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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1680 - 1688

DOI: https://doi.org/10.6023/cjoc201911008

Competitive Fluorescence Sensing for Paraquat Based on Methylene Blue/Water-Soluble Phosphate Salt Pillar[5]arene

  • Yang Yunhan ,
  • Bao Qiulian ,
  • Luo Jianping ,
  • Yang Junli ,
  • Li Canhua ,
  • Wei Keke ,
  • Chuan Yongming ,
  • Yang Lijuan
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  • Key Laboratory of Intelligent Supramolecular Chemistry at the University of Yunnan Province, National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry & Environment, Yunnan Minzu University, Kunming 650500

Received date: 2019-11-06

  Revised date: 2019-12-18

  Online published: 2020-03-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21562048, 21762051), the Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province and the Science Research Fund Project of Yunnan Provincial Department of Education (No. 2019Y0193).

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Abstract

Using water-soluble phosphate salt pillar[5]arene (PP5A) as the host and indicate dye methylene blue (MB) as the guest, the MB/PP5A host-guest inclusion complex was constructed. The fluorescence properties, complexation constants, complexation ratios and binding modes of PP5A and MB were studied. The inclusion complex was applied to competitive fluorescent sensing of paraquat (PQ). When MB is complexed with PP5A receptor, its fluorescence is quenched. When PQ is added to the MB/PP5A sensing system, PQ competes into the cavity of PP5A and MB is detached from the cavity of PP5A, which led to fluorescence recovery. This enables competitive fluorescence sensing of PQ. Therefore, the MB/PP5A fluorescence sensing system can detect PQ sensitively with a minimum detection limit of 3.6×10-7mol·L-1. The probe has the advantages of strong selectivity, simple and fast preparation, response in a wide pH range and good anti-interference performance, and can provide the basis for the sensing detection of PQ in organisms and environments.

Key words： water-soluble phosphate salt pillar[5]arene; methylene blue; inclusion complex; competitive recognition; paraquat

Cite this article

Yang Yunhan , Bao Qiulian , Luo Jianping , Yang Junli , Li Canhua , Wei Keke , Chuan Yongming , Yang Lijuan . Competitive Fluorescence Sensing for Paraquat Based on Methylene Blue/Water-Soluble Phosphate Salt Pillar[5]arene[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1680 -1688 . DOI: 10.6023/cjoc201911008

