Chinese Journal of Organic Chemistry >
Recent Advance of 1,4-BN Heteroaromatics in China
Received date: 2023-04-20
Revised date: 2023-06-07
Online published: 2023-06-26
Supported by
National Natural Science Foundation of China(22071181); Natural Science Foundation of Tianjin City(22JCYBJC00260)
Polycyclic aromatic hydrocarbons are widely used in optoelectronic materials, and heteroatom doping can effectively modulate the physicochemical properties of polycyclic aromatic hydrocarbons. Boron nitrogen (BN)-doped aromatics are important members of polycyclic aromatic hydrocarbons (PAHs) family. Based on the relative positions of boron and nitrogen atoms, BN-doped aromatics can be divided into three forms: 1,2-BN heteroaromatics, 1,3-BN heteroaromatics and 1,4-BN heteroaromatics. Despite the blooming researh of 1,2-BN heteroaromatics, the 1,3- and 1,4-BN heteroaromatics were much less studied. Owing to recent advances in multi-resonance thermally acitvated fluoresence (MR-TADF) materials based on 1,4-BN heteroaromatics, the research of 1,4-BN-heteroaromatics is currently ondergoing a renassiance. In particular, researchers from China have actively participated in and promoted the rapid development of 1,4-BN heteroaromatics, and the large number of recent publications also demonstrate the remarkable growth of the MR-TADF material based on 1,4-BN heteroaromatics. Taking the structure of 1,4-BN heteroaromatics as a clue, the synthesis and development history of 1,4-BN heteroaromatics are reviewed based on the heteroatom binary doping (B/N) framework and ternary doping (X/B/N) framework. Finally, the future development and application of 1,4-BN heteroaromatics are prospected.
Xiaoyang Xu , Meiyan Liu , Chenglong Li , Xiaoming Wu , Xuguang Liu . Recent Advance of 1,4-BN Heteroaromatics in China[J]. Chinese Journal of Organic Chemistry, 2023 , 43(11) : 3826 -3843 . DOI: 10.6023/cjoc202304027
| [1] | (a) Wang, C. L.; Dong, H. L.; Hu, W. P.; Liu, Y. Q.; Zhu, D. B., Chem. Rev. 2011, 112, 2208. |
| [1] | (b) Wu, W.; Liu, Y.; Zhu, D. Chem. Soc. Rev. 2010, 39, 1489. |
| [1] | (c) Anthony, J. E. Chem. Rev. 2006, 106, 5028. |
| [2] | (a) Jiang, W.; Li, Y.; Wang, Z. H. Chem. Soc. Rev. 2013, 42, 6113. |
| [2] | (b) Fukazawa, A.; Yamaguchi, S., Chem.-Asian. J. 2009, 4, 1386. |
| [3] | Maitlis, P. M. J. Chem. Soc. 1961, 425. |
