Competitive Fluorescence Sensing for Paraquat Based on Methylene Blue/Water-Soluble Phosphate Salt Pillar[5]arene
- Corresponding author: Yang Lijuan, yangljyang@sina.com
Citation:
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
Desipio, M. M.; Thorpe, R.; Saha, D. Optik 2018, 172, 1047.
doi: 10.1016/j.ijleo.2018.07.124
Siangproh, W.; Somboonsuk, T.; Chailapakul, O.; Songsrirote, K. Talanta 2017, 174, 448.
doi: 10.1016/j.talanta.2017.06.045
Hu, X.; Liang, Y.-Y.; Zhao, H.-Y.; Zhao, M. Int. Immunopharmacol. 2019, 67, 231.
doi: 10.1016/j.intimp.2018.12.029
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.
doi: 10.1038/s41467-018-05437-5
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.
doi: 10.1021/ja3099905
Wang, K.; Guo, D.-S.; Zhang, H.-Q.; Li, D.; Zheng, X-L.; Liu, Y. J. Med. Chem. 2009, 52, 6402.
doi: 10.1021/jm900811z
Zhao, Z.-Z.; Zhang, F.-W.; Zhang, Z.-P. Spectrochim. Acta A 2018, 199, 96.
doi: 10.1016/j.saa.2018.03.042
Tcheumi, H. L.; Tassontio, V. N.; Tonle, I. K.; Ngameni, E. Appl. Clay Sci. 2019, 173, 97.
doi: 10.1016/j.clay.2019.03.013
Rai, M. K.; Das, J. V.; Gupta, V. K. Talanta 1997, 45, 343.
doi: 10.1016/S0039-9140(97)00136-7
Lu, T.; Birke, R. L.; Lombardi, J. R. Langmuir 1986, 2, 305.
doi: 10.1021/la00069a009
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.
doi: 10.1016/0021-9673(94)00889-2
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.
doi: 10.1016/j.jchromb.2013.10.028
Tomková, H.; Sokolová, R.; Opletal, T.; Kučerová, P.; Kučera, L.; Součková, J.; Skopalová, J.; Barták, P. J. Electroanal. Chem. 2018, 821, 33.
doi: 10.1016/j.jelechem.2017.12.048
Vinner, E.; Stievenart, M.; Humbert, L.; Mathieu, D. Biomed. Chromatogr. 2001, 15, 342.
doi: 10.1002/bmc.81
Usui, K.; Minami, E.; Fujita, Y.; Kobayashi, H.; Hanazaw, T.; Kamijo, Y.; Funayama, M. J. Pharmacol. Toxicol. Methods 2019, 100, 106610.
doi: 10.1016/j.vascn.2019.106610
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.
doi: 10.1021/acsomega.9b02180
Du, T.; Yuan, W.; Zhao, Z. Y.; Liu, S. M. Chem. Commun. 2019, 55, 3658.
doi: 10.1039/C9CC00406H
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.
doi: 10.1016/j.bios.2018.12.020
Chen, Y.; Huang, F.-H.; Li, Z.-T.; Liu, Y. Sci. China Chem. 2018, 61, 979.
doi: 10.1007/s11426-018-9337-4
Huo, B.-C.; Li, B.; Su, H.; Zeng, X. Q.; Xu, K.-D.; Cui, L. Chin. J. Org. Chem. 2019, 39, 1990(in Chinese).
Sun, C.-L.; Teng, K.-X.; Niu, L.-Y.; Chen, Y.-Z.; Yang, Q.-Z. Acta Chim. Sinica 2018, 76, 779.
doi: 10.6023/A18070258
Li, P.-Y.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2019, 30, 1190.
doi: 10.1016/j.cclet.2019.03.035
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.
doi: 10.1016/j.cclet.2018.10.014
Li, Z.-T.; Yang, J.; Huang, F.-H. Chin. J. Chem. 2018, 36, 59.
doi: 10.1002/cjoc.201700601
Jie, K.-C.; Zhou, Y.-J.; Li, E.-R.; Huang, F.-H. Acc. Chem. Res. 2018, 51, 2064.
doi: 10.1021/acs.accounts.8b00255
Shao, W.; Liu, X.; Wang, T.-T.; Hu, X.-Y. Chin. J. Org. Chem. 2018, 38, 1107(in Chinese).
Pian, M. D.; Schalley, C. A.; Fabris, F.; Scarso, A. Org. Chem. Front. 2019, 6, 1044.
doi: 10.1039/C9QO00176J
Cao, D.-R.; Herbert, M. Chin. Chem. Lett. 2019, 30, 1758.
doi: 10.1016/j.cclet.2019.06.026
Zhang, Z.-B.; Sun, K.-C.; Li, S.-J.; Yu, G.-C. Chin. Chem. Lett. 2019, 30, 957.
doi: 10.1016/j.cclet.2019.01.018
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.
doi: 10.1016/j.talanta.2018.11.099
Qian, X. C.; Zhou, X. J.; Gao, W.; Li, J.; Ran, X.; Du, G. B.; Yang, L. Microchem. J. 2019, 150, 104203.
doi: 10.1016/j.microc.2019.104203
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.
