1,4-硼氮杂芳烃在中国的研究进展
收稿日期: 2023-04-20
修回日期: 2023-06-07
网络出版日期: 2023-06-26
基金资助
国家自然科学基金(22071181); 天津市自然科学基金(22JCYBJC00260)
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)
稠环芳烃及其衍生物在有机光电材料领域具有广泛应用, 杂原子掺杂可有效调节稠环芳烃的物理化学性质. 硼氮杂芳烃是稠环芳烃的重要成员. 基于硼原子和氮原子的相对位置, 硼氮杂芳烃可以分为三种异构体: 1,2-硼氮杂芳烃、1,3-硼氮杂芳烃和1,4-硼氮杂芳烃, 由于合成上的困难, 1,3-硼氮杂芳烃的研究相对较少. 近年来, 得益于1,4-硼氮杂芳烃在多重共振热活化延迟荧光材料方面潜力的发掘, 1,4-硼氮杂芳烃在国内外都取得了飞速发展. 我国有机化学及材料化学领域的学者们积极参与并推动了1,4-硼氮杂芳烃的快速发展, 在1,4-硼氮杂芳烃的结构开发和应用拓展方面开展了一系列原创性的工作, 取得了瞩目的成绩. 以1,4-硼氮芳烃的结构作为线索, 按照杂原子二元掺杂(B/N)骨架和三元掺杂(X/B/N)骨架分别进行论述, 综述了1,4-硼氮杂芳烃的合成发展历史和应用研究拓展, 最后对硼氮杂芳烃领域的未来发展与应用进行了展望.
关键词: 1,4-硼氮杂芳烃; 多重共振热活化延迟荧光; 有机硼化学
徐晓阳 , 刘美艳 , 李成龙 , 吴晓明 , 刘旭光 . 1,4-硼氮杂芳烃在中国的研究进展[J]. 有机化学, 2023 , 43(11) : 3826 -3843 . DOI: 10.6023/cjoc202304027
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.
| [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. |
/
| 〈 |
|
〉 |