References

[1] Desipio, M. M.; Thorpe, R.; Saha, D. Optik 2018, 172, 1047.
[2] Siangproh, W.; Somboonsuk, T.; Chailapakul, O.; Songsrirote, K. Talanta 2017, 174, 448.
[3] Hu, X.; Liang, Y.-Y.; Zhao, H.-Y.; Zhao, M. Int. Immunopharmacol. 2019, 67, 231.
[4] Gao, C.; Huang, Q.-X.; Lan, Q.-P.; Feng, Y.; Tang, F.; Hoi, M. P. M.; Zhang;, J.-X.; Lee S. M. Y.; Wang, R.-B. Nat. Commun. 2018, 9, 2967.
[5] Yu, G.-C.; Zhou, X.-Y.; Zhang, Z.-B.; Han, C.-Y.; Mao, Z.-W.; Gao, C.-Y.; Huang, F.-H. J. Am. Chem. Soc. 2012, 134, 19489.
[6] Wang, K.; Guo, D.-S.; Zhang, H.-Q.; Li, D.; Zheng, X-L.; Liu, Y. J. Med. Chem. 2009, 52, 6402.
[7] Zhao, Z.-Z.; Zhang, F.-W.; Zhang, Z.-P. Spectrochim. Acta A 2018, 199, 96.
[8] Tcheumi, H. L.; Tassontio, V. N.; Tonle, I. K.; Ngameni, E. Appl. Clay Sci. 2019, 173, 97.
[9] Rai, M. K.; Das, J. V.; Gupta, V. K. Talanta 1997, 45, 343.
[10] Lu, T.; Birke, R. L.; Lombardi, J. R. Langmuir 1986, 2, 305.
[11] Kambhampati, I.; Roinestad, K. S.; Hartman, T. G.; Rosen, J. D.; Fukuda, E. K.; Lippincott, R. L.; Rosen, R. T. J. Chromatogr. A 1994, 688, 67.
[12] Gao, L.; Liu, J.-T.; Wang, C.-Y.; Liu, G.-J.; Niu, X.-D.; Shu, C.-X.; Zhu, J. J. Chromatogr. B 2014, 944, 136.
[13] Tomková, H.; Sokolová, R.; Opletal, T.; Kučerová, P.; Kučera, L.; Součková, J.; Skopalová, J.; Barták, P. J. Electroanal. Chem. 2018, 821, 33.
[14] Vinner, E.; Stievenart, M.; Humbert, L.; Mathieu, D. Biomed. Chromatogr. 2001, 15, 342.
[15] Usui, K.; Minami, E.; Fujita, Y.; Kobayashi, H.; Hanazaw, T.; Kamijo, Y.; Funayama, M. J. Pharmacol. Toxicol. Methods 2019, 100, 106610.
[16] Yang, Y.-H.; Yang, J.-L.; Du, Y.; Li C.-H.; Wei K.-K.; Lu, J.-J.; Chen, W.; Yang, L.-J. ACS Omega 2019, 4, 17741.
[17] Du, T.; Yuan, W.; Zhao, Z. Y.; Liu, S. M. Chem. Commun. 2019, 55, 3658.
[18] Xie, Z.-P.; Lei, J.-L.; Yang, M.-F.; Li, Y.-J.; Geng, X.-H.; Liu, S.-M.; Wang, J.-H. Biosens. Bioelectron. 2019, 127, 200.
[19] Chen, Y.; Huang, F.-H.; Li, Z.-T.; Liu, Y. Sci. China Chem. 2018, 61, 979.
[20] Huo, B.-C.; Li, B.; Su, H.; Zeng, X. Q.; Xu, K.-D.; Cui, L. Chin. J. Org. Chem. 2019, 39, 1990(in Chinese). (霍博超, 李斌, 苏杭, 曾宪强, 徐凯迪, 崔雷, 有机化学, 2019, 39, 1990.)
[21] Sun, C.-L.; Teng, K.-X.; Niu, L.-Y.; Chen, Y.-Z.; Yang, Q.-Z. Acta Chim. Sinica 2018, 76, 779.
[22] Li, P.-Y.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2019, 30, 1190.
[23] Wang, M.-J.; Du, X.-S.; Tian, H.-S.; Jia, Q.; Deng, R.; Cui, Y.-H.; Wang, C. Y; Kamel, M. Chin. Chem. Lett. 2019, 30, 345.
[24] Li, Z.-T.; Yang, J.; Huang, F.-H. Chin. J. Chem. 2018, 36, 59.
[25] Jie, K.-C.; Zhou, Y.-J.; Li, E.-R.; Huang, F.-H. Acc. Chem. Res. 2018, 51, 2064.
[26] Shao, W.; Liu, X.; Wang, T.-T.; Hu, X.-Y. Chin. J. Org. Chem. 2018, 38, 1107(in Chinese). (绍为, 刘昕, 王婷婷, 胡晓玉, 有机化学, 2018, 38, 1107.)
[27] Pian, M. D.; Schalley, C. A.; Fabris, F.; Scarso, A. Org. Chem. Front. 2019, 6, 1044.
[28] Cao, D.-R.; Herbert, M. Chin. Chem. Lett. 2019, 30, 1758.
[29] Zhang, Z.-B.; Sun, K.-C.; Li, S.-J.; Yu, G.-C. Chin. Chem. Lett. 2019, 30, 957.
[30] Tan, X.-P.; Wu, Y.; Yu, S.; Zhang, T.-Y.; Tian, H.-X.; He, S.-H.; Zhao, A.-N.; Chen, Y.-W.; Gou, Q. Talanta 2019, 195, 472.
[31] Qian, X. C.; Zhou, X. J.; Gao, W.; Li, J.; Ran, X.; Du, G. B.; Yang, L. Microchem. J. 2019, 150, 104203.
