苯并氮杂环类荧光探针的设计、合成与应用研究进展

doi:10.6023/cjoc201904061

有机化学 ›› 2019, Vol. 39 ›› Issue (10): 2771-2785.DOI: 10.6023/cjoc201904061 上一篇下一篇

所属专题：荧光探针-生物传感合辑；有机超分子化学合辑

综述与进展

苯并氮杂环类荧光探针的设计、合成与应用研究进展

王能^a, ManiArulkumar^a, 陈孝云^b^*(), 王柏文^a, 陈思鸿^a, 姚辰^a, 汪朝阳^a^*()

^a 华南师范大学化学学院教育部环境理论化学重点实验室广州市生物医药分析化学重点实验室广州 510006
^b 江苏科技大学环境与化学工程学院镇江 212003

收稿日期:2019-04-25 修回日期:2019-05-14 发布日期:2019-06-03
通讯作者: 陈孝云,汪朝阳 E-mail:xiaoyun_chen12@163.com;wangzy@scnu.edu.cn
基金资助:
国家自然科学基金(21602085);广东省自然科学基金(2014A030313429);广州市科技计划科学研究专项(201607010251);江苏省自然科学基金(BK20160551);广东省科技计划(2017A010103016);华南师范大学大创计划资助项目(20191434)

Research Progress in Design, Synthesis and Application of Benzo Nitrogen-Containing Heterocyclic Fluorescent Probes

Wang Neng^a, Arulkumar Mani^a, Chen Xiaoyun^b^*(), Wang Bowen^a, Chen Sihong^a, Yao Chen^a, Wang Zhaoyang^a^*()

^a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006
^b School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003

Received:2019-04-25 Revised:2019-05-14 Published:2019-06-03
Contact: Chen Xiaoyun,Wang Zhaoyang E-mail:xiaoyun_chen12@163.com;wangzy@scnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(21602085);The Natural Science Foundation of Guangdong Province(2014A030313429);The Guangzhou Science and Technology Project Scientific Special(201607010251);The Natural Science Foundation of Jiangsu Province(BK20160551);The Guangdong Provincial Science and Technology Project(2017A010103016);The Undergraduates Innovation Project of South China Normal University(20191434)

文章分享

摘要/Abstract

苯并五元、六元氮杂环化合物具有刚性平面和大共轭结构, 能在多种有机溶剂、混合溶液中发出特征荧光, 且结构中的N、O、S杂原子可作为荧光探针的结合位点. 因此, 近年来苯并氮杂环化合物成为荧光探针领域研究焦点之一. 从所用原料、合成方式、分子结构、作用机理等角度, 重点介绍了苯并噁唑、苯并噻唑、苯并咪唑、吲哚及咔唑等苯并五元氮杂环, 喹啉、苯并吡嗪、吩嗪等苯并六元氮杂环, 以及两者共同构建的苯并多元氮杂环荧光探针的设计、合成, 并综述了它们对小分子、金属阳离子、阴离子、pH等多种分析物的检测应用.

关键词: 苯并五元氮杂环, 苯并六元氮杂环, 荧光探针, 设计与合成, 识别机理, 检测应用, 多功能化

Benzo five-/six-membered nitrogen-containing heterocyclic compound with a rigid plane and a large conjugate structure can emit characteristic fluorescence in a variety of organic solvents and mixed solutions, and N, O, S heteroatoms in the structure can serve as binding sites for fluorescent probes. Therefore, in recent years, benzo nitrogen-containing heterocyclic compounds are increasingly becoming one of the research focuses in the field of fluorescent probes. From the perspective of starting materials, synthesis methods, molecular structure, interaction mechanism, benzo five- / six-membered nitrogen-containing heterocyclic fluorescent probes containing the structure of benzoxazole, benzothiazole, benzimidazole, indole, carbazole, quinoline, benzopyrazine and phenazine are introduced with emphasis. And their detection application for a variety of analytes, such small molecules, metal cations, anions and pH are reviewed. In the future, it is worthy of further attention to the research on the integration of multiple heterocyclic functional structures into a multifunctional fluorescent probe by simple and green synthesis.

Key words: benzo five-membered nitrogen heterocycle, benzo six-membered nitrogen heterocycle, fluorescent probe, design and synthesis, recognition mechanism, detection application, multifunctionalization

引用此文

王能, ManiArulkumar, 陈孝云, 王柏文, 陈思鸿, 姚辰, 汪朝阳. 苯并氮杂环类荧光探针的设计、合成与应用研究进展[J]. 有机化学, 2019, 39(10): 2771-2785.

