Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring

doi:10.6023/cjoc201709046

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1126-1137.DOI: 10.6023/cjoc201709046 Previous Articles Next Articles

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含氮杂环多芳基咪唑衍生物的合成及其光物理性能

蔡柳, 吕柳, 王梦颖, 吴禹胜, 黃锦锋, 曾向潮

暨南大学化学与材料学院广州 510632

收稿日期:2017-09-29 修回日期:2017-12-21 发布日期:2018-01-18
通讯作者: 曾向潮,E-mail:xczeng@126.com E-mail:xczeng@126.com
基金资助:
国家大学生创新创业训练计划（No.201610559039）资助项目.

Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring

Cai Liu, Lü Liu, Wang Mengying, Wu Yusheng, Huang Jinfeng, Zeng Xiangchao

College of Chemistry and Materials Science, Jinan University, Guangzhou 510632

Received:2017-09-29 Revised:2017-12-21 Published:2018-01-18
Contact: 10.6023/cjoc201709046 E-mail:xczeng@126.com
Supported by:
Project supported by the National University Student Innovation Program of China (No. 201610559039).

1. Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring.PDF(2878KB)

Abstract

A series of novel imidazole derivatives containing indole or carbazole unit were efficiently synthesized via one-pot reaction of benzil/9, 10-phenanthraquinone, indole-3-carbaldehyde/carbazole-3-carbaldehyde and ammonium acetate utilizing glacial acetic acid as solvent and catalyst. The effects of selection and amount of solvents, molar ratio of the reagents, and temperature on the reactions have been surveyed. The photophysical properties of the synthesized products were also investigated, and two compounds possessing structural characteristics and pH-sensitive were selected as pH fluorescent probes. Furthermore, the fluorescence imaging of MCF-7 cells in different pH environments in the presence of the probe 2-(9-benzyl- 9H-carbazol-3-yl)-1H-4, 5-diphenylimidazole (2d) or 2-(9-benzyl-9H-carbazol-3-yl)-1H-phenanthro [9, 10-d]imidazole (4) was detected, and the results revealed that the two probes show promising potential to be used in detecting pH changes in living cells as pH fluorescent probes.

Key words: imidazole, indole, carbazole, bioimaging, pH fluorescent probe

Cite this article

Cai Liu, Lü Liu, Wang Mengying, Wu Yusheng, Huang Jinfeng, Zeng Xiangchao. Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring[J]. Chin. J. Org. Chem., 2018, 38(5): 1126-1137.

