Synthesis and properties of three novel rhodamine-based fluorescent sensors for Hg2+

Miao-Miao Hong Ai-Feng Liu Ying Xu Dong-Mei Xu

引用本文: Miao-Miao Hong,  Ai-Feng Liu,  Ying Xu,  Dong-Mei Xu. Synthesis and properties of three novel rhodamine-based fluorescent sensors for Hg2+[J]. Chinese Chemical Letters, 2016, 27(6): 989-992. doi: 10.1016/j.cclet.2016.03.027 shu
Citation:  Miao-Miao Hong,  Ai-Feng Liu,  Ying Xu,  Dong-Mei Xu. Synthesis and properties of three novel rhodamine-based fluorescent sensors for Hg2+[J]. Chinese Chemical Letters, 2016, 27(6): 989-992. doi: 10.1016/j.cclet.2016.03.027 shu

Synthesis and properties of three novel rhodamine-based fluorescent sensors for Hg2+

  • 基金项目:

    This work was supported by the National Natural Science Foundation of China (No. 21074085), the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Graduate Student Innovation Training Project of Jiangsu Province (No. KYLX_1241), and the State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials.

摘要: Three novel rhodamine-based Hg2+ fluorescent sensors were designed and synthesized. The sensors could work in semi-aqueous solutions with nearly neutral pH and showed high selectivity and sensitivity to Hg2+ with remarkable fluorescence enhancement. For these three sensors, the linear working range broadened (0-80, 0-100 and 0-140 mmol/L, respectively) and the sensitivity increased (7.7, 15.5 and 17.6 folds of the fluorescence enhancement and 512, 66.2 and 37.6 ppb of the detection limit) with the rising of the thiourea-unit numbers. Furthermore the sensors exhibited excellent interference immunity tomultiple environmentally and biologically relevant metal ions. Pond and tap water assay showed good practicability of the sensors. The number of the bound Hg2+ equaling to that of the thiourea units and the irreversible recognition process implied a new interaction way between Hg2+ and the sensor.

English

    1. [1] Y.L. Liu, X. Lv, Y. Zhao, et al., A naphthalimide-rhodamine ratiometric fluorescent probe for Hg2+ based on fluorescence resonance energy transfer, Dyes Pigments 92 (2012) 909-915.

    2. [2] S.Y. Yu, S.P.Wu, A highly selective turn-on fluorescence chemosensor for Hg(II) and its application in living cell imaging, Sens. Actuators B: Chem. 201 (2014) 25-30.

    3. [3] D.T. Quang, J.S. Kim, Fluoro-and chromogenic chemodosimeters for heavy metal ion detection in solution and biospecimens, Chem. Rev. 110 (2010) 6280-6301.

    4. [4] X.H. Qian, Z.C. Xu, Fluorescence imaging of metal ions implicated in diseases, Chem. Soc. Rev. 44 (2015) 4487-4493.

    5. [5] Z.Y. Zhang, S.Z. Lu, C.M. Sha, et al., A single thiourea-appended 1,8-naphthalimide chemosensor for three heavy metal ions: Fe3+, Pb2+, and Hg2+, Sens. Actuators B: Chem. 208 (2015) 258-266.

    6. [6] S. Huang, R. Han, Q. Zhuang, et al., New photostable naphthalimide-based fluorescent probe for mitochondrial imaging and tracking, Biosens. Bioelectron. 71 (2015) 313-321.

    7. [7] Y. Ding, W.P. Zhu, Y.F. Xu, et al., A small molecular fluorescent sensor functionalized silica microsphere for detection and removal of mercury, cadmium, and lead ions in aqueous solutions, Sens. Actuators B: Chem. 220 (2015) 762-771.

    8. [8] Y. Mao, M.M. Hong, A.F. Liu, D.M. Xu, Highly selective and sensitive detection of Hg(II) from HgCl2 by a simple rhodamine-based fluorescent sensor, J. Fluoresc. 25 (2015) 755-761.

    9. [9] N. Wanichacheva, P. Praikaew, T. Suwanich, et al., "Naked-eye" colorimetric and "turn-on" fluorometric chemosensors for reversible Hg2+ detection, Spectrochim. Acta, Part A 118 (2014) 908-914.

    10. [10] C.J. Li, K.Q. Xiang, Y.C. Liu, et al., A novel colorimetric chemosensor for Cu2+ with high selectivity and sensitivity based on Rhodamine B, Res. Chem. Intermed. 41 (2015) 10169-10180.

    11. [11] M. Kumar, N. Kumar, V. Bhalla, Rhodamine appended thiacalix[4]arene of 1,3-alternate conformation for nanomolar detection of Hg2+ ions, Sens. Actuators B 161 (2012) 311-316.

    12. [12] F.Y. Yan, M. Wang, D.L. Cao, et al., New fluorescent and colorimetric chemosensors based on the rhodamine detection of Hg2+ and Al3+ and application of imaging in living cells, Dyes Pigments 98 (2013) 42-50.

