Citation: Zhou Jia, Liu Lu, Zhong Cheng, Fu Yang, Song Zhibin, Peng Yiyuan. Synthesis and Luminescent Properties of 6-Methoxy-quinazolinone-pyridine Difluoroboron Dyes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1444-1449. doi: 10.6023/cjoc201901003 shu

Synthesis and Luminescent Properties of 6-Methoxy-quinazolinone-pyridine Difluoroboron Dyes

Zhou Jia ^a ,
Liu Lu ^a ,
Zhong Cheng ^b ,
Fu Yang ^a ,
Song Zhibin ^a,, ,
Peng Yiyuan ^a

a.
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
b.
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072

Corresponding author: Song Zhibin, zbsong@jxnu.edu.cn
Received Date: 3 January 2019
Revised Date: 3 February 2019
Available Online: 22 May 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21606116, 51873160), the Natural Science Foundations of Jiangxi Province (No. 20161BAB213070) and the Department of Education of Jiangxi Province (No. GJJ170176)the National Natural Science Foundation of China 21606116the Natural Science Foundations of Jiangxi Province 20161BAB213070the Department of Education of Jiangxi Province GJJ170176the National Natural Science Foundation of China 51873160

Figures(6)

6-Methoxyquinazolinone-pyridine difluoroboron dyes (BODIQPys) have been synthesized in two simple steps with 2-amino-5-methoxybenzamide and 2-methylpyridines as starting materials. These quinazolinone-based difluoroboron (BF₂) complexes exhibited highly efficient green luminescence and remarkable fluorescence in the solid-state with very large Stokes shift (Δλ up to 220 nm in MeCN). The introduction of methoxy group at 6-position of BODIQPy caused the red-shifted emission by the enhancement of charge transfer property. The introduction of halogen atom at pyridine moiety of BODIQPy can tune the LUMO levels in regularity while their HOMO levels remain intact.
- quinazolinone,
- difluoroboron complexes,
- fluorescent dyes,
- solid state luminescence
1. [1]
  (a) Bessette, A.; Hanan, G. S. Chem. Soc. Rev. 2014, 43, 3342.
  (b) Bozdemir, O. A.; Erbas-Cakmak, S. O.; Ekiz, O.; Dana, A.; Akkaya, E. U. Angew. Chem., Int. Ed. 2011, 50, 10907.
2. [2]
3. [3]
  (a) Fan, J.; Hu, M.; Zhan, P.; Peng, X. Chem. Soc. Rev. 2013, 42, 29.
  (b) Wu, X.; Zhu, W. Chem. Soc. Rev. 2015, 44, 4179.
4. [4]
5. [5]
  (a) Zhao, J. Z.; Xu, K. J.; Yang, W. B.; Wang, Z. J.; Zhong, F. F. Chem. Soc. Rev. 2015, 44, 8904.
  (b) Yu, C. J.; Wu, Q. H.; Wang, J.; Wei, Y.; Hao, E. H.; Jiao, L. J. J. Org. Chem. 2016, 81, 3761.
6. [6]
  (a) Chen, P.-Z.; Niu, L.-Y.; Chen, Y.-Z.; Yang, Q.-Z. Coord. Chem. Rev. 2017, 350, 196.
  (b) Kolemen, S.; Akkaya, E. U. Coord. Chem. Rev. 2018, 354, 121.
  (c) Chen, P.-Z.; Zhang, H.; Niu, L.-Y.; Zhang, Y.; Chen, Y.-Z.; Fu, H.-B.; Yang Q.-Z. Adv. Funct. Mater. 2017, 27, 1700332.
7. [7]
  (a) Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem., Int. Ed. 2008, 47, 1184.