Wang Neng, Arulkumar Mani, Chen Xiaoyun, Wang Bowen, Chen Sihong, Yao Chen, Wang Zhaoyang. Research Progress in Design, Synthesis and Application of Benzo Nitrogen-Containing Heterocyclic Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2771-2785.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 24

图式1. 探针2的合成与作用机理

Scheme 1. Synthesis of probe 2 and its interaction mechanism

图式2. 探针3的合成

Scheme 2. Synthesis of probe 3

图式3. 探针6的合成与作用机理

Scheme 3. Synthesis of probe 6 and its interaction mechanism

图式4. 探针8的合成

Scheme 4. Synthesis of probe 8

图式5. 探针10的合成及其同分异构体11的结构

Scheme 5. Synthesis of probe 10 and structure of isomer 11

图式6. 探针12的合成与作用机理

Scheme 6. Synthesis of probe 12 and its interaction mechanism

图式7. 探针13的合成

Scheme 7. Synthesis of probe 13

图式8. 探针14的合成

Scheme 8. Synthesis of probe 14

图式9. 探针16的合成

Scheme 9. Synthesis of probe 16

图式10. 探针20的合成

Scheme 10. Synthesis of probe 20

图式11. 探针21的合成

Scheme 11. Synthesis of probe 21

图式12. 探针22的合成

Scheme 12. Synthesis of probe 22

图式13. 探针25的合成

Scheme 13. Synthesis of probe 25

图式14. 探针26的合成

Scheme 14. Synthesis of probe 26

图式15. 探针28的合成

Scheme 15. Synthesis of probe 28

图式16. 探针29的合成与作用机理

Scheme 16. Synthesis of probe 29 and its interaction mechanism

图式17. 探针30的合成与作用机理

Scheme 17. Synthesis of probe 30 and its interaction mechanism

图式18. 探针42~44的合成

Scheme 18. Synthesis of probes 42~44

图式19. 探针49的合成与作用机理

Scheme 19. Synthesis of probes 49 and its interaction mechanism

图式20. 探针52的合成与作用机理

Scheme 20. Synthesis of probe 52 and its interaction mechanism

图式21. 探针53的合成与作用机理

Scheme 21. Synthesis of probes 53 and its interaction mechanism

图式22. 探针55的合成和作用机理

Scheme 22. Synthesis of probe 55 and its interaction mechanism

图式23. 探针66的合成

Scheme 23. Synthesis of probe 66

图式24. 探针67的合成

Scheme 24. Synthesis of probes 67

参考文献 120

[1]	Malapati, P.; Krishna, V. S.; Nallangi, R.; Srilakshmi, R. R.; Sriram, D. Eur. J. Med. Chem. 2018, 145, 23. doi: 10.1016/j.ejmech.2017.12.088
[2]	Wei, P.-F.; Qi, M.-Z.; Wang, Z.-P.; Ding, S.-Y.; Yu, W.; Liu, Q.; Wang, L.-K.; Wang, H.-Z.; An, W.-K.; Wang, W. J. Am. Chem. Soc. 2018, 140, 4623. doi: 10.1021/jacs.8b00571
[3]	Garreffi, B. P.; Guo, M. L.; Tokranova, N.; Cady, N. C.; Castracane, J.; Levitsky, I.A. Sens. Actuators, B 2018, 276, 466. doi: 10.1016/j.snb.2018.07.115
[4]	Karman, M.; Verde-Sesto, E.; Weder, C. ACS Macro Lett. 2018, 7, 1028. doi: 10.1021/acsmacrolett.8b00520
[5]	Bing, Q. J.; Wang, L.; Li, D. L.; Wang, G. Spectrochim. Acta, Part A 2018, 202, 305. doi: 10.1016/j.saa.2018.05.045
[6]	Liu, K.; Guo, P.; Liu, L. J.; Shi, X.F. Sens. Actuators, B 2018, 250, 667. doi: 10.1016/j.snb.2017.04.111
[7]	Rostovtseva, I. A.; Chernyshev, A. V.; Tkachev, V. V.; Dorogan, I. V.; Voloshin, N. A.; Solov'eva, E. V.; Metelitsa, A. V.; Gaeva, E. B.; Aldoshin, S. M.; Minkin, V.I. J. Mol. Struct. 2017, 1145, 55. doi: 10.1016/j.molstruc.2017.05.089
[8]	Chen, S.; Wang, W. J.; Yan, M. M.; Tu, Q.; Chen, S.-W.; Li, T. B.; Yuan, M.-S.; Wang, J. Y . Sens. Actuators, B 2018, 255, 2086. doi: 10.1016/j.snb.2017.09.008
