Citation: Jun Zhang, Mengyao She, Lang Liu, Mengdi Liu, Zhaohui Wang, Hua Liu, Wei Sun, Xiaogang Liu, Ping Liu, Shengyong Zhang, Jianli Li. Construction and regulation of imidazo[1, 5-a]pyridines with AIE characteristics via iodine mediated Csp²−H or Csp−H amination[J]. Chinese Chemical Letters, ;2021, 32(10): 3083-3086. doi: 10.1016/j.cclet.2021.05.018 shu

Construction and regulation of imidazo[1, 5-a]pyridines with AIE characteristics via iodine mediated Csp²−H or Csp−H amination

Jun Zhang ^{a, 1} ,
Mengyao She ^{a, b, 1} ,
Lang Liu ^a ,
Mengdi Liu ^a ,
Zhaohui Wang ^a ,
Hua Liu ^a ,
Wei Sun ^a ,
Xiaogang Liu ^c ,
Ping Liu ^a ,
Shengyong Zhang ^a ,
Jianli Li ^{a, *,}

a.
Ministry of Education Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China
b.
Lab of Tissue Engineering, Provincial Key Laboratory of Biotechnology of Shaanxi, Ministry of Education Key Laboratory of Resource Biology and Modern Biotechnology, The College of Life Sciences, Faculty of Life and Health Science, Northwest University, Xi'an 710127, China
c.
Fluorescence Research Group, Singapore University of Technology and Design, Singapore 487372, Singapore

lijianli@nwu.edu.cn

Received Date: 21 February 2021
Revised Date: 7 May 2021
Accepted Date: 13 May 2021
Available Online: 24 May 2021

Figures(5)