  (b) Xu, S.; Evans, R. E.; Liu, T.; Zhang, G.; Demas, J. N.; Trindle, C. O.; Fraser, C. L. Inorg. Chem. 2013, 52, 3597.
8. [8]
  (a) Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891.
  (b) Lu, H.; Mack, J.; Yang, Y.; Shen, Z. Chem. Soc. Rev. 2014, 43, 4778.
  (c) Choi, S.; Bouffard, J.; Kim, Y. Chem. Sci. 2014, 5, 751.
9. [9]
  Chen, Y. H.; Zhao, J. Z.; Guo, H. M.; Xie, L. J. J. Org. Chem. 2012, 77, 2192. doi: 10.1021/jo202215x
10. [10]
  Fei, Q.; Gu, X. F.; Liu, Y. J.; Shi, B.; Liu, H. Y.; Xu, G.; Li, C. B.; Shi, P.; Zhao, C. C. Org. Biomol. Chem. 2017, 15, 4072 doi: 10.1039/C7OB00383H
11. [11]
  Hu, R. R.; Azael Gómez-Durán, C. F.; Lam, J. W. Y.; Belmonte- Vázquez, J. L.; Deng, C. M.; Chen, S. J.; Ye, R. Q.; Peña- Cabrera, E.; Zhong, Y. C.; Wong, K. S.; Tang, B. Z. Chem. Commun. 2012, 48, 10099 doi: 10.1039/c2cc35188a
12. [12]
  Azael Gómez-Durán, C. F.; Hu, R. R.; Feng, G. X.; Li, T. Z.; Bu, F.; Arseneault, M.; Liu, B.; Peña-Cabrera, E.; Tang, B. Z. ACS Appl. Mater. Interfaces 2015, 7, 15168. doi: 10.1021/acsami.5b05033
13. [13]
  Liu, H.; Lu, H.; Zhou, Z. K.; Shimizu, S.; Li, Z. F.; Kobayashic, N.; Shen, Z. Chem. Commun. 2015, 51, 1713. doi: 10.1039/C4CC06704E
14. [14]
  Kubota, Y.; Tsuzuki, T.; Funabiki, K.; Ebihara, M.; Matsui, M. Org. Lett. 2010, 12, 4010. doi: 10.1021/ol101612z
15. [15]
  Araneda, J. F.; Piers, W. E.; Heyne, B.; Parvez, M.; McDonald, R. Angew. Chem., Int. Ed. 2011, 50, 12214. doi: 10.1002/anie.v50.51
16. [16]
  Kubota, Y.; Ozaki, Y.; Funabiki, K.; Matsui, M. J. Org. Chem. 2013, 78, 7058. doi: 10.1021/jo400879g
17. [17]
  Nosova, E. V.; Moshkina, T. N.; Lipunova, G. N.; Baklanova, I. V.; Slepukhin, P. A.; Charushin, V. N. J. Fluorine Chem. 2015, 175, 145. doi: 10.1016/j.jfluchem.2015.04.010
18. [18]
  Zhu, C.; Guo, Z.-H.; Mu, A. U.; Liu, Y.; Wheeler, S. E.; Fang, L. J. Org. Chem. 2016, 81, 4347. doi: 10.1021/acs.joc.6b00238
19. [19]
  Zhou, J.; Liu, L.; Pan, Y.; Zhu, Q. Y.; Lu, Y. J.; Wei, J. C.; Luo, K.; Fu, Y.; Zhong, C.; Peng, Y. Y.; Song, Z. B. Chem.-Eur. J. 2018, 24, 17897. doi: 10.1002/chem.v24.68
20. [20]
  Yang, L.; Shi, X.; Hu, B.-Q.; Wang, L.-X. Asian J. Org. Chem. 2016, 5, 494. doi: 10.1002/ajoc.201600041
21. [21]
  Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456. doi: 10.1002/jcc.v32.7
22. [22]
  Sun, H.; Zhong, C.; Bredas, J.-L. J. Chem. Theory Comput. 2015, 11, 3851. doi: 10.1021/acs.jctc.5b00431
23. [23]
  Gao, X.; Bai, S.; Fazzi, D.; Niehaus, T.; Barbatti, M.; Thiel, W. J. Chem. Theory Comput. 2017, 13, 515. doi: 10.1021/acs.jctc.6b00915
24. [24]
  Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580. doi: 10.1002/jcc.v33.5
25. [25]
  Ando, Y.; Homma, Y.; Hiruta, Y.; Citterio, D. Dyes Pigm. 2009, 83, 198. doi: 10.1016/j.dyepig.2009.04.008
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