Chinese Journal of Organic Chemistry >
Tetraphenylethylene-Based Tetradentate Azolium Salts: Synthesis and Selective Recognition for Ions
Received date: 2021-03-05
Revised date: 2021-03-24
Online published: 2021-07-06
Supported by
Tianjin Natural Science Foundation(18JCZDJC99600); National Natural Science Foundation of China(21572159); Program for Innovative Research Team in University of Tianjin(TD13-5074)
Two new tetraphenylethylene-based tetradentate azolium salts, 1,1,2,2-tetrakis{[2'-(N-methyl-imidazolium-1-yl)ethoxyl]phenyl}ethylene hexafluorophosphate (1) and 1,1,2,2-tetrakis{[2'-(N-picolyl-benzimidazolium-1-yl)ethoxyl]phenyl}ethylene hexafluorophosphate (2), were synthesized and characterized. Recognitions of 1 for anions and 2 for cations were studied through fluorescence spectra, UV/vis spectra, HRMS, 1H NMR and infrared spectroscopies. The results revealed that 1 was able to differentiate $H_{2}PO_{4}^-$ from other anions, and 2 was able to differentiate Ag+ from other cations via fluorescence method.
Key words: tetraphenylethylene; azolium salts; fluorescence; recognition; ions
Xinying Li , Zhixiang Zhao , Linhai Hu , Dengche Wei , Qingxiang Liu . Tetraphenylethylene-Based Tetradentate Azolium Salts: Synthesis and Selective Recognition for Ions[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3608 -3616 . DOI: 10.6023/cjoc202103011
[1] | Li, J.; Yang, X. P.; Zhang, D.; Liu, Y. X.; Tang, J.; Li, Y.; Zhao, Y. F.; Ye, Y. Sens. Actuators, B 2018, 265, 84. |
[2] | Yang, X. P.; Wang, Y. S.; Liu, R.; Zhang, Y. R.; Tang, J.; Yang, E. B.; Zhang, D.; Zhao, Y, F.; Ye, Y. Sens. Actuators, B 2019, 288, 217. |
[3] | Huang, K.; Yue, Y. X.; Jiao, X. J.; Liu, C.; Wang, Q.; He, S.; Zhao, L. C.; Zeng, X. S. Dyes Pigm. 2017, 143, 379. |
[4] | Jiao, X. J.; Liu, C.; He, S.; Zhao, L. C.; Zeng, X. S. Dyes Pigm. 2019, 160, 86. |
[5] | Jiang, X. D.; Zhao, J. L.; Li, Q.; Sun, C. L.; Guan, J.; Sun, G. T.; Xiao, L. J. Dyes Pigm. 2016, 125, 136. |
[6] | Fang, T.; Jiang, X. D.; Sun, C. L.; Li, Q. Sens. Actuators, B 2019, 290, 551. |
[7] | Qu, W.; Fang, H.; Huang, Q.; Zhang, Y.; Lin, Q.; Yao, H.; Wei, T. Chin. J. Org. Chem. 2019, 39, 1226. (in Chinese). |
[7] | ( 曲文娟, 房虎, 黄青, 张有明, 林奇, 姚虹, 魏太保, 有机化学, 2019, 39, 1226.) |
[8] | Li, Y.; Zhao, Y.; Jin, K.; Liu, J.; Zhou, X.; Yang, K. Chin. J. Org. Chem. 2019, 39, 1013. (in Chinese). |
[8] | ( 李英俊, 赵月, 靳焜, 刘季红, 周晓霞, 杨凯栋, 有机化学, 2019, 39, 1013.) |