| [4] | Hatakeyama, T.; Shiren, K.; Nakajima, K.; Nomura, S.; Nakatsuka, S.; Kinoshita, K.; Ni, J. P.; Ono, Y.; Ikuta, T. Adv. Mater. 2016, 28, 2777. |
| [5] | (a) Liang, X.; Yan, Z. P.; Han, H. B.; Wu, Z. G.; Zheng, Y. X.; Meng, H.; Zuo, J. L.; Huang, W. Angew. Chem. Inter. Ed. 2018, 57, 11316. |
| [5] | (b) Oda, S.; Kumano, W.; Hama, T.; Kawasumi, R.; Yoshiura, K.; Hetakeyama, T. Angew. Chem., Int. Ed. 2021, 60, 2882. |
| [6] | (a) Hall, D.; Suresh, S. M.; dos Santos, P. L.; Duda, E.; Bagnich, S.; Pershin, A.; Rajamalli, P.; Cordes, D. B.; Slawin, A. M. Z.; Beljonne, D.; K?hler, A.; Samuel, I. D. W.; Olivier, Y.; Zysman‐Col- man, E. Adv. Opt. Mater. 2019, 8, 1901627. |
| [6] | (b) Kothavale, S. S.; Lee, J. Y. Adv. Opt. Mater. 2020, 8, 2000922. |
| [6] | (c) Madayanad Suresh, S.; Hall, D.; Beljonne, D.; Olivier, Y.; Zysman-Colman, E. Adv. Funct. Mater. 2020, 30, 1908677. |
| [6] | (d) Chen, C.; Du, C. Z.; Wang, X. Y. Adv. Sci. 2022, 9, e2200707. |
| [6] | (e) Kim, H. J.; Yasuda, T. Adv. Opt. Mater. 2022, 10. 2201714. |
| [6] | (f) Shin, I.; Lim, H. N.; Hong, W. P. Synthesis 2022, 54, 570. |
| [6] | (g) Zhang, Y.; Du, C. Z.; Li, J. K.; Wang, X. Y. Chin. J. Org. Chem. 2023, 43, 1645. (in Chinese) |
| [6] | (张祎, 杜呈卓, 李继坤, 王小野, 有机化学, 2023, 43, 1645.) |
| [6] | (h) Jing, K.; Zhang, P. K.; Xu, S. M. Chin. J. Org. Chem. 2023, 43, 1742. (in Chinese) |
| [6] | (景科, 张攀科, 徐森苗, 有机化学, 2023, 43, 1742.) |
| [7] | Kranz, M.; Hampel, F.; Clark, T. J. Chem. Soc., Chem. Commun. 1992, 1247. |
| [8] | Agou, T.; Kobayashi, J.; Kawashima, T. Org. Let. 2006, 8, 2241. |
| [9] | (a) Agou, T.; Kobayashi, J.; Kawashima, T. Chem. Commun. 2007, 3204. |
| [9] | (b) Agou, T.; Kobayashi, J.; Kawashima, T. Org. Lett. 2009, 3534. |
| [9] | (c) Agou, T.; Arai, H.; Kawashima, T. Chem. Lett. 2010, 39, 612. |
| [9] | (d) Agou, T.; Sekine, M.; Kobayashi, J.; Kawashima, T. Chem.-Eur. J. 2009, 15, 5056. |
| [10] | Braunschweig, H.; Damme, A.; Jimenez-Halla, J. O. C.; Pfaffinger, B.; Radacki, K.; Wolf, J. Angew. Chem., Int. Ed. 2012, 51, 10034. |
| [11] | Xu, S. M.; Haeffner, F.; Li, B.; Zakharov, L. N.; Liu, S. Y. Angew. Chem., Int. Ed. 2014, 53, 6795. |
| [12] | Chinnapattu, M.; Sathiyanarayanan, K. I.; Iyer, P. S. RSC Adv. 2015, 5, 37716. |
| [13] | Liu, X.; Zhang, Y.; Li, B.; Zakharov, L. N.; Vasiliu, M.; Dixon, D. A.; Liu, S. Y. Angew. Chem., Int. Ed. 2016, 55, 8333. |
| [14] | Igarashi, T.; Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2017, 56, 2069. |
