Chinese Journal of Organic Chemistry >
Synthesis and Luminescent Properties of 6-Methoxy-quinazolinone-pyridine Difluoroboron Dyes
Received date: 2019-01-03
Revised date: 2019-02-03
Online published: 2019-02-22
Supported by
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).
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.
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
[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] (a) Boens, N.; Leen, V.; Dehaen, W. Chem. Soc. Rev. 2012, 41, 1130.
(b) Zhang, Y.; Fu, Y.-Y.; Zhu, D.-F.; Xu, J.-Q.; He, Q.-G.; Cheng, J.-G. Chin. Chem. Lett. 2016, 27, 1429.
(c) Lu, B. W.; Meng, S. X.; Feng, Y. Q. Chin. J. Org. Chem. 2018, 38, 350(in Chinese). (卢博为, 孟舒献, 冯亚青, 有机化学, 2018, 38, 350.)
[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] (a) Frath, D.; Massue, J.; Ulrich, G.; Ziessel, R. Angew. Chem., Int. Ed. 2014, 53, 2290.
(b) Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
(c) Patalag, L. J.; Jones, P. G.; Werz, D. B. Angew. Chem., Int. Ed. 2016, 55, 13340.
(d) Wu, Y. Y.; Gou, G. Z.; Wu, X. X.; Yang, L. J.; Fu, W. F. Chin. J. Org. Chem. 2017, 37, 704(in Chinese). (吴云英, 苟高章, 伍贤学, 杨丽君, 傅文甫, 有机化学, 2017, 37, 704.)
[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] (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] (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] (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] Chen, Y. H.; Zhao, J. Z.; Guo, H. M.; Xie, L. J. J. Org. Chem. 2012, 77, 2192.
[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
[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
[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.
[13] Liu, H.; Lu, H.; Zhou, Z. K.; Shimizu, S.; Li, Z. F.; Kobayashic, N.; Shen, Z. Chem. Commun. 2015, 51, 1713.
[14] Kubota, Y.; Tsuzuki, T.; Funabiki, K.; Ebihara, M.; Matsui, M. Org. Lett. 2010, 12, 4010.
[15] Araneda, J. F.; Piers, W. E.; Heyne, B.; Parvez, M.; McDonald, R. Angew. Chem., Int. Ed. 2011, 50, 12214.
[16] Kubota, Y.; Ozaki, Y.; Funabiki, K.; Matsui, M. J. Org. Chem. 2013, 78, 7058.
[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.
[18] Zhu, C.; Guo, Z.-H.; Mu, A. U.; Liu, Y.; Wheeler, S. E.; Fang, L. J. Org. Chem. 2016, 81, 4347.
[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.
[20] Yang, L.; Shi, X.; Hu, B.-Q.; Wang, L.-X. Asian J. Org. Chem. 2016, 5, 494.
[21] Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456.
[22] Sun, H.; Zhong, C.; Bredas, J.-L. J. Chem. Theory Comput. 2015, 11, 3851.
[23] Gao, X.; Bai, S.; Fazzi, D.; Niehaus, T.; Barbatti, M.; Thiel, W. J. Chem. Theory Comput. 2017, 13, 515.
[24] Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580.
[25] Ando, Y.; Homma, Y.; Hiruta, Y.; Citterio, D. Dyes Pigm. 2009, 83, 198.
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