[9] | Zhu, Y.; Wang, Z.; Yang, J.; Xu, X.; Wang, S. Chin. J. Org. Chem. 2019, 39, 427. (in Chinese). |
[9] | ( 朱阳明, 王忠龙, 杨剑, 徐徐, 王石发, 有机化学, 2019, 39, 427.) |
[10] | Li, Y.; Zhang, N.; Liu, J.; Jin, K.; Wang, S. Chin. J. Org. Chem. 2018, 38, 3026. (in Chinese). |
[10] | ( 李英俊, 张楠, 刘季红, 靳焜, 王思远, 有机化学, 2018, 38, 3026.) |
[11] | Gong, Z. L.; Zhong, Y. W. Inorg. Chem. 2016, 55, 10143. |
[12] | Jose, D. A.; Mishra, S.; Ghosh, A.; Shrivastav, A.; Mishra, S. K.; Das, A. Org. Lett. 2007, 9, 1979. |
[13] | Kim, H. N.; Moon, J. H.; Kim, S. K.; Kwon, J. Y.; Jang, Y. J.; Lee, J. Y.; Yoon, J. Y. J. Org. Chem. 2011, 76, 3805. |
[14] | Lopéz-Martínez, L. M.; García-Elías, J.; Ochoa-Terán, A.; Ortega, H. S.; Ochoa-Lara, K.; Montaño-Medina, C. U.; Yatsimirsky, A. K.; Ramírez, J. Z.; Labastida-Galván, V.; Ordoñez, M. Tetrahedron 2020, 76, 130815. |
[15] | Banerjee, M.; Ta, S.; Ghosh, M.; Ghosh, A.; Das, D. ACS Omega 2019, 4, 10877. |
[16] | Łukasik, N.; Chojnacki, J.; Luboch, E.; Okuniewski, A.; Wagner-Wysiecka, E. J. Photochem. Photobiol., 2020, 390, 112307. |
[17] | Naskar, K.; Bhanja, A. K.; Paul, S.; Pal, K.; Sinha, C. Cryst. Growth Des. 2020, 20, 6453. |
[18] | Sabater, P.; Zapata, F.; Bastida, A.; Caballero, A. Org. Biomol. Chem. 2020, 18, 3858. |
[19] | Ganjali, M. R.; Norouzi, P.; Alizadeh, T.; Adib, M. J. Braz. Chem. Soc. 2006, 17, 1217. |
[20] | Zhang, X. B.; Han, Z. X.; Fang, Z. H.; Shen, G. L.; Yu, R. Q. Anal. Chim. Acta 2006, 562, 210. |
[21] | Peng, H. Q.; Brooks, B. W.; Chan, R.; Chyan, O.; Point, T. W. L. Chemosphere 2002, 46, 1141. |
[22] | Wan, A. T.; Conyers, R. A.; Coombs, C. J.; Masterton, J. P. Clin. Chem. 1991, 37, 1683. |
[23] | Liu, C.; Huang, S. S.; Yao, H. R.; He, S.; Lu, Y.; Zhao, L. C.; Zeng, X. S. RSC Adv. 2014, 4, 16109. |
[24] | Yu, C.; Zhang, J.; Ding, M.; Chen, L. Anal. Methods 2012, 4, 342. |
[25] | Lou, T.; Chen, Z,; Wang, Y.; Chen, L. ACS Appl. Mater. Interfaces 2011, 3, 1568. |
[26] | Chen, L.; Zhao, Q.; Zhang, X. Y.; Tao, G. H. Chin. Chem. Lett. 2014, 25, 261. |
[27] | Ratte, H. T. Environ. Toxicol. Chem. 1999, 18, 89. |
[28] | Zhang, B.; Sun, J.; Bi, C.; Yin, G.; Pu, L.; Shi, Y.; Sheng, L. New J. Chem. 2011, 35, 849. |
[29] | Zhang, W.; Luo, Y.; Zhou, Y.; Liu, M.; Xu, W. T.; Bian, B.; Tao, Z.; Xiao, X. Dyes Pigm. 2020, 176, 108235. |
[30] | Wang, Y. J.; Liu, J. G.; Tan, H. Y.; Yan, J. W.; Zhang, L. RSC Adv. 2017, 7, 55567. |
[31] | Zhang, Y. W.; Ye, A. Y.; Yao, Y. W.; Yao, C. Sensors 2019, 19, 247. |