| [15] | Zhang, Y.; Zhang, D.; Wei, J.; Liu, Z.; Lu, Y.; Duan, L. Angew. Chem., Int. Ed. 2019, 58, 16912. |
| [16] | (a) Xu, Y.; Cheng, Z.; Li, Z.; Liang, B.; Wang, J.; Wei, J.; Zhang, Z.; Wang, Y. Adv. Opt. Mater. 2020, 8, 1902142. |
| [16] | (b) Xu, S.; Yang, Q. Q.; Zhang, Y.; Li, H.; Xue, Q.; Xie, G. H.; Gu, M. Z.; Jin, J. B.; Huang, L.; Chen, R. F. C. Chem. Lett. 2021, 32, 1372. |
| [17] | Hua, T.; Zhan, L.; Li, N.; Huang, Z.; Cao, X.; Xiao, Z.; Gong, S.; Zhou, C.; Zhong, C.; Yang, C. L. Chem.-Eur. J. 2021, 426. |
| [18] | (a) Zhang, Y.; Zhang, D.; Huang, T.; Gillett, A. J.; Liu, Y.; Hu, D.; Cui, L.; Bin, Z.; Li, G.; Wei, J.; Duan, L. Angew. Chem., Int. Ed. 2021, 60, 20498. |
| [18] | (b) Li, J. K.; Chen, X. Y.; Guo, Y. L.; Wang, X. C.; Sue, A. C.; Cao, X. Y.; Wang, X. Y. J. Am. Chem. Soc. 2021, 143, 17958. |
| [19] | Liu, F.; Cheng, Z.; Wan, L.; Feng, Z.; Liu, H.; Jin, H.; Gao, L.; Lu, P.; Yang, W. Small 2022, 18, e2106462. |
| [20] | Wu, X.; Huang, J.-W.; Su, B.-K.; Wang, S.; Yuan, L.; Zheng, W.-Q.; Zhang, H.; Zheng, Y. X.; Zhu, W.; Chou, P. T. Adv. Mater. 2022, 34, 2105080. |
| [21] | Qu, Y. K.; Zhou, D. Y.; Kong, F. C.; Zheng, Q.; Tang, X.; Zhu, Y. H.; Huang, C. C.; Feng, Z. Q.; Fan, J.; Adachi, C.; Liao, L. S.; Jiang, Z. Q. Angew. Chem., Int. Ed. 2022, 61, e202201886. |
| [22] | (a) Wang, Y.; Zhang, K.; Chen, F.; Wang, X.; Yang, Q.; Wang, S.; Shao, S.; Wang, L. X. Chin. J. Chem. 2022, 40, 2671. |
| [22] | (b) Li, Q.; Wu, Y.; Wang, X.; Yang, Q.; Hu, J.; Zhong, R.; Shao, S.; Wang, L. X. Chem.-Eur. J. 2022, 28, e2021042. |
| [23] | Liu, Y.; Xiao, X.; Huang, Z.; Yang, D.; Ma, D.; Liu, J.; Lei, B.; Bin, Z.; You, J. S. Angew. Chem., Int. Ed. 2022, 61, e202210210. |
| [24] | (a) Xu, S.; Zhang, Y.; Li, B.; Liu, S. Y. J. Am. Chem. Soc. 2016, 138, 14566. |
| [24] | (b) Zhang, Y.; Li, B.; Liu, S. Y. Angew. Chem., Int. Ed. 2020, 59, 15928. |
| [24] | (c) Wang, Z.; Wu, J.; Lamine, W.; Li, B.; Sotiropoulos, J. M.; Chrostowska, A.; Miqueu, K.; Liu, S. Y. Angew. Chem., Int. Ed. 2021, 60, 21231. |
| [25] | (a) Liang, X.; Tu, Z.-L.; Zheng, Y. X. Chem.-Eur. J. 2019, 25, 5623. |
| [25] | (b) Cai, X., Su, S. J. Adv. Funct. Mater. 2018, 28, 1802558. |
| [26] | Wang, Y. X.; Duan, Y. L.; Guo, R. D.; Ye, S. F.; Di, K. Y.; Zhang, W. Z.; Zhuang, S. Q.; Wang, L. Org. Electron. 2021, 97, 106275. |