[9]	Lu, Z. X.; Liu, Y. M.; Lu, S. H.; Li, Y.; Liu, X. L.; Qin, Y.; Zheng, L.Y. RSC Adv. 2018, 8, 19701. doi: 10.1039/C8RA03591A
[10]	Mehta, P. K.; Oh, E.-T.; Park, H. J.; Lee, K.-H. Sens. Actuators, B 2018, 256, 393. doi: 10.1016/j.snb.2017.10.087
[11]	Chen, M. L.; Lü, X.; Liu, Y. L.; Zhao, Y.; Liu, J.; Wang, P.; Guo, W. Org. Biomol. Chem. 2011, 9, 2345. doi: 10.1039/c0ob00983k
[12]	Zhang, Y.; Wang, Y.-C.; Mei, J.-G.; Yang, N.-N.; Wang, W.-N.; Ai, S.-F.; Fang, Z.-Q. J. Chem. Res. 2016, 5, 280.
[13]	Chen, L.; Park, S. J.; Wu, D.; Kim, H. M.; Yoon, J. Dyes Pigm. 2018, 158, 526. doi: 10.1016/j.dyepig.2018.01.027
[14]	Shang, Y. T.; Zheng, S. W.; Tsakama, M.; Wang, M.; Chen, W.H. Tetrahedron Lett. 2018, 59, 4003. doi: 10.1016/j.tetlet.2018.09.057
[15]	Wang, J. F.; Li, Y. B.; Patel, N. G.; Zhang, G.; Zhou, D. M.; Pang, Y. Chem. Commun. 2014, 50, 12258. doi: 10.1039/C4CC04731A
[16]	Pang, Y.; Abeywickrama, C.S. Tetrahedron Lett. 2016, 57, 3518. doi: 10.1016/j.tetlet.2016.06.098
[17]	Abeywickrama, C. S.; Pang, Y. Tetrahedron Lett. 2017, 58, 1627. doi: 10.1016/j.tetlet.2017.03.030
[18]	Kwon, J. E.; Lee, S.; You, Y.; Baek, K. H.; Ohkubo, K.; Cho, J.; Fukuzumi, S.; Shin, I.; Park, S. Y.; Nam, W. Adv. Inorg. Chem. Radiochem. 2012, 51, 8760.
[19]	Sadhu, K. K.; Mizukami, S.; Yoshimura, A.; Kikuchi, K. Org. Biomol. Chem. 2013, 11, 563. doi: 10.1039/C2OB26630J
[20]	Ma, Q.-J.; Zhang, X.-B.; Zhao, X.-H.; Gong, Y.-J.; Tang, J.; Shen, G.-L.; Yu, R.-Q. Spectrochim. Acta, Part A 2017, 73, 687. doi: 10.1016/j.saa.2009.03.023
[21]	Yang, X. F.; Qin, X. J.; Li, Y. X.; Yan, M. Biosens. Bioelectron. 2018, 121, 62. doi: 10.1016/j.bios.2018.09.004
[22]	Esteves, C. I. C.; Ferreira, R. C. M.; Costa, S.P. G. Dyes Pigm. 2018, 151, 211. doi: 10.1016/j.dyepig.2017.12.040
[23]	Jiang, K.; Cao, L.; Hao, Z.-F.; Chen, M.-Y.; Cheng, J.-L.; Li, X.; Xiao, P.; Chen, L.; Wang, Z.-Y. Chin. J. Org. Chem. 2017, 37, 2221 (in Chinese). doi: 10.6023/cjoc201703041
	( 蒋凯, 曹梁, 郝志峰, 陈美燕, 程洁銮, 李晓, 肖萍, 陈亮, 汪朝阳, 有机化学, 2017, 37, 2221.) doi: 10.6023/cjoc201703041
[24]	Chen, L.; Wu, D.; Yoon, J. Sens. Actuators, B 2018, 259, 347. doi: 10.1016/j.snb.2017.12.073
[25]	Li, K.; Feng, Q.; Niu, G. L.; Zhang, W. J.; Li, Y. Y.; Kang, M. M.; Xu, K.; Hou, H. W.; Tang, B.Z. ACS Sens. 2018, 3, 920. doi: 10.1021/acssensors.7b00820
[26]	Kaur, I.; Kaur, P.; Singh, K. Sens. Actuators, B 2018, 257, 1083. doi: 10.1016/j.snb.2017.10.173
[27]	Niu, Q. F.; Lan, L. X.; Li, T. D.; Guo, Z. R.; Jiang, T.; Zhao, Z. Y.; Feng, Z. S.; Xi, J.Y. Sens. Actuators, B 2018, 276, 13. doi: 10.1016/j.snb.2018.08.066
[28]	Liu, Y.; Bi, A.Y.; Gao, Tang.; Cao, X. Z.; Gao, F.; Rong, P. F.; Wang, W.; Zeng, W. B. Talanta 2019, 194, 38. doi: 10.1016/j.talanta.2018.09.104
[29]	Hou, T. X.; Zhang, K.; Kang, X. X.; Guo, X. L.; Du, L. B.; Chen, X. F.; Yu, L.; Yue, J.; Ge, H. W.; Liu, Y.; Asiri, A. M.; Alamry, K. A.; Yu, H.; Wang, S. H. Talanta 2019, 196, 345. doi: 10.1016/j.talanta.2018.12.083
[30]	Nguyen, K. H.; Hao, Y. Q.; Zeng, K.; Fan, S. N.; Li, F.; Yuan, S. K.; Ding, X. J.; Xu, M. T.; Liu, Y.N. Spectrochim. Acta, Part A 2018, 199, 189. doi: 10.1016/j.saa.2018.03.055