[32] | Kong, D. D.; Weng, T. Q.; He, W. X.; Liu, B.; Jin, S.; Hao, X.; Liu, S. H. J. Organomet. Chem. 2013, 727, 19. |
[33] | Liu, Q. X.; Zhao, X. J.; Hu, Z. L.; Zhao, Z. X.; Wang, H. Sci. Reports 2017, 7, 7534. |
[34] | Liu, K.; Zhao, X. J.; Liu, Q. X.; Huo, J. Z.; Li, Z. C.; Wang, X. X. Sens. Actuators, B 2017, 239, 883. |
[35] | Su, J. X.; Wang, X. T.; Chang, J.; Wu, G. Y.; Wang, H. M.; Yao, H.; Lin, Q.; Zhang, Y. M.; Wei, T. B. Spectrochim. Acta, Part A 2017, 182, 67. |
[36] | Qu, W. J.; Yan, G. T.; Ma, X. L.; Wei, T. B.; Lin, Q.; Yao, H.; Zhang, Y. M. Sens. Actuators, B 2017, 242, 849. |
[37] | Arumugaperumal, R.; Srinivasadesikan, V.; Raju, M. V. R.; Lin, M. C.; Shukla, T.; Singh, R.; Lin, H. C. ACS Appl. Mater. Interfaces 2015, 7, 26491. |
[38] | Suganyaa, S.; Velmathia, S.; Venkatesan, P.; Wu, S. P.; Boobalan, M. S. Inorg. Chem. Front. 2015, 2, 649. |
[39] | Liu, Q. C.; Liu, C.; Chang, L. F.; He, S.; Lu, Y.; Zeng, X. S. RSC Adv. 2014, 4, 14361. |
[40] | Wang, C. C.; Zhang, D.; Huang, X. Y.; Ding, P. G.; Wang, Z. J.; Zhao, Y. F.; Ye, Y. Sens. Actuators, B 2014, 198, 33. |
[41] | Prabhu, J.; Velmurugan, K.; Zhang, Q.; Radhakrishnan, S.; Tang, L.; Nandhakumar, R. J. Photochem. Photobiol., A 2017, 337, 6. |
[42] | Li, L. Q.; Gao, L. J. Spectrochim. Acta, Part A 2016, 152, 426. |
[43] | Ghosh, A.; Adhikari, S.; Ta, S.; Banik, A.; Dangar, T. K.; Mukherjee, S. K.; Matalobos, J. S.; Brandão, P.; Félix, V.; Das, D. Dalton Trans. 2016, 45, 19491. |
[44] | Velmurugan, K.; Suresh, S.; Santhoshkumar, S.; Saranyab, M.; Nandhakumara, R. Luminescence 2016, 31, 722. |
[45] | Wang, J. G.; Gu, X. G.; Zhang, P. F.; Huang, X. B.; Zheng, X. Y.; Chen, M.; Feng, H. T.; Ryan, T. K.; Jacky, W. Y.; Tang, B. Z. J. Am. Chem. Soc. 2017, 139, 16974. |
[46] | Liu, L.; Zhang, G. X.; Xiang, J. F.; Zhang, D. Q.; Zhu, D. B. Org. Lett. 2008, 10, 4581. |
[47] | Chen, Z.; Zhang, J.; Song, M.; Yin, J.; Yu, G. A.; Liu, S. H. Chem. Commun. 2015, 51, 326. |
[48] | Chen, Z.; Wu, D.; Han, X.; Liang, J.; Yin, J.; Yu, G. A.; Liu, S. H. Chem. Commun. 2014, 50, 11033. |
[49] | Jan, C. B. Han, V. H. Organometallics 2014, 33, 5845. |
[50] | Gu, X. X.; Zhu, X. C.; Wei, Y.; Wang, S. W.; Zhou, S. L.; Zhang, G. C.; Mu, X. L. Organometallics 2014, 33, 2372. |
[51] | Tomohisa, K.; Atsushi, K.; Kyosuke, N.; Kenichi, H. Biochem. Biophys. Res. Commun. 2010, 394, 200. |
[52] | Guan, X. L.; Zhang, D. H.; Meng, L.; Zhang, Y.; Jia, T. M.; Jin, Q. J.; Wei, Q. B.; Lu, D. D.; Ma, H. C. Ind. Eng. Chem. Res. 2017, 56, 680. |
/
〈 |
|
〉 |