| [27] | Yang, M.; I. Park, S.; Yasuda, T. J. Am. Chem. Soc. 2020, 142, 19468. |
| [28] | Xu, S.; Yang, Q. Q.; Zhang, Y.; Li, H.; Xue, Q.; Xie, G. H.; Gu, M. Z.; Jin, J. B.; Huang, L.; Chen, R. F. Chin. Chem. Lett. 2021, 32, 1372. |
| [29] | Xu, Y.; Wang, Q.; Cai, X.; Li, C. L.; Wang, Y. Adv. Mater. 2021, 33, e2100652. |
| [30] | Cai, S.; Tong, G. S. M.; Du, L.; So, G. K. M.; Hung, F. F.; Lam, T. L.; Cheng, G.; Xiao, H.; Chang, X.; Xu, Z. X.; Che, C. M. Angew. Chem., Int. Ed. 2022, 61, e202213392. |
| [31] | Chen, Z.; Zhong, C.; Han, J.; Miao, J.; Qi, Y.; Zou, Y.; Xie, G.; Gong, S.; Yang, C. L. Adv. Mater. 2022, 34, e2109147. |
| [32] | Xu, Y. C.; Li, C. L.; Li, Z. Q.; Wang, Q. Y.; Cai, X. L.; Wei, J. B.; Wang, Y. Angew. Chem., Int. Ed. 2020, 59, 17442. |
| [33] | Cai, X., Xu, Y., Pan, Y., Li, L., Pu, Y., Zhuang, X., Li, C. L, Wang, Y. Angew. Chem., Int. Ed. 2023, 62, e202216473. |
| [34] | (a) Zhao, J.; Ji, S.; Guo, H. RSC Adv. 2011, 1, 937. |
| [34] | (b) Gray, V.; Dzebo, D.; Abrahamsson, M.; Albinsson, B.; Moth- Poulsen, K. Phys. Chem. Chem. Phys. 2014, 16, 10345. |
| [35] | Wei, Y.; Pan, K.; Cao, X.; Li, Y.; Zhou, X.; Yang, C. L. CCS Chem. 2022, 4, 3852. |
| [36] | Zhang, Y.; Wei, J.; Zhang, D.; Yin, C.; Li, G.; Liu, Z.; Jia, X.; Qiao, J.; Duan, L. Angew. Chem., nt. Ed. 2022, 61, e202113206. |
| [37] | Wang, T.; Zou, Y.; Huang, Z.; Li, N.; Miao, J.; Yang, C. L. Angew. Chem., Int. Ed. 2022, 61, e202211172. |
| [38] | Luo, X. F.; Song, S. Q.; Ni, H. X.; Ma, H.; Yang, D.; Ma, D.; Zheng, Y. X.; Zuo, J. L. Angew. Chem., Int. Ed. 2022, 61, e202209984. |
| [39] | Zhang, Y.; Zhang, D.; Wei, J.; Hong, X.; Lu, Y.; Hu, D.; Li, G.; Liu, Z.; Chen, Y.; Duan, L. Angew. Chem., Int. Ed. 2020, 59, 17499. |
| [40] | Xu, Y.; Wang, Q.; Wei, J.; Peng, X.; Xue, J.; Wang, Z.; Su, S. J.; Wang, Y. Angew. Chem., Int. Ed. 2022, 61, e202204652. |
| [41] | Liu, J.; Zhu, Y.; Tsuboi, T.; Deng, C.; Lou, W.; Wang, D.; Liu, T.; Zhang, Q. Nat. Commun. 2022, 13, 4876. |
| [42] | Zhang, Y.; Wei, J.; Wang, L.; Huang, T.; Meng, G.; Wang, X.; Zeng, X.; Du, M.; Fan, T.; Yin, C.; Zhang, D.; Duan, L. Adv. Mater. 2022, e2209396. |
| [43] | Cheng, Y. C.; Fan, X. C.; Huang, F.; Xiong, X.; Yu, J.; Wang, K.; Lee, C. S.; Zhang, X. H. Angew. Chem., Int. Ed. 2022, 61, e202212575. |
| [44] | Wang, X.; Zhang, Y.; Dai, H.; Li, G.; Liu, M.; Meng, G.; Zeng, X.; Huang, T.; Wang, L.; Peng, Q.; Yang, D.; Ma, D.; Zhang, D.; Duan, L. Angew. Chem., Int. Ed. 2022, 61, e202206916. |