    13. [13] T.K. Khan, M. Ravikanth, 3-(Pyridine-4-thione)BODIPY as a chemodosimeter for detection of Hg(II) ions, Dyes Pigments 95 (2012) 89-95.

    14. [14] H.D. Xiao, J.H. Li, K.T. Wu, et al., A turn-on BODIPY-based fluorescent probe for Hg(II) and its biological applications, Sens. Actuators B: Chem. 213 (2015) 343-350.

    15. [15] E. Karakus, M. Ucuncu, M. Emrullahoğlu, A rhodamine/BODIPY-based fluorescent probe for the differential detection of Hg(II) and Au(III), Chem. Commun. 50 (2014) 1119-1121.

    16. [16] S. Yang, W. Yang, Q. Guo, et al., A highly selective and ratiometric fluorescence probe for the detection of Hg2+ and pH change based on coumarin in aqueous solution, Tetrahedron 70 (2014) 8914-8918.

    17. [17] B. Gao, W.T. Gong, Q.L. Zhang, et al., A selective "turn-on" fluorescent sensor for Hg2+ based on "reactive" 7-hydroxycoumarin compound, Sens. Actuators B: Chem. 162 (2012) 391-395.

    18. [18] M.H. Lee, H.J. Kim, S. Yoon, et al., Metal ion induced FRET off-on in tren/dansylappended rhodamine, Org. Lett. 10 (2008) 213-216.

    19. [19] J. Isaad, A.E. Achari, Azathia crown ether possessing a dansyl fluorophore moiety functionalized silica nanoparticles as hybrid material for mercury detection in aqueous medium, Tetrahedron 69 (2013) 4866-4874.

    20. [20] J.H. Hu, J.B. Li, J. Qi, J.J. Chen, Highly selective and effective mercury(II) fluorescent sensors, New J. Chem. 39 (2015) 843-848.

    21. [21] Q.P. Hu, Y.L. Liu, Z.Q. Li, et al., A new rhodamine-based dual chemosensor for Al3+ and Cu2+, Tetrahedron Lett. 55 (2014) 4912-4916.

    22. [22] X.Q. Chen, T. Pradhan, F. Wang, et al., Fluorescent chemosensors based on spiroring-opening of Xanthenes and related derivatives, Chem. Rev. 112 (2012) 1910-1956.

    23. [23] Z. Liu, W. He, M.S. Pei, G.Y. Zhang, A fluorescent sensor with a detection level of pM for Cd2+ and nM for Cu2+ based on different mechanisms, Chem. Commun. 51 (2015) 14227-14230.

    24. [24] J.H. Huang, Y.F. Xu, X.H. Qian, A rhodamine-based Hg2+ sensor with high selectivity and sensitivity in aqueous solution: a NS2-containing receptor, J. Org. Chem. 74 (2009) 2167-2170.

    25. [25] H.L. Chen, Z.F. Guo, Z.L. Lu, Controlling ion-sensing specificity of N-amidothioureas: from anion-selective sensors to highly Zn2+ selective sensors by tuning electronic effects, Org. Lett. 14 (2012) 5070-5073.

    26. [26] B. Bag, A. Pal, Rhodamine-based probes for metal ion-induced chromo-fluorogenic dual signaling and their selectivity towards Hg(II) ion, Org. Biomol. Chem. 9 (2011) 4467-4480.

    27. [27] A.F. Liu, L. Yang, Z.Y. Zhang, et al., A novel rhodamine-based colorimetric and fluorescent sensor for the dual-channel detection of Cu2+ and Fe3+ in aqueous solutions, Dyes Pigments 99 (2013) 472-479.

    28. [28] W. Shi, H.M. Ma, Rhodamine B thiolactone: a simple chemosensor for Hg2+ in aqueous media, Chem. Commun. 16 (2008) 1856-1858.

    29. [29] J.S. Wu, I.C. Hwang, K.S. Kim, et al., Rhodamine-based Hg2+-selective chemodosimeter in aqueous solution: fluorescent off-on, Org. Lett. 9 (2007) 907-910.

    30. [30] S. Angupillai, J.Y. Hwang, J.Y. Lee, et al., Efficient rhodamine-thiosemicarbazidebased colorimetric/fluorescent ‘turn-on' chemodosimeters for the detection of Hg2+ in aqueous samples, Sens. Actuators B: Chem. 214 (2015) 101-110.

    31. [31] F.H. Wang, C.W. Cheng, L.C. Duan, et al., Highly selective fluorescent sensor for Hg2+ ion based on a novel rhodamine B derivative, Sens. Actuators B: Chem. 206 (2015) 678-683.

    32. [32] G.K. Wang, Q.L. Mi, L.Y. Zhao, et al., A pyrene derivative for Hg2+-selective fluorescent sensing and its application in in vivo imaging, Chem. Asian J. 9 (2014) 744-748.

  • 加载中
计量
  • PDF下载量:  1
  • 文章访问数:  1412
  • HTML全文浏览量:  18
文章相关
  • 收稿日期:  2016-01-30
  • 修回日期:  2016-03-11
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章