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[1] Golovina, V.-A.; Blaustein, M.-P. Science 1997, 275, 1643.
[2] Ishaque, A.; Al-Rubeai, M.-J. Immunol. Methods 1998, 221, 43.
[3] Anderson, R.-G.; Orci, W.-L. J. Cell Biol. 1988, 106, 539.
[4] Gillies, R.-J.; Raghunand, N.; Garcia-Martin, M.-L.; Gatenby, R.-A. IEEE Eng. Med. Biol. 2004, 23, 57.
[5] Izumi, H.; Torigoe, T.; Ishiguchi, H.; Uramoto, H.; Yoshida, Y.; Tanabe, M.; Ise, T.; Murakami, T.; Yoshida, T.; Nomoto, M.; Kohno, K. Cancer Treat. Rev. 2003, 29, 541.
[6] Vingtdeux, V.; Hamdane, M.; Begard, S.; Loyens, A.; Delacourte, A.; Beauvillain, J.-C.; Buee, L.; Marambaud, P.; Sergeant, N. Neurobiol. Dis. 2007, 25, 686.
[7] Fang, B.-Y.; Wang, D.-J.; Huang, M.-F.; Yu, G.-H.; Li, H. Int. J. Neurosci. 2010, 120, 591.
[8] Gottlieb, R.-A.; Giesing, H.-A.; Zhu, J.-Y.; Engler, R.-L.; Babior, B.-M. Proc. Natil. Acad. Sci. U. S. A. 1995, 92, 5965.
[9] Su, M.-H.; Liu, Y.; Ma, H.-M.; Ma, Q.-L.; Wang, Z.-H.; Yang, J.-L.; Wang, M.-X. Chem. Commun. 2001, 32, 960.
[10] Xu, Y.; Jiang, Z.; Xiao, Y.; Bi, F.-Z.; Miao, J.-Y.; Zhao, B.-X. Anal. Chim. Acta. 2014, 820, 146.
[11] Fan, L.; Gao, S.-Q.; Li, Z.-B.; Niu, W.-F.; Zhang, W.-J.; Shuang, S.-M.; Dong, C. Sens. Actuators, B 2015, 221, 1069.
[12] Niu, W.-F.; Fan, L.; Nan, M.; Li, Z.-B.; Lu, D.-T.; Wong, M.-S.; Shuang, S.-M.; Dong, C. Anal. Chem. 2015, 87, 2788.
[13] Chao, J. B.; Liu, Y.-H.; Sun, J.-Y.; Fan, L.; Zhang, Y.-B.; Tong, H.-H.; Li, Z.-Q. Sens. Actuators, B 2015, 221, 427.
[14] Zhang, X.; Jing, S.-Y.; Huang, S.-Y.; Zhou, X.-W.; Bai, J.-M.; Zhao, B.-X. Sens. Actuators, B 2015, 206, 663.
[15] Ma, Z.-Q.; Hu, L.; Zhong, C.; Zhang, H.; Liu, B.-F.; Liu, Z.-H. Sens. Actuators, B 2015, 219, 179.
[16] Chen, S.; Hong, Y.; Liu, Y.; Liu, J.; Leung, C. W. T.; Li, M.; Kwok, R. T. K.; Zhao, E.; Lam, J. W. Y.; Yu, Y.; Tang, B.-Z. J. Am. Chem. Soc. 2013, 135, 4926.
[17] Ge, F.-Y.; Yan, X.-L.; Yan, F.-Y.; Pan, H.-Y.; Chen, L.-G. J. Fluoresc. 2005, 15, 829.
[18] Shen, S.-L.; Chen, X.-P.; Zhang, X.-F.; Miao, J.-Y.; Zhao, B.-X. J. Mater. Chem. B 2015, 3, 919.
[19] Urano, Y.; Asanuma, D.; Hama, Y.; Koyama, Y.; Barrett, T.; Kamiya, M. Nat. Med. 2009, 15, 104.
[20] Myochin, T.; Kiyose, K.; Hanaoka, K.; Kojima, H.; Terai, T.; Nagano, T. J. Am. Chem. Soc. 2011, 133, 3401.
[21] Ai, H.-W.; Shaner, N.-C.; Cheng, Z.; Tsien, R.-Y.; Campbell, R.-E. Biochemistry 2007, 46, 5904.
[22] Nienhaus, K.; Nienhaus, G.-U.; Wiedenmann, J.; Nar, H.; Wolynes, P.-G. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 9156.
[23] Dong, J.; Solntsev, K.-M.; Poizat, O.; Tolbert, L.-M. J. Am. Chem. Soc. 2007, 129, 10084.
[24] Shaner, N.-C.; Steinbach, P.-A.; Tsien, R.-Y. Nat. Methods 2005, 2, 905.
[25] Shaner, N.-C.; Campbell, R.-E.; Steinbach, P.-A.; Giepmans, B.-N.; Palmer, A.-E.; Tsien, R.-Y. Nat. Biotechnol. 2004, 22, 1567.