| [45] | Wu, T. L.; Lo, S. H.; Chang, Y. C.; Huang, M. J.; Cheng, C. H. ACS Appl. Mater. Interfaces 2019, 11, 10768. |
| [46] | Fan, T.; Zhang, Y.; Wang, L.; Wang, Q.; Yin, C.; Du, M.; Jia, X.; Li, G.; Duan, L. Angew. Chem., Int. Ed. 2022, e202213585. |
| [47] | Lv, X.; Miao, J.; Liu, M.; Peng, Q.; Zhong, C.; Hu, Y.; Cao, X.; Wu, H.; Yang, Y.; Zhou, C.; Ma, J.; Zou, Y.; Yang, C. Angew. Chem., Int. Ed. 2022, 61, e202201588. |
| [48] | Meng, G.; Dai, H.; Huang, T.; Wei, J.; Zhou, J.; Li, X.; Wang, X.; Hong, X.; Yin, C.; Zeng, X.; Zhang, Y.; Yang, D.; Ma, D.; Li, G.; Zhang, D.; Duan, L. Angew. Chem., Int. Ed. 2022, 61, e202207293. |
| [49] | Yang, Y.; Li, N.; Miao, J.; Cao, X.; Ying, A.; Pan, K.; Lv, X.; Ni, F.; Huang, Z.; Gong, S.; Yang, C. L. Angew. Chem., Int. Ed. 2022, 61, e202202227. |
| [50] | Fan, X. C.; Wang, K.; Shi, Y. Z.; Cheng, Y. C.; Lee, Y.-T.; Yu, J.; Chen, X. K.; Adachi, C.; Zhang, X. H. Nat. Photonics 2023, 17, 280. |
| [51] | Zhang, Y.; Li, G.; Wang, L.; Huang, T.; Wei, J.; Meng, G.; Wang, X.; Zeng, X.; Zhang, D.; Duan, L. Angew. Chem., Int. Ed. 2022, 61, e202202380. |
| [52] | Hua, T.; Miao, J.; Xia, H.; Huang, Z.; Cao, X.; Li, N.; Yang, C. L. Adv. Funct. Mater. 2022, 32, 2201032. |
| [53] | Hu, J.-J.; Luo, X.-F.; Zhang, Y.-P.; Mao, M.-X.; Ni, H.-X.; Liang, X.; Zheng, Y. X. J. Mater. Chem. C 2022, 10, 768. |
| [54] | Hu, Y. X.; Miao, J. S.; Hua, T.; Huang, Z. Y.; Qi, Y. Y.; Zou, Y.; Qiu, Y. T.; Xia, H.; Liu, H.; Cao, X. S.; Yang, C. L. Nat. Photonics 2022, 16, 803. |
| [55] | Liao, X. J.; Pu, D.; Yuan, L.; Tong, J.; Xing, S.; Tu, Z. L.; Zuo, J. L.; Zheng, W. H.; Zheng, Y. X. Angew. Chem., Int. Ed. 2023, e202217045. |
| [56] | Yang, W.; Li, N.; Miao, J.; Zhan, L.; Gong, S.; Huang, Z.; Yang, C. L. CCS Chem. 2022, 4, 3463. |
| [57] | Yan, Z. P.; Yuan, L.; Zhang, Y.; Mao, M.-X.; Liao, X. J.; Ni, H. X.; Wang, Z. H.; An, Z.; Zheng, Y. X.; Zuo, J. L. Adv. Mater. 2022, 34, 2204253. |
| [58] | Cai, X.; Xue, J.; Li, C.; Liang, B.; Ying, A.; Tan, Y.; Gong, S.; Wang, Y. Angew. Chem., Int. Ed. 2022, 61, e202200337. |
| [59] | Cao, X.; Pan, K.; Miao, J.; Lv, X.; Huang, Z.; Ni, F.; Yin, X.; Wei, Y.; Yang, C. J. Am. Chem. Soc. 2022, 144, 22976. |
| [60] | Liu, F.; Cheng, Z.; Jiang, Y.; Gao, L.; Liu, H.; Liu, H.; Feng, Z.; Lu, P.; Yang, W. Angew. Chem., Int. Ed. 2022, 61, e202116927. |
/
| 〈 |
|
〉 |