The widespread applications of aggregation-induced emission luminogens (AIEgens) inspire the creation of AIEgens with novel structures and functionalities. In this work, we focused on the direct and efficient synthesis of a new type of AIEgens, imidazo[1, 5-a]pyridicne derivatives, via iodine mediated cascade oxidative Csp²–H or Csp–H amination route from phenylacetylene or styrenes under mild conditions. The resulted compounds showed excellent AIE characteristics with tunable maximum emissions, attractive bioimaging performance, and potential anti-inflammatory activity, which exert broad application prospects in material, biology, medicine, and other relevant areas.
- Aggregation-induced emission (AIE),
- Imidazo[1, 5-a]pyridicnes,
- Iodine,
- Bioimaging,
- Anti-inflammatory
1. [1]
  J. Luo, Z. Xie, J.W.Y. Lam, et al., Chem. Commun. (2001) 1740–1741 doi: 10.1039/b105159h
2. [2]
  Q. Gao, L.H. Xiong, T. Han, et al., J. Am. Chem. Soc. 141 (2019) 14712–14719 doi: 10.1021/jacs.9b06493
3. [3]
  W. Chen, F. Song, Chin. Chem. Lett. 30 (2019) 1717–1730 doi: 10.1016/j.cclet.2019.08.032
4. [4]
  C. Wang, Z. Liu, M. Li, et al., Chem. Sci. 8 (2017) 3750–3758 doi: 10.1039/C6SC05648B
5. [5]
  J.D. Zhang, Z. Yan, S. Wang, et al., Dyes Pigm. 150 (2018) 112–120 doi: 10.4103/wjtcm.wjtcm_14_18
6. [6]
  D. Ding, G. Zhang, B.Z. Tang, L. Zheng, B. Situ, Patent, CN111239391 (A), 2020.
7. [7]
  D.D. La, S.V. Bhosale, L.A. Jones, S.V. Bhosale, ACS Appl. Mater. Interfaces 10 (2018) 12189–12216 doi: 10.1021/acsami.7b12320
8. [8]
  J. Mei, N.L.C. Leung, R.T.K. Kwok, J.W.Y. Lam, B.Z. Tang, Chem. Rev. 115 (2015) 11718–11940 doi: 10.1021/acs.chemrev.5b00263
9. [9]
  Y. Zhang, Y. Wang, J. Wang, X.J. Liang, Mater. Horiz. 5 (2018) 799–812 doi: 10.5325/complitstudies.55.4.0799
10. [10]
  P. Shen, Z. Zhuang, Z. Zhao, B.Z. Tang, J. Mater. Chem. C6 (2018) 11835–11852 doi: 10.1039/c8tc02956c
11. [11]
  Y. Yu, J. Chen, S. Tan, et al., J. Mater. Chem. C9 (2021) 888–893 doi: 10.1039/d0tc04830e
12. [12]
  L. Zhang, Y.F. Wang, M. Li, Q.Y. Gao, C.F. Chen, Chin. Chem. Lett. 32 (2021) 740–744 doi: 10.1016/j.cclet.2020.07.041
13. [13]
  W. Chi, J. Chen, W. Liu, et al., J. Am. Chem. Soc. 142 (2020) 6777–6785 doi: 10.1021/jacs.0c01473
14. [14]
  S. Chen, H. Li, P. Hou, Anal. Chim. Acta 993 (2017) 63–70 doi: 10.1016/j.aca.2017.09.016
15. [15]
  Y. Ge, R. Ji, S. Shen, X. Cao, F. Li, Sens. Actuators B 245 (2017) 875–881 doi: 10.1016/j.snb.2017.01.169
16. [16]
  S.L. Shen, X.Q. Huang, X.H. Lin, X.Q. Cao, Anal. Chim. Acta 1052 (2019) 124–130 doi: 10.1016/j.aca.2018.11.030
17. [17]
  H. Sheng, Y. Hu, Y. Zhou, et al., Dyes Pigments. 160 (2019) 48–57 doi: 10.1016/j.dyepig.2018.07.036
18. [18]
  K. Tajima, N. Fukui, H. Shinokubo, Org. Lett. 21 (2019) 9516–9520 doi: 10.1021/acs.orglett.9b03699
19. [19]
  K. Sun, X.L. Chen, S.J. Li, et al., J. Org. Chem. 83 (2018) 14419–14430 doi: 10.1021/acs.joc.8b02175
20. [20]
  M. Liu, S. Ma, M.Y. She, et al., Chin. Chem. Lett. 30 (2019) 1815–1824 doi: 10.1016/j.cclet.2019.08.028
21. [21]
  F. Shibahara, R. Sugiura, E. Yamaguchi, A. Kitagawa, T. Murai, J. Org. Chem. 74 (2009) 3566–3568 doi: 10.1021/jo900415y
22. [22]
  Z. Xie, J. Peng, Q. Zhu, Org. Chem. Front. 3 (2016) 82–86 doi: 10.1039/C5QO00313J
23. [23]
  S. Chuprakov, F.W. Hwang, V. Gevorgyan, Angew. Chem. Int. Ed. 46 (2007) 4757–4759 doi: 10.1002/anie.200700804
24. [24]
  A. Joshi, D.C. Mohan, S. Adimurthy, J. Org. Chem. 81 (2016) 9461–9469 doi: 10.1021/acs.joc.6b01742
25. [25]
  A. Joshi, D.C. Mohan, S. Adimurthy, Org. Lett. 18 (2016) 464–467 doi: 10.1021/acs.orglett.5b03509
26. [26]
  H. Wang, W. Xu, Z. Wang, L. Yu, K. Xu, J. Org. Chem. 80 (2015) 2431–2435 doi: 10.1021/jo5027723
27. [27]
  M. Li, Y. Xie, Y. Ye, et al., Org. Lett. 16 (2014) 6232–6235 doi: 10.1021/ol503165b
28. [28]
  C.T. Feng, H.J. Wei, J. Li, Y. Peng, K. Xu, Adv. Synth. Catal. 360 (2018) 4726–4730 doi: 10.1002/adsc.201801060
29. [29]
  P. Qian, Z. Zhou, K. Hu, et al., Org. Lett. 21 (2019) 6403–6407 doi: 10.1021/acs.orglett.9b02317
30. [30]
  H. Wang, W. Xu, L. Xin, et al., J. Org. Chem. 81 (2016) 3681–3687 doi: 10.1021/acs.joc.6b00343
31. [31]
  P. Qian, Z. Yan, Z. Zhou, et al., Org. Lett. 20 (2018) 6359–6363 doi: 10.1021/acs.orglett.8b02578
32. [32]
  Y.D. Wu, X. Geng, Q. Gao, et al., Org. Chem. Front. 3 (2016) 1430–1434 doi: 10.1039/C6QO00313C
33. [33]
  H. Wu, X. Guo, C. Yu, et al., Dyes Pigment. 176 (2020) 108209 doi: 10.1016/j.dyepig.2020.108209
34. [34]
  Y. Zhang, B. He, J. Liu, et al., Phys. Chem. Chem. Phys. 20 (2018) 9922–9929 doi: 10.1039/c8cp00260f
35. [35]
  M.Y. She, Z. Wang, T. Luo, et al., Chem. Sci. 9 (2018) 8065–8070 doi: 10.1039/c8sc03421d
36. [36]
  M. Yang, J. Deng, H. Su, et al., Mater. Chem. Front. 5 (2021) 406–417 doi: 10.1039/d0qm00536c
37. [37]
  J. Li, S. Zhang, H. Zou, Org. Chem. Front. 7 (2020) 1218–1223 doi: 10.1039/d0qo00274g
38. [38]
  S. Han, J. Thatte, D.J. Buzard, et al., J. Med. Chem. 56 (2013) 8224–8256 doi: 10.1021/jm4005626
39. [39]
  X. Li, T. Hua, K. Vemuri, et al., Cell 176 (2019) 459–467 doi: 10.1080/1536383x.2019.1608437
40. [40]
  B.W. Trotter, K.K. Nand, C.S. Burgey, et al., Bioorg. Med. Chem. Lett. 21 (2011) 2354–2358 doi: 10.1016/j.bmcl.2011.02.082
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沈阳化工大学材料科学与工程学院沈阳 110142

Construction and regulation of imidazo[1, 5-a]pyridines with AIE characteristics via iodine mediated Csp2−H or Csp−H amination

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通讯作者: 陈斌, bchen63@163.com

Construction and regulation of imidazo[1, 5-a]pyridines with AIE characteristics via iodine mediated Csp²−H or Csp−H amination