[31]	Wang, S. J.; Li, J.; Gao, Y.; Guo, Y. Asian J. Org. Chem. 2018, 7, 563. doi: 10.1002/ajoc.v7.3
[32]	Shen, Y. M.; Zhang, X. Y.; Zhang, Y. Y.; Li, H. T.; Dai, L. C.; Peng, X. J.; Peng, Z.; Xie, Y.T. Anal. Chim. Acta 2018, 1014, 71. doi: 10.1016/j.aca.2018.01.046
[33]	Li, J.; Chen, Y. H.; Chen, T.T.; Qiang, J.; Zhang, Z. J.; Wei, T. W.; Zhang, W.; Wang, F.; Chen, X.Q. Sens. Actuators, B 2018, 268, 446. doi: 10.1016/j.snb.2018.04.130
[34]	Feng, G. F.; Luo, X. Y.; Lu, X.; Xie, S. Y.; Deng, L.; Kang, W. Y.; He, F.; Zhang, J. H.; Lei, C. Y.; Lin, B.; Huang, Y.; Nie, Z.; Yao, S.Z. Angew. Chem. 2019, 58, 6590. doi: 10.1002/anie.201901320
[35]	Wang, Y. T.; Wang, J. J.; Xian, Q. M. Talanta 2018, 190, 487. doi: 10.1016/j.talanta.2018.08.017
[36]	Zhang, J.; Wang, S.; Liu, C. H.; He, G. W.; Peng, T.Y. Chin. J. Chem. 2018, 36, 1179. doi: 10.1002/cjoc.v36.12
[37]	Diao, H. P.; Guo, L. X.; Liu, W.; Feng, L.H. Spectrochim. Acta, Part A 2018, 196, 274. doi: 10.1016/j.saa.2018.02.036
[38]	He, L.; Liu, X. J.; Zhang, Y.; Yang, L.; Fang, Q.; Geng, Y. N.; Chen, W. Q.; Song, X.Z. Sens. Actuators, B 2018, 276, 247. doi: 10.1016/j.snb.2018.08.119
[39]	Hu, Y.; Joung, J. F.; Jeong, J. E.; Jeong, Y.; Woo, H. Y.; She, Y. B.; Park, S.; Yoon, J. Sens. Actuators, B 2019, 280, 298. doi: 10.1016/j.snb.2018.10.043
[40]	Wu, Y.-C.; You, J.-Y.; Guan, L.-T.; Shi, J.; Cao, L.; Wang, Z.-Y. Chin. J. Org. Chem. 2015, 35, 2465 (in Chinese). doi: 10.6023/cjoc201507022
	( 吴彦城, 尤嘉宜, 关丽涛, 石杰, 曹梁, 汪朝阳, 有机化学, 2015, 35, 2465.) doi: 10.6023/cjoc201507022
[41]	Li, G.; Zhang, D. B.; Liu, G.; Pu, S.Z. Tetrahedron Lett. 2016, 57, 5205. doi: 10.1016/j.tetlet.2016.10.027
[42]	Liu, L. L.; Dan, F. J.; Liu, W. J.; Lu, X.; Han, Y. L.; Xiao, S. Z.; Lan, H.C. Sens. Actuators, B 2017, 247, 445. doi: 10.1016/j.snb.2017.03.069
[43]	Mashraqui, S. H.; Chandiramani, M.; Ghorpade, S.; Upathayay, J.; Mestri, R.; Chilekar, A. J. Inclusion Phenom. Macrocyclic Chem. 2016, 84, 129. doi: 10.1007/s10847-015-0590-z
[44]	Wu, Y.-C.; Jiang, K.; Luo, S.-H.; Cao, L.; Wu, H.-Q.; Wang, Z.-Y. Spectrochim. Acta, Part A 2019, 206, 632. doi: 10.1016/j.saa.2018.05.069
[45]	Iniya, M.; Jeyanthi, D.; Krishnaveni, K.; Chellappa, D. J. Lumin. 2015, 157, 383. doi: 10.1016/j.jlumin.2014.09.018
[46]	Li, Z. S.; Li, L. J.; Sun, T. T.; Liu, L. M.; Xie, Z.G. Dyes Pigm. 2016, 128, 165. doi: 10.1016/j.dyepig.2016.01.029
[47]	Zhu, W. J.; Fang, M.; Zhang, Q.; Xu, Y.; Wu, Z. Y.; Li, C. J. Chin. Chem. Soc. 2018, 65, 597. doi: 10.1002/jccs.2018.65.issue-5
[48]	Zhao, M. L.; Deng, Z. F.; Tang, J.; Zhou, X. F.; Chen, Z.; Li, X. T.; Yang, L. T.; Ma, L. J. Analyst 2016, 141, 2308. doi: 10.1039/C5AN02565F
[49]	Bing, Q. J.; Wang, L.; Li, D. L.; Wang, G. Spectrochim. Acta, Part A 2018, 202, 305. doi: 10.1016/j.saa.2018.05.045
[50]	Lu, Z. X.; Liu, Y. M.; Lu, S. H.; Li, Y.; Liu, X. L.; Qin, Y.; Zheng, L.Y. RSC Adv. 2018, 8, 19701. doi: 10.1039/C8RA03591A
[51]	Krishnaveni, K.; Iniya, M.; Jeyanthi, D.; Siva, A.; Chellappa, D. Spectrochim. Acta, Part A 2018, 205, 557. doi: 10.1016/j.saa.2018.07.075