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.
doi: 10.1016/j.matt.2019.03.005
Sun, S.-G.; Li, F.-S.; Liu, F.-Y.; Wang, J.-T.; Peng, X.-J. Sci. Rep. 2014, 4, 3570.
Mao, X.-W.; Liu, T.; Bi, J.-H.; Luo, L.; Tian, D.-M.; Li, H.-B. Chem. Commun. 2016, 52, 4385.
doi: 10.1039/C6CC00949B
Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
doi: 10.1021/ja711260m
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).
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).
Wang, X.; Wu, J.-R.; Liang, F.; Yang, Y.-W. Org. Lett. 2019, 21, 5215.
doi: 10.1021/acs.orglett.9b01827
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.
doi: 10.1016/j.dyepig.2019.01.049
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).
Venkatesan, M.; Sathiyanarayanan, K. I. Sens. Actuators B 2018, 267, 373.
doi: 10.1016/j.snb.2018.03.077
Huang, X.; Wu, S.-S.; Ke, X.-K.; Li, X.-Y.; Du, X.-Z. ACS Appl. Mater. Interfaces 2017, 9, 19638.
doi: 10.1021/acsami.7b04015
Cui, S.-Y.; Du, J.-L.; Wang, T.; Hu, X.-L. Spectrochim. Acta A 2012, 96, 188.
doi: 10.1016/j.saa.2012.05.025
Zhou, Y.-Y.; Yu, H.-P.; Zhang, L.; Xu, H.-W.; Wu, L.; Sun, J.-Y.; Wang, L. Microchim. Acta 2009, 164, 63.
doi: 10.1007/s00604-008-0032-3
Montes-Navajas P., Corma, A.; Garcia, H. Chem. Phys. Chem. 2008, 9, 713.
doi: 10.1002/cphc.200700735
Lu, Q.; Gu, J.-H.; Yu, H.-P.; Liu, C.; Wang, L.; Zhou, Y.-Y. Spectrochim. Acta A 2007, 68, 15.
doi: 10.1016/j.saa.2006.10.044
Zhao, G.-C.; Zhu, J.-J.; Chen, H.-Y. Spectrochim. Acta A 1999, 55, 1109.
doi: 10.1016/S1386-1425(99)00002-5
Yang, K.; Wen, J.; Chao, S.; Liu, J.; Yang, K.; Pei, Y.-X.; Pei, Z.-C. Chem. Commun. 2018, 54, 5911.
doi: 10.1039/C8CC02739K
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.
doi: 10.1016/j.tet.2018.06.006
Siangproh, W.; Somboonsuk, T.; Chailapakul, O.; Songsrirote, K. Talanta 2017, 174, 448.
doi: 10.1016/j.talanta.2017.06.045
Chuntib, P.; Themsirimongkon, S.; Saipanya, S.; Jakmunee, J. Talanta 2017, 170, 1.
doi: 10.1016/j.talanta.2017.03.073
Zhao, Z.-Z.; Zhang, F.-W.; Zhang, Z.-P. Spectrochim. Acta A 2018, 199, 96.
doi: 10.1016/j.saa.2018.03.042
Chuntib, P.; Jakmunee, J. Talanta 2015, 144, 432.
doi: 10.1016/j.talanta.2015.06.066
Tu, J.; Xiao, L.-L.; Jiang, Y.-F.; He, Q.-Y.; Sun, S.-G.; Xu, Y.-Q. Sens. Actuators B 2015, 215, 382.
doi: 10.1016/j.snb.2015.04.015
Chen, C.-R.; Men, G.-G.; Bu, W.-H.; Liang, C.-S.; Sun, H.-C.; Jiang, S.-M. Sens. Actuators B 2015, 220, 463.
doi: 10.1016/j.snb.2015.06.004
Hu, S. M.S. Thesis, Hebei University of Science and Technology, Shijiazhuang, 2011 (in Chinese).
Grandis, V. D.; Bizzarri, A. R.; Cannistraro, S. J. Mol. Recognit. 2007, 20, 215.
doi: 10.1002/jmr.840
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.
doi: 10.1021/acs.chemmater.6b00691
Yao, Y. Ph.D. Dissertation, Zhejiang University, Hangzhou, 2015 (in Chinese).
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.
doi: 10.1002/jcc.21256
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PP5A (20 mmol·L-1), MB (20 mmol·L-1), MB/PP5A (20 mmol·L-1 MB+20 mmol·L-1 PP5A), MB/PP5A+PQ (20 mmol·L-1 MB+20 mmol·L-1 PP5A+20 mmol·L-1 PQ), PQ (20 mmol·L-1), PQ/PP5A (20 mmol·L-1 PQ+20 mmol·L-1 PP5A). The cartoon illustration is consistent with the corresponding structure in Scheme 1
(A) PP5A (0.015 mmol·L-1), MB (0.015 mmol·L-1), MB/PP5A (0.015 mmol·L-1 MB+0.015 mmol·L-1 PP5A); (B) PP5A (0.04 mmol·L-1)、PQ (0.04 mmol·L-1)、PQ/PP5A (0.04 mmol·L-1 PQ+0.04 mmol·L-1 PP5A)
(A) MB/PP5A+amino acids or anions; (B) MB/PP5A+PQ+amino acids, anions, cations or analogs
PQ-1 and MB-1 represent front view, and PQ-2 and MB-2 represent top view