[26] Zhang, R.; Li, J.-T.; Fu, C.-L.; Luo, X.-T. Mater. Rev. 2011, 25, 61(in Chinese). (张蓉, 李锦堂, 傅翠梨, 罗学涛, 材料导报, 2011, 25, 61.)
[27] Moon, H.; Hwang, J.; Kim, N.; Park, S.-Y. Macromolecules 2000, 33, 5116.
[28] Li, Q.-Q.; Li, Z.; Qin, J.-G. Prog. Chem. 2009, 21, 12(in Chinese). (李倩倩, 李振, 秦金贵, 化学进展, 2009, 21, 12.)
[29] Xiao, L.-W.; Peng, X.-X.; Zhou, Q.-X.; Kou, W.; Shi, Y.-R. Chin. J. Org. Chem. 2015, 35, 1204(in Chinese). (肖立伟, 彭晓霞, 周秋香, 寇伟, 时亚茹, 有机化学, 2015, 35, 1204.)
[30] Safari, J.; Khalili, S.-D.; Banitaba, S.-H. Synth. Commun. 2011, 41, 2359.
[31] Xiao, L.-W.; Gao, H.-J.; Kong, J.; Liu, G.-X.; Li, L.-L.; Duan, J.-D. Chin. J. Org. Chem. 2014, 34, 2511(in Chinese). (肖立伟, 高红杰, 孔洁, 刘光仙, 李玲玲, 段敬丹, 有机化学, 2014, 34, 2511.)
[32] Kannan, V.; Sreekumar, K. J. Mol. Catal. A:Chem. 2013, 376, 34.
[33] Li, B.-Z.; Gu, Q.; He, Y.-H.; Zhao, T.-Q.; Wang, S.-J.; Kang, J.; Zhang, Y.-M. C. R. Chim. 2012, 15, 784.
[34] Li, B.-Z.; Gu, Q.; Zhao, T.-Q.; He, Y.-H.; Tong, Y.-N.; Zhang, Y.-M. Chin. J. Org. Chem. 2012, 31, 1459(in Chinese). (李宝志, 顾强, 赵天琦, 贺元辉, 佟亚楠, 张玉敏, 有机化学, 2012, 31, 1459.)
[35] Tian, M.; Wang, C.; Wang, L.; Luo, K.; Zhao, A.; Guo, C. Luminescence 2013, 29, 540.
[36] Jezewski, A.; Hammann, T.; Cywinski, P.-J.; Gryko, D.-T. J. Phys. Chem. B 2015, 119, 2507.
[37] Ramezanalizadeh, H.; Manteghi, F. Monatsh. Chem. 2017, 148, 347.
[38] Al-Qawasmeh, R.-A.; Huesca, M.; Nedunuri, V.; Peralta, R.; Wright, J.; Lee, Y.; Young, A. Bioorg. Med. Chem. Lett. 2010, 20, 3518.
[39] Sharghi, H.; Aberi, M.; Doroodmand, M.-M. Mol. Diversity 2015, 19, 77.
[40] Teimouri, A.; Chermahini, A.-N. J. Mol. Catal. A:Chem. 2011, 346, 39.
[41] Park, S.; Kwon, J.-E.; Park, S.-Y. Phys. Chem. Chem. Phys. 2012, 14, 8878.
[42] Hranjec, M.; Horak, E.; Babic, D.; Plavljanin, S.; Srdovic, Z.; Steinberg, I.-M.; Vianello, R.; Perin, N. New J. Chem. 2017, 41, 358.
[43] Wu, Y.-C.; You, J.-Y.; Jiang, K.; Xie, J.-C.; Li, S.-L.; Cao, D.; Wang, Z.-Y. Dyes Pigm. 2017, 140, 47.
[44] Feng, H.; Thanhthuy, T.-T.; Chen, L.; Yuan, L.; Cai, Q. Chem. Eng. J. 2013, 215, 591.
[45] Hagberg, D.-P.; Edvinsson, T.; Marinado, T.; Boschloo, G.; Hagfeldt, A.; Sun, L. Chem. Commun. 2006, 21, 2245.
[46] Ishiyama, H.; Yoshizawa, K.; Kobayashi, J. Tetrahedron 2012, 68, 6186.
[47] Lin, Z.-Q.; Zeng, X.-C.; Meng, Y.-X. Chin. J. Org. Chem. 2015, 35, 490(in Chinese). (林志强, 曾向潮, 蒙玉霞, 有机化学, 2015, 35, 490.)
[48] Bian, L.; Zeng, X.-C.; He, R.; Luo, C.-L.; Lin, Z.-Q. Chin. J. Org. Chem. 2014, 34, 994(in Chinese). (卞垒, 曾向潮, 何如, 罗创龙, 林志强, 有机化学, 2014, 34, 994.)
[49] Zhang, W.-S.; Tang, B; Liu, X; Liu, Y.-Y.; Xu, K.-H.; Ma, J.-P.; Tong, L.-L.; Yang, G.-W. Analyst 2009, 134, 367.
[50] Zhu, Q.; Li, Z.; Mu, L.; Zeng, X.; Redshaw, C.; Wei, G. Spectrochim. Acta, Part A 2017, 188, 230.

含氮杂环多芳基咪唑衍生物的合成及其光物理性能

Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring

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