Chinese Journal of Organic Chemistry >
Design, Synthesis and Application of Fluorescence Resonance Energy Transfer-Based Ratiometric Hydrazine Fluorescent Probe
Received date: 2018-11-28
Revised date: 2019-01-07
Online published: 2019-01-18
Supported by
Project supported by the National Natural Scinec Foundation of China (No. 51578067), the Natural Science Foundation of Hebei Provience (No. 2018201234), the Colleges and Universities Science Technology Research Project of Hebei Province (No. QN2017015) and the Science Technology Research and Development Guidance Programme Project of Baoding City (Nos. 16zg031, 18ZF315).
Hydrazine (N2H4) is a highly toxic biochemical reagent with the capability of mutagenic, teratogenic and carcinogenic. For accurately monitoring the concentration of N2H4 in the environment and life, two FRET (fluorescence resonance energy transfer)-based dual-emissive ratiometric fluorescent probes (FRET-1/2) were designed and synthesized. The structures of both probes were charactered by 1H NMR, 13C NMR and HRMS. The results prove that both probes exhibit good selectivity and sensitivity to N2H4 and can be used for detecting N2H4 in water samples.
Yang Ziqi , Liu Xingkun , Jiang Lu'nan , Wang Mei . Design, Synthesis and Application of Fluorescence Resonance Energy Transfer-Based Ratiometric Hydrazine Fluorescent Probe[J]. Chinese Journal of Organic Chemistry, 2019 , 39(5) : 1483 -1488 . DOI: 10.6023/cjoc201811034
[1] (a) Rosca, V.; Koper, Marc T. M. Electrochim. Acta 2008, 53, 5199.
(b) Khaled, K. F. Appl. Surf. Sci. 2006, 252, 4120.
(c) Kean, T.; Miller, J. H. M.; Skellern, G. G.; Snodin, D. Pharmeur. Sci. Notes 2006, 2006, 23.
[2] (a) Serov, A.; Kwak, C. Appl. Catal., B 2010, 98, 1.
(b) Garrod, S.; Bollard, M. E.; Nicholls A. W.; Connor, S. C.; Connelly, J.; Nicholson, J. K.; Holmes, E. Chem. Res. Toxicol. 2005, 18, 115.
[3] U.S. Environmental Protection Agency (EPA) Integrated Risk Information System (IRIS) on Hydrazine/Hydrazine Shlfate National Center for Environmental Assessment, Office of Research and Development, Washington, DC, 1999.
[4] Lei, B. F.; Wei, C.-J.; Tu, S.-C. J. Biol. Chem. 2000, 275, 2520.
[5] (a) Chen, X.; Wang, F.; Hyun, J. Y.; Wei, T.; Qiang, J.; Ren, X. Chem. Soc. Rev. 2016, 45, 2976.
(b) He, X.-P.; Hu, X.-L.; James, T. D.; Yoon, J.; Tian, H. Chem. Soc. Rev. 2017, 46, 6687.
(c) Wu, D.; Sedgwick, A. C.; Gunnlaugsson, T.; Akkaya, E. U.; Yoon, J.; James, T. D. Chem. Soc. Rev. 2017, 46, 7105.
(d) Sedgwick, A. C.; Wu, L.; Han, H-H.; Bull, S. D.; He, X-P.; James, T. D. Chem. Soc. Rev. 2018, 47, 8842.
[6] Cui, L.; Ji, C. F.; Peng, Z. X.; Zhong, L.; Zhou, C. H.; Yan, L. L.; Qu, S.; Zhang, S. P.; Huang, C.; Qian, X. H.; Xu, Y. F. Anal. Chem. 2014, 86, 4611.
[7] Cui, L.; Peng, Z. X.; Ji, C. F.; Huang, D. T.; Ma, J.; Zhang, S. P.; Qian, X. H.; Xu, Y. F. Chem. Commun. 2014, 50, 1485.
[8] Qian, Y.; Lin, J.; Han, L. J.; Lin, L.; Zhu, H. L. Biosens. Bioelectron. 2014, 58, 282.
[9] Zhang, J. J.; Ning, L. L.; Liu, J. T.; Wang, J. X.; Yu, B. F.; Liu, X. Y.; Yao, X. J.; Zhang, Z. P.; Zhang, H. X. Anal. Chem. 2015, 87, 9101.
[10] Firoj, A.; Anila, H. A.; Andaraj, T.; Mogare, D. G.; Samit, C.; Amitava, D. Chem. Commun. 2016, 52, 6166.
[11] Tang, T.; Chen, Y. Q.; Fu, B. S.; He, Z. Y.; Xiao, H.; Wu, F.; Wang, J. Q.; Wang, S. R.; Zhou, X. Chin. Chem. Lett. 2016, 27, 540.
