A squaraine based fl uorescent probe for mercury ion <i>via</i> coordination induced deaggregation signaling

Citation: Shuang-Yong Lin, Hui-Jun Zhu, Wen-Jian Xu, Gui-Mei Wang, Nan-Yan Fu. A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling[J]. Chinese Chemical Letters, 2014, 25(9): 1291-1295. doi: 10.1016/j.cclet.2014.04.027 shu

A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling

通讯作者: Nan-Yan Fu,

基金项目:
This work was financially supported by the National Science Foundation for Fostering Talents in Basic Research of the National Natural Science Foundation of China (No. J1103303) (No. J1103303)

the National Natural Science Foundation of China (No. 20702005) (No. 20702005)

Technology, China (No. 2013Y0062) (No. 2013Y0062)

Funding (Type A) from Fujian Education Department, PR China (Nos. JA12038 (Type A)

Technology Development Fund of Fuzhou University, China (No. 600902). (No. 600902)

摘要: Due to the high affinity between dithiocarbamate (DTC) and Hg²⁺, a fluorescent probe based on squaraine chromophore with DTC side arm for Hg²⁺ via coordination induced deaggregation signaling has been designed and synthesized. Squaraine has a high tendency to aggregate in aqueous solution, and such self-aggregation usually results in a dramatic absorption spectral broadening with fluorescence emission quenching. The combination of the DTC side arm of the probe with Hg²⁺ induces steric hindrance, leading to the deaggregation of the dye complex, companying with a fluorescence emission restoration. In EtOH-H₂O (20:80, v/v) solution, this "turn on" fluorescent probe has high selectivity and sensitivity toward Hg²⁺ over other metal ions, and the limit of detection for Hg²⁺ was estimated as 2.19×10^-8mol/L by 3σ/k.

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English

A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling

1.
Key Laboratory of Analysis and Detection for Food Safety, Ministry of Education & Fujian Provincial Key Laboratory of Analysis and Detection Technology for Food Safety, College of Chemistry and Chemical Engineering, and Department of Chemistry, Fuzhou University, Fuzhou 350108, China

Corresponding author: Nan-Yan Fu,

Received Date: 03 January 2014
Fund Project:

Abstract: Due to the high affinity between dithiocarbamate (DTC) and Hg²⁺, a fluorescent probe based on squaraine chromophore with DTC side arm for Hg²⁺ via coordination induced deaggregation signaling has been designed and synthesized. Squaraine has a high tendency to aggregate in aqueous solution, and such self-aggregation usually results in a dramatic absorption spectral broadening with fluorescence emission quenching. The combination of the DTC side arm of the probe with Hg²⁺ induces steric hindrance, leading to the deaggregation of the dye complex, companying with a fluorescence emission restoration. In EtOH-H₂O (20:80, v/v) solution, this "turn on" fluorescent probe has high selectivity and sensitivity toward Hg²⁺ over other metal ions, and the limit of detection for Hg²⁺ was estimated as 2.19×10^-8mol/L by 3σ/k.

Key words:

1. [1] L. Magos, T.W. Clarkson, Overview of the clinical toxicity of mercury, Ann. Clin. Biochem. 43 (2006) 257-268.[1] L. Magos, T.W. Clarkson, Overview of the clinical toxicity of mercury, Ann. Clin. Biochem. 43 (2006) 257-268.
2. [2] F. Zahir, S.J. Rizwi, S.K. Haq, R.H. Khan, Low dose mercury toxicity and human health, Environ. Toxicol. Pharmacol. 20 (2005) 351-360.[2] F. Zahir, S.J. Rizwi, S.K. Haq, R.H. Khan, Low dose mercury toxicity and human health, Environ. Toxicol. Pharmacol. 20 (2005) 351-360.
3. [3] A. Taylor, S. Branch, D. Halls, M. Patriarca, M. White, Atomic spectrometry update. Clinical and biological materials, food and beverages, J. Anal. At. Spectrom. 17 (2002) 414-455.[3] A. Taylor, S. Branch, D. Halls, M. Patriarca, M. White, Atomic spectrometry update. Clinical and biological materials, food and beverages, J. Anal. At. Spectrom. 17 (2002) 414-455.
4. [4] D. Beauchemin, Inductively coupled plasma mass spectrometry, Anal. Chem. 80 (2008) 4455-4486.[4] D. Beauchemin, Inductively coupled plasma mass spectrometry, Anal. Chem. 80 (2008) 4455-4486.
5. [5] E.M. Nolan, S.J. Lippard, Tools and tactics for the optical detection of mercuric ion, Chem. Rev. 108 (2008) 3443-3480.[5] E.M. Nolan, S.J. Lippard, Tools and tactics for the optical detection of mercuric ion, Chem. Rev. 108 (2008) 3443-3480.
6. [6] P. Mahato, S. Saha, E. Suresh, et al., Ratiometric detection of Cr³⁺ and Hg²⁺ by a naphthalimide-rhodamine based fluorescent probe, Inorg. Chem. 51 (2012) 1769-1777.[6] P. Mahato, S. Saha, E. Suresh, et al., Ratiometric detection of Cr³⁺ and Hg²⁺ by a naphthalimide-rhodamine based fluorescent probe, Inorg. Chem. 51 (2012) 1769-1777.
7. [7] X. Ma, J. Wang, Q. Shan, et al., A "turn-on" fluorescent Hg²⁺ chemosensor based on Ferrier carbocyclization, Org. Lett. 14 (2012) 820-823.[7] X. Ma, J. Wang, Q. Shan, et al., A "turn-on" fluorescent Hg²⁺ chemosensor based on Ferrier carbocyclization, Org. Lett. 14 (2012) 820-823.
8. [8] Y.J. Gong, X.B. Zhang, C.C. Zhang, et al., Through bond energy transfer: a convenient and universal strategy toward efficient ratiometric fluorescent probe for bioimaging applications, Anal. Chem. 84 (2012) 10777-10784.[8] Y.J. Gong, X.B. Zhang, C.C. Zhang, et al., Through bond energy transfer: a convenient and universal strategy toward efficient ratiometric fluorescent probe for bioimaging applications, Anal. Chem. 84 (2012) 10777-10784.
9. [9] X.M. Meng, M.Z. Zhu, Q.X. Guo, A novel highly selective fluorescent chemosensor for Hg(II) in fully aqueous media, Chin. Chem. Lett. 18 (2007) 1209-1212.[9] X.M. Meng, M.Z. Zhu, Q.X. Guo, A novel highly selective fluorescent chemosensor for Hg(II) in fully aqueous media, Chin. Chem. Lett. 18 (2007) 1209-1212.
10. [10] X.M. Wang, H. Yan, X.L. Feng, Y. Chen, 1-Pyrenecarboxaldehyde thiosemicarbazone: a novel fluorescent molecular sensor towards mercury (II) ion, Chin. Chem. Lett. 21 (2010) 1124-1128.[10] X.M. Wang, H. Yan, X.L. Feng, Y. Chen, 1-Pyrenecarboxaldehyde thiosemicarbazone: a novel fluorescent molecular sensor towards mercury (II) ion, Chin. Chem. Lett. 21 (2010) 1124-1128.
11. [11] L. Hu, Z.Q. Yan, H.Y. Xu, Advances in synthesis and application of near-infrared absorbing squaraine dyes, RSC Adv. 3 (2013) 7667-7676.[11] L. Hu, Z.Q. Yan, H.Y. Xu, Advances in synthesis and application of near-infrared absorbing squaraine dyes, RSC Adv. 3 (2013) 7667-7676.
12. [12] C. Chen, R.Y. Wang, N.Y. Fu, Squaraine dyes for ion recognition, Prog. Chem. 23 (2011) 739-749.[12] C. Chen, R.Y. Wang, N.Y. Fu, Squaraine dyes for ion recognition, Prog. Chem. 23 (2011) 739-749.
13. [13] Z. Wang, R. Wang, N. Fu, Advances of squaraine dyes in organic solar cells, Chin. J. Org. Chem. 31 (2011) 415-425.[13] Z. Wang, R. Wang, N. Fu, Advances of squaraine dyes in organic solar cells, Chin. J. Org. Chem. 31 (2011) 415-425.
14. [14] Y.W. Huang, N.Y. Fu, Synthesis and properties of a novel squaraine dye modified by ferrocene, Chin. Chem. Lett. 22 (2011) 1301-1304.[14] Y.W. Huang, N.Y. Fu, Synthesis and properties of a novel squaraine dye modified by ferrocene, Chin. Chem. Lett. 22 (2011) 1301-1304.
