ARTICLE

A Novel Imidazophenazine Lactam Reaction Type Recognition Cyanide Ion Fluorescence Probe

  • Li Xiang ,
  • Lin Qi ,
  • Qu Wenjuan ,
  • Li Qiao ,
  • Chen Xiaobin ,
  • Li Wenting ,
  • Zhang Youming ,
  • Yao Hong ,
  • Wei Taibao
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  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received date: 2016-11-03

  Revised date: 2016-12-29

  Online published: 2017-01-17

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21662031, 21661028, 21574104, 21262032).

Abstract

A novel imidazophenazine lactam fluorescence chemosensor (S1) was designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS techniques. Fluorescence spectra of S1 in dimethyl sulfoxide (DMSO) solution were measured. Its maximum emission wavelength was 524 nm. The DMSO solution of S1 has bright yellow fluorescence. Respectively, to the S1 solution add F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4-, ClO4-, and SCN-, the fluorescent color of the solution didn't change. Only the CN- addition, the fluorescent color of the S1 solution changed from yellow to orange-red, indicating that S1 has good specific selectivity for CN-. The results of anti-disturbance experiment demonstrated that S1 detect CN- without interference from other anions. By calculation, the linear of the fluorescence of the sensor for CN- is 9.96×10-7. This value is lower than the World Health Organization (WHO) provisions of the cyanide content of drinking water. Mechanism studies show that S1 is a fluorescence sensor by reactive recognition CN-. In addition, the application of sensor S1 supported on solid silica gel was used as a solid material to detecting solid NaCN and CN- in pure water.

Cite this article

Li Xiang , Lin Qi , Qu Wenjuan , Li Qiao , Chen Xiaobin , Li Wenting , Zhang Youming , Yao Hong , Wei Taibao . A Novel Imidazophenazine Lactam Reaction Type Recognition Cyanide Ion Fluorescence Probe[J]. Chinese Journal of Organic Chemistry, 2017 , 37(4) : 889 -895 . DOI: 10.6023/cjoc201611008