[52]	Sen Gupta, A.; Garg, A.; Paul, K.; Luxami, V. J. Lumin. 2016, 173, 16.
[53]	Ge, Y. Q.; Liu, A. K.; Ji, R. X.; Shen, S. L.; Cao, X.Q. Sens. Actuators, B 2017, 251, 410. doi: 10.1016/j.snb.2017.05.097
[54]	Goswami, S.; Maity, S.; Maity, A. C.; Maity, A. K.; Das, A. K.; Saha, P. RSC Adv. 2014, 4, 6300. doi: 10.1039/c3ra46280c
[55]	Chen, C. J.; Liu, H. Y.; Zhang, B.; Wang, Y. W.; Cai, K.; Tan, Y.; Gao, C. M.; Liu, H. X.; Tan, C. Y.; Jiang, Y. Y. Tetrahedron 2016, 72, 3980. doi: 10.1016/j.tet.2016.05.020
[56]	Ta, S.; Das, S.; Ghosh, M.; Banerjee, M.; Hira, S. K.; Manna, P. P.; Das, D. Spectrochim. Acta, Part A 2019, 209, 170. doi: 10.1016/j.saa.2018.10.006
[57]	Paul, A.; Anbu, S.; Sharma, G.; Kuznetsov, M. L.; da Silva, M. F. C. G.; Koch, B.; Pombeiro, A.J. L. Dalton Trans. 2015, 44, 16953. doi: 10.1039/C5DT02662H
[58]	Dhaka, G.; Kaur, N.; Singh, J. Inorg. Chem. Commun. 2016, 72, 57. doi: 10.1016/j.inoche.2016.08.008
[59]	Gao, Y. L.; Zhang, C.; Peng, S. W.; Chen, H.Y. Sens. Actuators, B 2017, 238, 455. doi: 10.1016/j.snb.2016.07.076
[60]	Bieleszova, K.; Parizkova, B.; Kubes, M.; Husickova, A.; Kubala, M.; Ma, Q.; Sedlarova, M.; Robert, S.; Dolezal, K.; Strnad, M.; Novak, O.; Zukauskaite, A. New Biotechnol. 2019, 48, 44. doi: 10.1016/j.nbt.2018.06.003
[61]	More, G. V.; Bhanage, B.M. Catal. Sci. Technol. 2015, 5, 1514. doi: 10.1039/C4CY01456A
[62]	Samanta, S.; Ray, T.; Haque, F.; Das, G. J. Lumin. 2016, 171, 13. doi: 10.1016/j.jlumin.2015.10.043
[63]	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. doi: 10.1016/j.snb.2015.07.076
[64]	Joshi, S.; Kumari, S.; Sarmah, A.; Pant, D. D.; Sakhuja, R. J. Mol. Liq. 2017, 248, 668. doi: 10.1016/j.molliq.2017.10.081
[65]	Lin, W. C.; Hu, J. W.; Chen, K.Y. Anal. Chim. Acta 2015, 893, 91. doi: 10.1016/j.aca.2015.08.044
[66]	Shan, Y. Y.; Wu, Q. Q.; Sun, N.; Sun, Y. H.; Cao, D. X.; Liu, Z. Q.; Guan, R. F.; Xu, Y. X.; Yu, X.Y. Mater. Chem. Phys. 2017, 186, 295 doi: 10.1016/j.matchemphys.2016.10.056
[67]	Tang, Y.; Jiang, G.F. Tetrahedron Lett. 2017, 58, 2846. doi: 10.1016/j.tetlet.2017.06.024
[68]	Tumay, S. O.; Okutan, E.; Sengul, I. F.; Ozcan, E.; Kandemir, H.; Doruk, T.; Cetin, M.; Cosut, B. Polyhedron 2016, 117, 161. doi: 10.1016/j.poly.2016.05.056
[69]	Xu, T.; Duan, H. D.; Wang, X. J.; Meng, X.; Bu, J. Spectrochim. Acta, Part A 2015, 138, 603. doi: 10.1016/j.saa.2014.11.098
[70]	Jeyanthi, D.; Iniya, M.; Krishnaveni, K.; Chellappa, D. Spectrochim. Acta, Part A 2015, 136, 1269. doi: 10.1016/j.saa.2014.10.013
[71]	Lv, Z. X.; Sun, Z. W.; Song, C. H.; Lu, S. M.; Chen, G.; You, J. M. Talanta 2016, 161, 228. doi: 10.1016/j.talanta.2016.08.040
[72]	Huang, Y. L.; Zhou, Q.; Feng, Y.; Zhang, W.; Fang, G. S.; Fang, M.; Chen, M.; Xu, C. Z.; Meng, X.M. Chem. Commun. 2018, 54, 10495. doi: 10.1039/C8CC05594G
[73]	Ning, P.; Hou, L. L.; Feng, Y.; Xu, G. Y.; Bai, Y. Y.; Yu, H. Z.; Meng, X.M. Chem. Commun. 2019, 55, 1782. doi: 10.1039/C8CC09517E
[74]	Feng, Y.; Li, S. Q.; Li, D. X.; Wang, Q.; Ning, P.; Chen, M.; Tian, X. H.; Wang, X. Sens. Actuators, B 2018, 254, 282. doi: 10.1016/j.snb.2017.07.019
