Hosseini, M.R. Ganjali, B. Veismohammadi, S. Riahi, P. Norouzi, M. Salavati-Niasari, S.D. Abkenar, Anal. Lett. 42, 1029 (2009)
M.R. Ganjali, A. Ghesmi, M. Hosseini, M.R. Pourjavid, M. Rezapour, M. Shamsipur, M.S. Niasari, Sens. Actuators B 105, 334 (2005)
M. Hosseini, H.B. Sadeghi, M. Rahimi, M.S. Niasari, S.D. Abkenar, K. Alizadeh, M.R. Ganjali, Electroanalysis 21, 859 (2009)
M. Hosseini, Z. Vaezi, M.R. Ganjali, F. Faridbod, S.D. Abkenar, K. Alizadeh, M.S. Niasari, Spectrochim Acta Part A 75, 978 (2010)
M. Hosseini, A. Ghafarloo, M.R. Ganjali, F. Faridbod, P. Norouzi, M.S. Niasari, Sens. Actuators B 198, 411 (2014)
J.S. Wu, W.M. Liu, X.Q. Zhuang, F. Wang, P.F. Wang, S.L. Tao, X.H. Zhang, S.K. Wu, S.T. Lee, Org. Lett. 9, 33 (2007)
M. Royzen, A. Durandin, V.G. Young, N.E. Geacintov, J.W. Canary, J. Am. Chem. Soc. 128, 3854 (2006)
M. Shamsipur, T. Poursaberi, M. Hassanisadi, M. Rezapour, F. Nourmohammadian, K. Alizadeh, Sens. Actuators B 161, 1080 (2012)
A.R. Rezvani, H. Saravani, H. Hadadzadeh, J. Iran. Chem. Soc. 7, 825 (2010)
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The work described in this manuscript was supported by the National Natural Science Foundation of China (Nos. 21174103, 21374078 and 31200719).
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Shi, D., Zhou, X., Zheng, T. et al. Recognition and fluorescent sensing of zinc ions using organic fluorophores-based sensor molecules. J IRAN CHEM SOC 12, 293–308 (2015). https://doi.org/10.1007/s13738-014-0484-9
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DOI: https://doi.org/10.1007/s13738-014-0484-9