References

[1] Chen, J.-J.; Chen, W.; He, H.; Li, D.-B.; Li, W.-W.; Xiong, L.; Yu, H.-Q. Environ. Sci. Technol. 2013, 47, 1033.
[2] Ahuja, E. G.; Janning, P.; Mentel, M.; Graebsch, A.; Breinbauer, R.; Hiller, W.; Costisella, B.; Thomashow, L. S.; Mavrodi, D. V.; Blankenfeldt, W. J. Am. Chem. Soc. 2008, 130, 17053.
[3] Yang, L.; Li, X.; Qu, Y.; Qu, W.-S.; Zhang, X.; Hang, Y.-D.; Agren, H.; Hua, J.-L. Sen. Actuators, B 2014, 203, 833.
[4] Gu, P.-Y.; Zhao, Y.-B.; He, J.-H.; Zhang, J.; Wang, C.-Y.; Xu, Q.-F.; Lu, J.-M.; Sun, X.-W.; Zhang, Q.-C. J. Org. Chem. 2015, 80, 3030.
[5] Chen, W.; Su, J.-H,; Tian, H. Sci. China: Chem. 2016, 46, 325 (in Chinese).
(陈薇, 苏建华, 田禾, 中国科学: 化学, 2016, 46, 325.)
[6] Zhou, H.-T.; Sun, L.; Chen, W.; Tian, G.-J.; Chen, Y.; Li, Y.-R.; Su. J.-H. Tetrahedron 2016, 72, 2300.
[7] Metz, A. E.; Podlesny, E. E.; Carroll, P. J.; Klinghoffer, A. N.; Kozlowski, M. C. J. Am. Chem. Soc. 2014, 136, 10601.
[8] Aggarwal, K.; Khurana, J. M. J. Lumin. 2015, 167, 146.
[9] Wei, T.-B.; Wu, G.-Y.; Shi, B.-B.; Lin,-Q.; Yao, H.; Zhang, Y.-M. Chin. J. Chem. 2014, 32, 1238.
[10] Zhang, P.; Zhang, Y.-M.; Lin, Q.; Yao, H.; Wei, T.-B. Chin. J. Org. Chem. 2014, 34, 1300 (in Chinese).
(张鹏, 张有明, 林奇, 姚虹, 魏太保, 有机化学, 2014, 34, 1300.)
[11] Li, C.-W.; Yang, D.; Yin, B.; Guo, Y. Chin. J. Org. Chem. 2016, 36, 787 (in Chinese).
(李长伟, 杨栋, 尹兵, 郭媛, 有机化学, 2016, 36, 787.)
[12] Gao, G.-B.; Gong, D.-J.; Zhang, M.-X.; Sun, T.-L. Acta. Chim. Sinica. 2016, 74, 363 (in Chinese).
(高冠斌, 龚德君, 张明曦, 孙涛垒, 化学学报, 2016, 74, 363.)
[13] Zhang, Y.-P.; You, C.-X.; Yang, Y.-S.; Liu, X.-Y.; Guo, H.-C.; Dong, Y.-Y. Chin. J. Org. Chem. 2016, 36, 1401 (in Chinese).
(张应鹏, 尤彩霞, 杨云裳, 刘小育, 郭慧琛, 董玉莹, 有机化学, 2016, 36, 1401.)
[14] Su, N.; Yang, M.-P.; Meng, W.-P.; Yang, B.-Q. Chin. J. Org. Chem. 2015, 35, 175 (in Chinese).
(苏娜, 杨美盼, 孟文斐, 杨秉勤, 有机化学, 2015, 35, 175.)
[15] Yu, H.-B.; Li, H.-L.; Zhang, X.-F.; Xiao, Y.; Fang, P.-J.; Lü, C.-J.; Hou, W. Acta Chim. Sinica 2015, 73, 450 (in Chinese).
(于海波, 李红玲, 张新富, 肖义, 方沛菊, 吕春娇, 侯伟, 化学学报, 2015, 73, 450.)
[16] Zang, L.-B.; Wei, D.-Y.; Wang, S.-C.; Jiang, S.-M. Tetrahedron 2012, 68, 636.
[17] Gupta, A. S.; Garg, A.; Paul, K.; Luxami, V. J. Lumin. 2016, 173, 165.
[18] Jo, J. Y.; Olasz, A.; Chen, C. H.; Lee, D. J. Am. Chem. Soc. 2013, 135, 3620.
[19] Yan, L.-R.; Yang, M.-P.; Leng, X.; Zhang, M.; Long, Y.; Yang, B.-Q. Tetrahedron 2016, 72, 4361.
[20] Yoo, M.; Park, S.; Kim, H. J. Sen. Actuators, B 2015, 220, 788.
[21] Kim, D.; Na, S.; Y.; Kim, H. J. Sen. Actuators, B 2016, 226, 227.
[22] Wang, S. T.; Chir, J. L.; Jhong, Y.; Wu, A. T. J. Lumin. 2015, 167, 413.
[23] Yang, L.; Li, X.; Yang, J.-B.; Qu, Y.; Hua, J.-L. ACS Appl. Mater. Interfaces 2013, 5, 1317.
[24] Yang, L.; Zhang, X.; Qu, W.-S.; Hua, J.-L. Imaging Sci. Photochem. 2014, 32, 1 (in Chinese).
(杨林, 张潇, 瞿卫松, 花建丽, 影像科学与光化学, 2014, 32, 1.)
[25] Wang, F.; Wang, L.; Chen, X. Q.; Yoon, J. Y. Chem. Soc. Rev. 2014, 43, 12.
[26] Dagiliene, M.; Martynaitis, V.; Krisiucniene, V.; Krikstolaityte, S.; Sackus, A. ChemistryOpen 2015, 4, 363.
[27] Wang, K.-N.; Ma, L.; Liu, G.-Q.; Cao, D.-X.; Guan, R.-F.; Liu, Z.-Q. Dyes Pigm. 2016, 126, 104.
[28] Lee, K. S.; Kim, H. J.; Kim, G. H.; Shin, I.; Hong, J. I. Org. Lett. 2008, 10, 49.
[29] El-Shishtawy, R. M.; Al-Zahrani, F. A. M.; Al-amshany, Z. M.; Asiri, A. M. Sen. Actuators, B 2017, 240, 288.
[30] Meng, Q.-T. Ph.D. Dissertation, Dalian University of Technology, Dalian, 2011 (in Chinese).