15. [15] Q. Lin, Y. Huang, J. Fan, R. Wang, N. Fu, A squaraine and Hg²⁺-based colorimetric and "turn on" fluorescent probe for cysteine, Talanta 114 (2013) 66-72.[15] Q. Lin, Y. Huang, J. Fan, R. Wang, N. Fu, A squaraine and Hg²⁺-based colorimetric and "turn on" fluorescent probe for cysteine, Talanta 114 (2013) 66-72.
16. [16] J. Fan, C. Chen, Q. Lin, N. Fu, A fluorescent probe for the dual-channel detection of Hg²⁺/Ag⁺¹ and its Hg²⁺-based complex for detection of mercapto biomolecules with a tunable measuring range, Sens. Actuators B: Chem. 173 (2012) 874-881.[16] J. Fan, C. Chen, Q. Lin, N. Fu, A fluorescent probe for the dual-channel detection of Hg²⁺/Ag⁺¹ and its Hg²⁺-based complex for detection of mercapto biomolecules with a tunable measuring range, Sens. Actuators B: Chem. 173 (2012) 874-881.
17. [17] K.M. Shafeekh, M.K.A. Rahim, M.C. Basheer, C.H. Suresh, S. Das, Highly selective and sensitive colourimetric detection of Hg²⁺ ions by unsymmetrical squaraine dyes, Dyes Pigm. 96 (2013) 714-721.[17] K.M. Shafeekh, M.K.A. Rahim, M.C. Basheer, C.H. Suresh, S. Das, Highly selective and sensitive colourimetric detection of Hg²⁺ ions by unsymmetrical squaraine dyes, Dyes Pigm. 96 (2013) 714-721.
18. [18] L. Hu, Y. Zhang, L. Nie, C. Xie, Z. Yan, Colorimetric detection of trace Hg²⁺ with near-infrared absorbing squaraine functionalized by dibenzo-18-crown-6 and its mechanism, Spectrochim. Acta A 104 (2013) 87-91.[18] L. Hu, Y. Zhang, L. Nie, C. Xie, Z. Yan, Colorimetric detection of trace Hg²⁺ with near-infrared absorbing squaraine functionalized by dibenzo-18-crown-6 and its mechanism, Spectrochim. Acta A 104 (2013) 87-91.
19. [19] Y. Xu, Z. Li, A. Malkovskiy, S. Sun, Y. Pang, Aggregation control of squaraines and their use as near-infrared fluorescent sensors for protein, J. Phys. Chem. B 114 (2010) 8574-8580.[19] Y. Xu, Z. Li, A. Malkovskiy, S. Sun, Y. Pang, Aggregation control of squaraines and their use as near-infrared fluorescent sensors for protein, J. Phys. Chem. B 114 (2010) 8574-8580.
20. [20] Y. Huang, Q. Lin, J. Wu, N. Fu, Design and synthesis of a squaraine based nearinfrared fluorescent probe for the ratiometric detection of Zn²⁺ ions, Dyes Pigm. 99 (2013) 699-704.[20] Y. Huang, Q. Lin, J. Wu, N. Fu, Design and synthesis of a squaraine based nearinfrared fluorescent probe for the ratiometric detection of Zn²⁺ ions, Dyes Pigm. 99 (2013) 699-704.
21. [21] W.D. Wang, A. Fu, J.S. You, et al., Squaraine-based colorimetric and fluorescent sensors for Cu²⁺-specific detection and fluorescence imaging in living cells, Tetrahedron 66 (2010) 3695-3701.[21] W.D. Wang, A. Fu, J.S. You, et al., Squaraine-based colorimetric and fluorescent sensors for Cu²⁺-specific detection and fluorescence imaging in living cells, Tetrahedron 66 (2010) 3695-3701.
22. [22] J.V. Ros-Lis, R. Martínez-Máñez, F. Sancenón, et al., Squaraines as reporter units: insights into their photophysics, protonation, and metal-ion coordination behaviour, Chem. Eur. J. 14 (2008) 10101-10114.[22] J.V. Ros-Lis, R. Martínez-Máñez, F. Sancenón, et al., Squaraines as reporter units: insights into their photophysics, protonation, and metal-ion coordination behaviour, Chem. Eur. J. 14 (2008) 10101-10114.
23. [23] J.V. Ros-Lis, R. Martínez-Máñez, J. Soto, L.A. Villaescusa, K. Rurack, Squaraine "ships" in the Y zeolite "bottle": a chromogenic sensing material for the detection of volatile amines and thiols, J. Mater. Chem. 21 (2011) 5004-5010.[23] J.V. Ros-Lis, R. Martínez-Máñez, J. Soto, L.A. Villaescusa, K. Rurack, Squaraine "ships" in the Y zeolite "bottle": a chromogenic sensing material for the detection of volatile amines and thiols, J. Mater. Chem. 21 (2011) 5004-5010.
24. [24] S. Sreejith, K.P. Divya, A. Ajayaghosh, A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma, Angew. Chem. Int. Ed. 47 (2008) 7883-7887.[24] S. Sreejith, K.P. Divya, A. Ajayaghosh, A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma, Angew. Chem. Int. Ed. 47 (2008) 7883-7887.