[75]	Shi, G.; Shahid, M. A.; Yousuf, M.; Mahmood, F.; Rasheed, L.; Bielawski, C. W.; Kim, K. S . Chem. Commun. 2019, 55, 1470. doi: 10.1039/C8CC08958B
[76]	Lin, D. Y.; Fei, X. N.; Li, R.; Gu, Y. C.; Tang, Y. L.; Zhou, J. G.; Zhang, B. L . J. Fluoresc. Chem. Commun. 2016, 26, 1511. doi: 10.1007/s10895-016-1851-y
[77]	Patra, L.; Aich, K.; Gharami, S.; Mondal, T.K. J. Lumin. 2018, 201, 419. doi: 10.1016/j.jlumin.2018.05.020
[78]	Bi, K. Y.; Tan, R.; Hao, R. T.; Miao, L. X.; He, Y. Q.; Wu, X. H.; Zhang, J. F.; Xu, R. Chin. Chem. Lett. 2019, 30, 545. doi: 10.1016/j.cclet.2018.11.020
[79]	Kandemir, H.; Kocak, A.; Tumay, S. O.; Cosut, B.; Zorlu, Y.; Sengul, I.F. Turk. J. Chem. 2018, 42, 221.
[80]	Sanchez, G.; Espinosa, A.; Curiel, D.; Tarraga, A.; Molina, P. J. Org. Chem. 2013, 78, 9725. doi: 10.1021/jo401430d
[81]	Yang, L. L.; Wang, J. P.; Yang, L.; Zhang, C.; Zhang, R. L.; Zhang, Z. P.; Liu, B. H.; Jiang, C.L. RSC Adv. 2016, 6, 56384. doi: 10.1039/C6RA10293J
[82]	Wang, W. D.; Hu, Y.; Hu, S.L. Inorg. Chim. Acta 2018, 477, 206. doi: 10.1016/j.ica.2018.03.033
[83]	Zhou, F. F.; Wang, H. Q.; Liu, P. Y.; Hu, Q. H.; Wang, Y. Y.; Liu, C.; Hu, J.K. Spectrochim. Acta, Part A 2018, 190, 104. doi: 10.1016/j.saa.2017.09.007
[84]	Liu, X. J.; Su, Y. A.; Tian, H. H.; Yang, L.; Zhang, H. Y.; Song, X. Z.; Foley, J.W. Anal. Chem. 2017, 89, 7038. doi: 10.1021/acs.analchem.7b00754
[85]	Wu, G. F.; Li, M. X.; Zhu, J. J.; Lai, K. W. C.; Tong, Q. X.; Lu, F. RSC Adv. 2016, 6, 100696. doi: 10.1039/C6RA19734E
[86]	Gupta, R. C.; Razi, S. S.; Ali, R.; Dwivedi, S. K.; Srivastava, P.; Singh, P.; Koch, B.; Mishra, H.; Misra, A. Sens. Actuators, B 2017, 251, 729. doi: 10.1016/j.snb.2017.04.096
[87]	Wang, L. F.; Qian, Y. J. Photochem. Photobiol., A 2019, 372, 122. doi: 10.1016/j.jphotochem.2018.12.013
[88]	Dai, Y. P.; Yao, K.; Fu, J. X.; Xue, K.; Yang, L.; Xu, K.X. Sens. Actuators, B 2017, 251, 877. doi: 10.1016/j.snb.2017.05.103
[89]	Obali, A. Y.; Yilmaz, M. S.; Ucan, H.I. J. Mol. Struct. 2017, 1145, 192. doi: 10.1016/j.molstruc.2017.05.047
[90]	Liu, H. Y.; Tan, Y.; Dai, Q. Z.; Liang, H. D.; Song, J.; Qu, J. L.; Wong, W.Y. Dyes Pigm. 2018, 158.
[91]	Luo, Z. L.; Yin, K.; Yu, Z.; Chen, M. X.; Li, Y.; Ren, J. Spectrochim. Acta, Part A 2016, 169, 38. doi: 10.1016/j.saa.2016.06.022
[92]	Li, B.; Tian, J. F.; Zhang, D.; Tian, F. L. Luminescence 2017, 32, 1567. doi: 10.1002/bio.v32.8
[93]	Marimuthu, P.; Ramu, A. Sens. Actuators, B 2018, 266, 384. doi: 10.1016/j.snb.2018.03.158
[94]	Murugan, A. S.; Vidhyalakshmi, N.; Ramesh, U.; Annaraj, J. Sens. Actuators, B 2018, 274, 22. doi: 10.1016/j.snb.2018.07.104
[95]	Adhikari, S.; Mandal, S.; Ghosh, A.; Guria, S.; Pal, A.; Adhikary, A.; Das, D. J. Photochem. Photobiol., A 2018, 360, 26. doi: 10.1016/j.jphotochem.2018.04.005
[96]	Han, J.; Tang, X.; Wang, Y.; Liu, R. J.; Wang, L.; Ni, L . Spectrochim. Acta, Part A 2018, 205, 597. doi: 10.1016/j.saa.2018.07.081
[97]	Manikandan, I.; Chang, C. H.; Chen, C. L.; Sathish, V.; Li, W. S.; Malathi, M. Spectrochim. Acta, Part A 2017, 182, 58. doi: 10.1016/j.saa.2017.03.055