(孟庆涛, 博士论文, 大连理工大学, 大连, 2011.)
[31] Shi, B.-B.; Zhang, P.; Wei, T.-B.; Yao, H.; Lin, Q.; Liu, J.; Zhang, Y.-M. Tetrahedron 2013, 69, 7981.
[32] Shi, B.-B.; Zhang, Y.-M.; Wei, T.-B.; Lin, Q.; Yao, H.; Zhang, P.; You, X.-M. Sens. Actuators, B 2014, 190, 555.
[33] Lin, Q.; Zhu, X.; Chen, P.; Fu, Y. P.; Zhang, Y. M.; Wei, T. B. Acta Chim. Sinica 2013, 71, 1516 (in Chinese).
(林奇, 朱鑫, 陈佩, 符永鹏, 张有明, 魏太保, 化学学报, 2013, 71, 1516.)
[34] Gao, G.-Y.; Qu, W.-J.; Shi, B.-B.; Lin, Q.; Yao, H.; Yang, W.-L.; Zhang, Y.-M.; Wei, T.-B. Spectrochim. Acta, Part A 2014, 121, 514.
[35] Gao, G.-Y.; Qu, W.-J.; Shi, B.-B.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Chang, J.; Cai, Y.; Wei, T.-B. Sens. Actuators, B 2015, 213, 501.
[36] Hu, J.-Y.; Liu, R.; Zhu, X.-L.; Cai, X.; Zhu, H.-J. Chin. Chem. Lett. 2015, 26, 339.
[37] Wei, T.-B.; Li, W.-T.; Li, Q.; Su, J.-X.; Qu, W.-J. Lin, Q.; Yao, H.; Zhang, Y.-M. Tetrahedron Lett. 2016, 57, 2767.
[38] Wei, T.-B.; Li, W.-T.; Li, Q.; Qu, W.-J.; Li, H.; Yan, G.-T.; Lin, Q.; Yao, H.; Zhang, Y.-M. RSC Adv. 2016, 6, 43832.
[39] Li, W.-T.; Wu, G.-Y.; Qu, W.-J.; Li, Q.; Lou, J.-C.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Wei, T.-B. Sens. Actuators, B 2017, 239, 671.
[40] Zhang, Y.-M.; Wang, Y.-L.; Lin, Q.; Wang, D.-D.; Wei, T.-B. Chin. J. Org. Chem. 2009, 29, 575 (in Chinese).
(张有明, 王雅琳, 林奇, 王丹丹, 魏太保, 有机化学, 2009, 29, 575.)
[41] Wei, T.-B.; Wang, J.; Luo, R.; Zhang, Y.-M. Chin. J. Org. Chem. 2007, 27, 1381 (in Chinese).
(魏太保, 王军, 罗榕, 张有明, 有机化学, 2007, 27, 1381.)
[42] Zhao, J.; Li, J.; Gao, J.; Kjelleberg, S. L. A.; Loo, S. C. J.; Zhang, Q. J. Heterocycl. Chem. 2015, 52, 1699.
[43] Sahoo, P. K.; Giri, C.; Haldar, T. S.; Puttreddy, R.; Rissanen, K.; Mal, P. Eur. J. Org. Chem. 2016, 1283.
[44] Liu, X, X.; Weinert, Z. J.; Sharafi, M.; Liao, C. Y.; Li, J. N.; Schneebeli, S. T. Angew. Chem., Int. Ed. 2015, 54, 12772.
[45] Miao, S. B.; Bangcuyo, C. G.; Smith, M. D.; Bunz, U. H. F. Angew Chem., Int. Ed. 2006, 118, 677.
[46] Wu, J.-S.; Rui, X.-H.; Long, G.-K.; Chen, W.-Q.; Yan, Q.-Y.; Zhang, Q.-C. Angew. Chem., Int. Ed. 2015, 54, 7354.
[47] Hu, J. W.; Zhang, G. H.; Shih, H. H.; Jiang, X. Q.; Suna, P. P.; Cheng, C. H. J. Organomet. Chem. 2008, 693, 2798.
[48] Lucas, M.-D.; Wang, J.-F.; Nick, A.; Li, H.; Liu, T-B.; Pang, Y. J. Phys. Chem. B 2016, 120, 766.
[49] Yang, J.-R.; Fang, H.-P.; Gao, Y. J. Phys. Chem. Lett. 2016, 7, 1788.
[50] Zhou, H.-T.; Sun, L.; Chen, W.; Tian, G.-J.; Chen, Y.; Li, Y.-R.; Su, J.-H. Tetrahedron 2016, 72, 2300.
[51] Zhou, H.-T.; Mei, J.; Chen, Y.-A.; Chen, C.-L.; Chen, W.; Zhang, Z.-Y.; Su, J.-H.; Chou, P.-T.; Tian, H. Small 2016, 12, 6542.
[52] Yang, Y.-T.; Yin, C.-X.; Huo, F.-J.; Chao, J.-B.; Zhang, Y.-B.; Cheng, F.-Q. Sens. Actuators, B 2014, 193, 220.
[53] Li, Q.; Zhang, J.-H.; Cai, Y.; Qu, W.-J.; Gao, G.-Y.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Wei, T.-B. Tetrahedron 2015, 71, 857.
[54] Shive, M.-S.-C.; Tanuja, B.; Bhaskar, G. Tetrahedron Lett. 2008, 49, 6646.
[55] Celso, R. N.; Leandro, G. N.; Vanderlei, G. M. Anal. Chem. 2015, 87, 362.
[56] Ji, H. K.; Seong, Y. L.; Hye, M. A.; Cheal, K. Sens. Actuators, B 2017, 242, 25.
[57] Duan, Y.-L.; Zheng, Y.-S. Talanta 2013, 107, 332.
[58] Shi, B.-B. M.S. Thesis, Northwest Normal University, Lanzhou, 2014 (in Chinese).
(史兵兵, 硕士论文, 西北师范大学, 兰州, 2014.)

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