25. [25] C.G. Sun, Q. Lin, N.Y. Fu, A novel squaraine dye with squaramide as a scaffold and the colorimetric detection of amine, Chin. Chem. Lett. 23 (2012) 217-220.[25] C.G. Sun, Q. Lin, N.Y. Fu, A novel squaraine dye with squaramide as a scaffold and the colorimetric detection of amine, Chin. Chem. Lett. 23 (2012) 217-220.
26. [26] A. Ajayaghosh, E. Arunkumar, J. Daub, A highly specific Ca²⁺-ion sensor: signaling by exciton interaction in a rigid-flexible-rigid bichromophoric "H" foldamer, Angew. Chem. Int. Ed. 41 (2002) 1766-1769.[26] A. Ajayaghosh, E. Arunkumar, J. Daub, A highly specific Ca²⁺-ion sensor: signaling by exciton interaction in a rigid-flexible-rigid bichromophoric "H" foldamer, Angew. Chem. Int. Ed. 41 (2002) 1766-1769.
27. [27] Y. Xu, M.J. Panzner, X. Li, W.J. Youngs, Y. Pang, Host-guest assembly of squaraine dye in cucurbit[8]uril: its implication in fluorescent probe for mercury ions, Chem. Commun. 46 (2010) 4073-4075.[27] Y. Xu, M.J. Panzner, X. Li, W.J. Youngs, Y. Pang, Host-guest assembly of squaraine dye in cucurbit[8]uril: its implication in fluorescent probe for mercury ions, Chem. Commun. 46 (2010) 4073-4075.
28. [28] Y. Xu, A. Malkovskiy, Q. Wang, Y. Pang, Molecular assembly of a squaraine dye with cationic surfactant and nucleotides: its impact on aggregation and fluorescence response, Org. Biomol. Chem. 9 (2011) 2878-2884.[28] Y. Xu, A. Malkovskiy, Q. Wang, Y. Pang, Molecular assembly of a squaraine dye with cationic surfactant and nucleotides: its impact on aggregation and fluorescence response, Org. Biomol. Chem. 9 (2011) 2878-2884.
29. [29] E. Arunkumar, A. Ajayaghosh, J. Daub, Selective calcium ion sensing with a bichromophoric squaraine foldamer, J. Am. Chem. Soc. 127 (2005) 3156-3164.[29] E. Arunkumar, A. Ajayaghosh, J. Daub, Selective calcium ion sensing with a bichromophoric squaraine foldamer, J. Am. Chem. Soc. 127 (2005) 3156-3164.
30. [30] J.V. Ros-Lis, R. Martínez-Máňez, K. Rurack, et al., Highly selective chromogenic signaling of Hg²⁺ in aqueous media at nanomolar levels employing a squarainebased reporter, Inorg. Chem. 43 (2004) 5183-5185.[30] J.V. Ros-Lis, R. Martínez-Máňez, K. Rurack, et al., Highly selective chromogenic signaling of Hg²⁺ in aqueous media at nanomolar levels employing a squarainebased reporter, Inorg. Chem. 43 (2004) 5183-5185.
31. [31] X.H. Li, B.W. Zhang, Y. Cao, Aggregation of bis(2,4,6-trihydroxyphenyl) squaraine in different solutions, Dyes Pigm. 45 (2000) 209-217.[31] X.H. Li, B.W. Zhang, Y. Cao, Aggregation of bis(2,4,6-trihydroxyphenyl) squaraine in different solutions, Dyes Pigm. 45 (2000) 209-217.
32. [32] C. Chen, R. Wang, L. Guo, et al., A squaraine-based colorimetric and "turn on" fluorescent sensor for selective detection of Hg²⁺ in an aqueous medium, Org. Lett. 13 (2011) 1162-1165.[32] C. Chen, R. Wang, L. Guo, et al., A squaraine-based colorimetric and "turn on" fluorescent sensor for selective detection of Hg²⁺ in an aqueous medium, Org. Lett. 13 (2011) 1162-1165.
33. [33] G.R. Clemo, W.H. Perkin, LXXIV.-Introduction of the chloroethyl group into phenols, alcohols, and amino-compounds, J. Chem. Soc. Trans. 121 (1922) 642-649.[33] G.R. Clemo, W.H. Perkin, LXXIV.-Introduction of the chloroethyl group into phenols, alcohols, and amino-compounds, J. Chem. Soc. Trans. 121 (1922) 642-649.
34. [34] M. Matsui, K. Nagasaka, S. Tokunaga, et al., 3-Aryl-4-hydroxycyclobut-3-ene-1,2-diones as sensitizers for TiO solar cell, Dyes Pigm. 58 (2003) 219-226.[34] M. Matsui, K. Nagasaka, S. Tokunaga, et al., 3-Aryl-4-hydroxycyclobut-3-ene-1,2-diones as sensitizers for TiO solar cell, Dyes Pigm. 58 (2003) 219-226.

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沈阳化工大学材料科学与工程学院沈阳 110142

A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling

通讯作者: Nan-Yan Fu,

English

A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling

Corresponding author: Nan-Yan Fu,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling

通讯作者: Nan-Yan Fu,

English

A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling

Corresponding author: Nan-Yan Fu,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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