[98]	Deng, Y.; Niu, W. P.; Wang, Z. J.; Feng, L.H. Sens. Actuators, B 2017, 238, 613. doi: 10.1016/j.snb.2016.07.130
[99]	Zhao, Q.; Liu, X. M.; Li, H. R.; Zhang, Y. H.; Bu, X.H. Dalton Trans. 2016, 45, 10836. doi: 10.1039/C6DT01161F
[100]	Cui, M. M.; Li, W. T.; Wang, L. Y.; Gong, L. S.; Tang, H.; Cao, D.R. J. Mater. Chem. C 2019, 7, 3779. doi: 10.1039/C8TC05360J
[101]	Weldekirstos, H. D.; Kuo, M. C.; Li, S. R.; Su, W. L.; Desta, M. A.; Wu, W. T.; Kuo, C. H.; Sun, S.S. Dyes Pigm. 2019, 163, 761. doi: 10.1016/j.dyepig.2018.12.042
[102]	Chen, H. Y.; Zhou, Z. L.; Lu, Q. J.; Wu, C. Y.; Liu, M. L.; Zhang, Y. Y.; Yao, S.Z. Anal. Chim. Acta 2019, 1051, 160. doi: 10.1016/j.aca.2018.11.027
[103]	More, Y. W.; Padghan, S. D.; Bhosale, R. S.; Pawar, R. P.; Puyad, A. L.; Bhosale, S. V.; Bhosale, S. V. Sensors 2018, 18, 3433. doi: 10.3390/s18103433
[104]	Mahanta, S. P.; Panda, P.K. J. Chem. Sci. 2017, 129, 647. doi: 10.1007/s12039-017-1272-8
[105]	Han, H.; Liu, Y. R.; Dong, C.; Han, X.E. J. Lumin. 2017, 183, 513. doi: 10.1016/j.jlumin.2016.11.065
[106]	Ishtiaq, M.; Munir, I.; Al-Rashida, M.; Maria.; Ayub, K.; Iqbal, J.; Ludwig, R.; Khan, K. M.; Ali, S. A.; Hameed, A. RSC Adv. 2016, 6, 64009. doi: 10.1039/C6RA14134J
[107]	Feng, L.; Shi, W.; Ma, J. C.; Chen, Y. B.; Kui, F.; Hui, Y. H.; Xie, Z.F. Sens. Actuators, B 2016, 237, 563. doi: 10.1016/j.snb.2016.06.129
[108]	Che, C. L.; Chen, X. Z.; Wang, H. M.; Li, J. Q.; Xiao, Y. M.; Fu, B.; Qin, Z.H. New J. Chem. 2018, 42, 12773. doi: 10.1039/C8NJ01614C
[109]	Shi, W.; Lei, Y. L.; Hui, Y. H.; Mi, H. Y.; Ma, F. D.; Tian, Y.; Xie, Z.F. New J. Chem. 2014, 38, 4730. doi: 10.1039/C4NJ00492B
[110]	Cui, W.; Wang, L. Y.; Xiang, G.; Zhou, L. X.; An, X. N.; Cao, D.R. Sens. Actuators, B 2015, 207, 281. doi: 10.1016/j.snb.2014.10.072
[111]	Zhu, L. M.; Yang, J.; Wang, Q. S.; Zeng, L.T. J. Lumin. 2014, 148, 161. doi: 10.1016/j.jlumin.2013.12.019
[112]	Zhang, H. L.; Wei, T. B.; Li, W. T.; Qu, W. J.; Leng, Y. L.; Zhang, J. H.; Lin, Q.; Zhang, Y. M.; Yao, H. Spectrochim. Acta, Part A 2017, 175, 117. doi: 10.1016/j.saa.2016.12.022
[113]	de Moliner, F.; King, A.; Dias, G. G.; de Lima, G. F.; de Simone, C. A.; da Silva, E. N.; Vendrell, M. Front. Chem. 2018, 6, 339. doi: 10.3389/fchem.2018.00339
[114]	Shi, B. B.; Zhang, Y. M.; Wei, T. B.; Lin, Q.; Yao, H.; Zhang, P.; You, X.M. Sens. Actuators, B 2014, 190, 555. doi: 10.1016/j.snb.2013.09.043
[115]	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. doi: 10.1016/j.snb.2016.08.016
[116]	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. doi: 10.1016/j.snb.2015.02.077
[117]	Aggarwal, K.; Khurana, J.M. J. Photochem. Photobiol., A 2015, 307, 23.
[118]	Aggarwal, K.; Khurana, J.M. J. Lumin. 2015, 167, 146. doi: 10.1016/j.jlumin.2015.06.027
[119]	Jiang, K.; Luo, S.-H.; Pang, C.-M.; Wang, B.-W.; Wu, H.-Q.; Wang, Z.-Y. Dyes Pigm. 2019, 162, 367. doi: 10.1016/j.dyepig.2018.10.041
[120]	Jiang, K.; Chen, S.-H.; Luo, S.-H.; Pang, C.-M.; Wu, X.-Y.; Wang, Z.-Y. Dyes Pigm. 2019, 167, 164. doi: 10.1016/j.dyepig.2019.04.023