[12] Zhai, Q. S.; Feng, W. Y.; Feng, G. Q. Anal. Methods 2016, 8, 5832.
[13] Chen, W.; Liu, W.; Liu, X. J.; Kuang, Y. Q.; Yu, R. Q.; Jiang, J. H. Talanta 2017, 162, 225.
[14] Li, B.; He, Z. S.; Zhou, H.; Zhang, H. H.; Liu, G. H. Dyes Pigm. 2017, 146, 300.
[15] Lu, Z. L.; Fan, W. L.; Shi, X. M.; Lu, Y. Y.; Fan, C. H. Anal. Chem. 2017, 89, 9918.
[16] Ma, J. H.; Fan, J. L.; Li, H. D.; Yao, Q. C.; Xia, J.; Wang, J. Y.; Peng, X. J. Dyes Pigm. 2017, 138, 39.
[17] Liu, C. T.; Wang, F.; Xiao, T.; Chi, B.; Wu, Y. H.; Zhu, D. R.; Chen, X. Q. Sens. Actuator, B 2018, 256, 55.
[18] Wang, S.; Ma, S. Y.; Zhang, J. D.; Sheng, M, Y.; Liu, P.; Zhang, S. Y.; Li, J. L. Sens. Actuator, B 2018, 261, 418.
[19] Fan, J. L.; Sun, W.; Hu, M. M.; Cao, J. F.; Cheng, G. H.; Dong, H. J.; Song, K. D.; Liu, Y. C.; Sun, S. G.; Peng, X. J. Chem. Commun. 2012, 48, 8117.
[20] Hu, C.; Sun, W.; Cao, J. F.; Gao, P.; Wang, J. Y.; Fan, J. L.; Song, F. L.; Sun, S. G.; Peng, X. J. Org. Lett. 2013, 15, 4022.
[21] Sun, Y.; Zhao, D.; Fan, S. W.; Duan, L. Sens. Actuator, B 2015, 208, 512.
[22] Dai, X.; Wang, Z-Y.; Du, Z-F.; Miao, J-Y.; Zhao, B-X. Sens. Actuator, B 2016, 232, 369.
[23] Xia, X. T.; Zeng, F.; Zhang, P. S.; Lyu, J.; Huang, Y.; Wu, S. Z. Sens. Actuator, B 2016, 227, 411.
[24] Yang, X. P.; Liu, Y. X.; Wu, X, L.; Zhang, D.; Ye, Y. Sens. Actuator, B 2017, 253, 488.
[25] Xu, H.; Gu, B. A.; Li, Y. Q.; Huang, Z.; Su, W.; Duan, X. L.; Yin, P.; Li, H. T.; Yao, S. Z. Talanta 2018, 180, 199.
[26] Xiao, L. L.; Tu, J.; Sun, S. G.; Pei, Z. C.; Pei, T. X.; Pang, Y.; Xu, Y. Q. RSC Adv. 2014, 4, 41807.
[27] Zhang, Y.; Liu, J. F.; Yi, R. H.; Ai, S. F.; Cheng, H. R.; Jia, W. Z. Chin. J. Anal. Chem. 2018, 46, 511(in Chinese). (张勇, 刘劲风, 益润豪, 艾思凡, 程焕仁, 贾文志, 分析化学, 2018, 46, 511.)
[28] Ju, Z. Y.; Shu, P. H.; Xie, Z. Y.; Jiang, Y. Q.; Tao, W. J.; Xu, Z. H. Chin. J. Org. Chem. 2019, 39, 697(in Chinese). (鞠志宇, 舒朋华, 谢智宇, 蒋雨晴, 陶伟杰, 许志红, 有机化学, 2019, 39, 697.)
[29] Zhai, Q. S.; Yang, S. J.; Fang, Y. L.; Zhang, H. Y.; Feng, G. Q. RSC Adv. 2015, 5, 94216.
[30] Ding, S. S.; Zhang, Q.; Xue, S. H.; Feng, G. Q. Analyst 2015, 140, 4687.
[31] Li, M. X.; Feng, W. Y.; Zhang, H. Y.; Feng, G. Q. Sens. Actuator, B 2017, 243, 51.
[32] Feng, W. Y.; Hong, J. X.; Weiyong Feng, Feng, G. Q. Sens. Actuator, B 2017, 251, 389.
[33] Feng, W. Y.; Bai, L. Y.; Jia, S. W.; Geng, G. Q. Sens. Actuator, B 2018, 260, 554.
[34] Ma. C.; Wei, C.; Li, X. Y.; Zheng, X. Y.; Chen, B.; Wang, M.; Zhang, P. Z.; Li, X. L. Dyes Pigm. 2019, 162, 624.
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