[32] Li, H. Chen, D.-X.; Sun, Y.-L.; Zheng, Y.-B.; Tan, L.-L.; Weiss, P.-S.; Yang, Y.-W. J. Am. Chem. Soc. 2013, 135, 1570.
[33] Wang, X.; Liu, Z. J.; Hill, E. H.; Zheng, Y. B.; Guo, G. Q.; Wang, Y.; Weiss, P. S.; Yu, J. H.; Yang, Y. W. Matter 2019, 1, 848.
[34] Sun, S.-G.; Li, F.-S.; Liu, F.-Y.; Wang, J.-T.; Peng, X.-J. Sci. Rep. 2014, 4, 3570.
[35] Mao, X.-W.; Liu, T.; Bi, J.-H.; Luo, L.; Tian, D.-M.; Li, H.-B. Chem. Commun. 2016, 52, 4385.
[36] Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[37] Shi, H.-X.; Cheng, X.-B.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Wei, T.-B. Chin. J. Org. Chem. 2018, 38, 1718(in Chinese). (师海雄, 程晓斌, 林奇, 姚虹, 张有明, 魏太保, 有机化学, 2018, 38, 1718.)
[38] Li, Z.-Y.; Hou, N.-N.; Shao, W.; Xiao, S.-J.; Lin, C.; Wang, L.-Y. Chin. J. Org. Chem. 2018, 38, 2002(in Chinese). (李臻益, 候娜娜, 邵为, 肖守军, 林晨, 王乐勇, 有机化学, 2018, 38, 2002.)
[39] Wang, X.; Wu, J.-R.; Liang, F.; Yang, Y.-W. Org. Lett. 2019, 21, 5215.
[40] Ma, X.-Q.; Wang, Y.; Wei, T.-B.; Qi, L.-H.; Jiang, X.-M.; Ding, J.-D.; Zhu, W.-B.; Yao, H.; Zhang, Y.-M.; Lin, Q. Dyes Pigm. 2019, 164, 279.
[41] Chen, J.-F.; Liu, X.; Han, B.-B.; Ding, J.-D.; Zhang, Y.-M.; Lin, Q.; Yao, H.; Wei, T.-B. Chin. J. Org. Chem. 2018, 38, 2741(in Chinese). (陈进发, 刘茜, 韩冰冰, 丁金东, 张有明, 林奇, 姚虹, 魏太保, 有机化学, 2018, 38, 2741.)
[42] Venkatesan, M.; Sathiyanarayanan, K. I. Sens. Actuators B 2018, 267, 373.
[43] Huang, X.; Wu, S.-S.; Ke, X.-K.; Li, X.-Y.; Du, X.-Z. ACS Appl. Mater. Interfaces 2017, 9, 19638.
[44] Cui, S.-Y.; Du, J.-L.; Wang, T.; Hu, X.-L. Spectrochim. Acta A 2012, 96, 188.
[45] Zhou, Y.-Y.; Yu, H.-P.; Zhang, L.; Xu, H.-W.; Wu, L.; Sun, J.-Y.; Wang, L. Microchim. Acta 2009, 164, 63.
[46] Montes-Navajas P., Corma, A.; Garcia, H. Chem. Phys. Chem. 2008, 9, 713.
[47] Lu, Q.; Gu, J.-H.; Yu, H.-P.; Liu, C.; Wang, L.; Zhou, Y.-Y. Spectrochim. Acta A 2007, 68, 15.
[48] Zhao, G.-C.; Zhu, J.-J.; Chen, H.-Y. Spectrochim. Acta A 1999, 55, 1109.
[49] Yang, K.; Wen, J.; Chao, S.; Liu, J.; Yang, K.; Pei, Y.-X.; Pei, Z.-C. Chem. Commun. 2018, 54, 5911.
[50] Wang, L.; Fan, Y.-Q.; Guan, X.-W.; Qu, W.-J.; Lin, Q.; Yao, H.; Wei, T.-B.; Zhang, Y.-M. Tetrahedron 2018, 74, 4005.
[51] Siangproh, W.; Somboonsuk, T.; Chailapakul, O.; Songsrirote, K. Talanta 2017, 174, 448.
[52] Chuntib, P.; Themsirimongkon, S.; Saipanya, S.; Jakmunee, J. Talanta 2017, 170, 1.
[53] Zhao, Z.-Z.; Zhang, F.-W.; Zhang, Z.-P. Spectrochim. Acta A 2018, 199, 96.
[54] Chuntib, P.; Jakmunee, J. Talanta 2015, 144, 432.
[55] Tu, J.; Xiao, L.-L.; Jiang, Y.-F.; He, Q.-Y.; Sun, S.-G.; Xu, Y.-Q. Sens. Actuators B 2015, 215, 382.
[56] Chen, C.-R.; Men, G.-G.; Bu, W.-H.; Liang, C.-S.; Sun, H.-C.; Jiang, S.-M. Sens. Actuators B 2015, 220, 463.
[57] Hu, S. M.S. Thesis, Hebei University of Science and Technology, Shijiazhuang, 2011 (in Chinese). (胡硕, 硕士论文, 河北科技大学, 石家庄, 2011.)
[58] Grandis, V. D.; Bizzarri, A. R.; Cannistraro, S. J. Mol. Recognit. 2007, 20, 215.
[59] Hu, X.-Y.; Liu, X.; Zhang, W.-Y.; Qin, S.-Yao, C. H.; Li, Y.; Cao, D.-R.; Peng, L.-M.; Wang, L.-Y. Chem. Mater. 2016, 28, 3778.
[60] Yao, Y. Ph.D. Dissertation, Zhejiang University, Hangzhou, 2015 (in Chinese). (姚勇, 博士论文, 浙江大学, 杭州, 2015.)
[61] Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785.
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