苯并氮杂环类荧光探针的设计、合成与应用研究进展

Research Progress in Design, Synthesis and Application of Benzo Nitrogen-Containing Heterocyclic Fluorescent Probes

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 24

参考文献 120

相关文章 15

编辑推荐

相关统计

本文评价

[1]	张莹珍, 江丹丹, 李娟华, 王菁菁, 刘昆明, 刘晋彪. 高选择性硒代半胱氨酸荧光探针的构建策略及成像[J]. 有机化学, 2024, 44(1): 41-53.
[2]	杨维清, 葛宴兵, 陈元元, 刘萍, 付海燕, 马梦林. 1,8-萘酰亚胺衍生物的设计、合成及其对半胱氨酸的识别研究[J]. 有机化学, 2024, 44(1): 180-194.
[3]	李焕清, 陈兆华, 陈祖佳, 邱琪雯, 张又才, 陈思鸿, 汪朝阳. 基于有机小分子的汞离子荧光探针研究进展[J]. 有机化学, 2023, 43(9): 3067-3077.
[4]	丁炳辉, 韩少辉, 熊海青, 王本花, 左伯军, 宋相志. 高选择性比率型荧光探针用于急性肺损伤中次氯酸的检测[J]. 有机化学, 2023, 43(8): 2878-2884.
[5]	刘飞冉, 敬静, 张小玲. 细胞器靶向型半胱氨酸荧光探针研究进展[J]. 有机化学, 2023, 43(6): 2053-2067.
[6]	李宜芳, 王耀, 牛华伟, 陈秀金, 李兆周, 王永国. 线粒体靶向的二氧化硫荧光探针研究进展[J]. 有机化学, 2023, 43(6): 1952-1962.
[7]	刘甜甜, 张鸿鹏, 焦晓梦, 白银娟. 多信号同时检测生物硫醇荧光探针的研究进展[J]. 有机化学, 2023, 43(6): 2081-2095.
[8]	陈志华, 胡艳, 马丽丽, 张子怡, 刘传祥. 基于氢化吡啶辅助氨基氧化策略的次氯酸根荧光探针的设计、合成及其性能研究[J]. 有机化学, 2023, 43(2): 718-724.
[9]	唐宏伟, 王超, 钟克利, 侯淑华, 汤立军, 边延江. 一种裸眼和荧光双通道快速检测Hg²⁺的探针及其多种应用[J]. 有机化学, 2023, 43(2): 712-717.
[10]	周五, 彭敏, 梁庆祥, 吴爱斌, 舒文明, 余维初. 高选择和高灵敏检测溶液和气相中硫化氢的新型萘酰亚胺类开启型荧光探针[J]. 有机化学, 2023, 43(12): 4277-4283.
[11]	刘梦, 黄延茹, 孙小飞, 汤立军. 一种基于“聚集诱导发光+激发态分子内质子转移”机制的苯并噻唑衍生物荧光探针及其对次氯酸根的识别[J]. 有机化学, 2023, 43(1): 345-351.
[12]	李阳阳, 孙小飞, 胡晓玲, 任源远, 钟克利, 燕小梅, 汤立军. 三苯胺衍生物的合成及其基于聚集诱导发光(AIE)机理对汞离子“OFF-ON”荧光识别[J]. 有机化学, 2023, 43(1): 320-325.
[13]	张继东, 颜婉琳, 胡文强, 郭典, 张大龙, 权校昕, 卜贤盼, 陈思宇. 一种具有聚集诱导发光性能的Zn²⁺荧光探针的设计合成[J]. 有机化学, 2023, 43(1): 326-331.
[14]	马延慧, 武宇乾, 王晓旭, 高贵, 周欣. 基于1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO)的近红外荧光探针研究进展[J]. 有机化学, 2023, 43(1): 94-111.
[15]	杨雅馨, 陈琳, 胡晓玲, 钟克利, 李世迪, 燕小梅, 张璟琳, 汤立军. 一种点亮型硫化氢荧光探针的合成及其在红酒和细胞中的应用[J]. 有机化学, 2023, 43(1): 308-312.