Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2479-2486.DOI: 10.6023/cjoc202403038 Previous Articles Next Articles
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黄凯航a, 尹理b, 姜青云a, 汪乾c,*(), 石光a, 许炳佳a,*(
)
收稿日期:
2024-06-04
修回日期:
2024-06-29
发布日期:
2024-07-10
基金资助:
Kaihang Huanga, Li Yinb, Qingyun Jianga, Qian Wangc(), Guang Shia, Bingjia Xua(
)
Received:
2024-06-04
Revised:
2024-06-29
Published:
2024-07-10
Contact:
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Kaihang Huang, Li Yin, Qingyun Jiang, Qian Wang, Guang Shi, Bingjia Xu. Efficient Thermally Activated Delayed Fluorescence Materials with Aggregation-Induced Emission for Lipid Droplet Imaging[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2479-2486.
Compd. | λabs,sla/nm | λem,slb/nm | λem,sc/nm | τflu.d/ns | τTADFe/μs | ΦPL,sf/% | αAIEg | ΔESTh/eV |
---|---|---|---|---|---|---|---|---|
1 | 396 | 548 | 519 | 11.26 | N/A | 24.1 | 42.6 | 0.59 |
2 | 390 | 606 | 540 | 14.65 | N/A | 24.0 | 130.9 | 0.18 |
3 | 394 | 640 | 547 | 47.60 | 4.60 | 46.5 | 57.8 | 0.05 |
Compd. | λabs,sla/nm | λem,slb/nm | λem,sc/nm | τflu.d/ns | τTADFe/μs | ΦPL,sf/% | αAIEg | ΔESTh/eV |
---|---|---|---|---|---|---|---|---|
1 | 396 | 548 | 519 | 11.26 | N/A | 24.1 | 42.6 | 0.59 |
2 | 390 | 606 | 540 | 14.65 | N/A | 24.0 | 130.9 | 0.18 |
3 | 394 | 640 | 547 | 47.60 | 4.60 | 46.5 | 57.8 | 0.05 |
[1] |
(a) Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Natur. 2012, 492, 234.
|
(b) Mehes, G.; Nomura, H.; Zhang, Q.; Nakagawa, T.; Adachi, C. Angew. Chem., Int. Ed. 2012, 51, 11311.
|
|
(c) Zhu, Z.; Tian, D.; Gao, P.; Wang, K.; Li, Y.; Shu, X.; Zhu, J.; Zhao, Q. J. Am. Chem. Soc. 2018, 140, 17484.
|
|
(d) Yang, Z.; Mao, Z.; Xie, Z.; Zhang, Y.; Liu, S.; Zhao, J.; Xu, J.; Chi, Z.; Aldred, M. P. Chem. Soc. Rev. 2017, 46, 915.
|
|
(e) Zhang, Y.; Nie, F.; Zhou, L.; Wang, X.; Liu, Y.; Huo, Y.; Chen, W.; Zhao, Z. Chin. J. Org. Chem. 2023, 43, 3876 (in Chinese).
|
|
(张越华, 聂飞, 周路, 王晓烽, 刘源, 霍延平, 陈文铖, 赵祖金, 有机化学, 2023, 43, 3876.)
doi: 10.6023/cjoc202303022 |
|
[2] |
(a) Chen, Y.; Xu, C.; Xu, B.; Mao, Z.; Li, J.-A.; Yang, Z.; Peethani, N. R.; Liu, C.; Shi, G.; Gu, F. L.; Zhang, Y.; Chi, Z. Mater. Chem. Front. 2019, 3, 1800.
|
(b) Liang, Y.; Hu, P.; Zhang, H.; Yang, Q.; Wei, H.; Chen, R.; Yu, J.; Liu, C.; Wang, Y.; Luo, S.; Shi, G.; Chi, Z.; Xu, B. Angew. Chem., Int. Ed. 2024, 63, e202318516.
|
|
[3] |
(a) Liu, Y. C.; Li, C. S.; Ren, Z. J.; Yan, S. K.; Bryce, M. R. Nat. Rev. Mater. 2018, 3, 18020.
|
(b) Xiao, Y. X.; Wang, H. L.; Xie, Z. L.; Shen, M. Y.; Huang, R. J.; Miao, Y. C.; Liu, G. Y.; Yu, T.; Huang, W. Chem. Sci. 2022, 13, 8906.
|
|
(c) Shi, Y. Z.; Wu, H.; Wang, K.; Yu, J.; Ou, X. M.; Zhang, X. H. Chem. Sci. 2022, 13, 3625.
|
|
[4] |
(a) Yang, Y.; Liang, Y.; Zheng, Y.; Li, J. A.; Wu, S.; Zhang, H.; Huang, T.; Luo, S.; Liu, C.; Shi, G.; Sun, F.; Chi, Z.; Xu, B. Angew. Chem., Int. Ed. 2022, 61, e202201820.
|
(b) Liang, Y.; Xu, C.; Zhang, H.; Wu, S.; Li, J. A.; Yang, Y.; Mao, Z.; Luo, S.; Liu, C.; Shi, G.; Sun, F.; Chi, Z.; Xu, B. Angew. Chem., Int. Ed. 2023, 62, e202217616.
|
|
(c) Tao, Y.; Yuan, K.; Chen, T.; Xu, P.; Li, H.; Chen, R.; Zheng, C.; Zhang, L.; Huang, W. Adv. Mater. 2014, 26, 7931.
|
|
[5] |
(a) Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718.
doi: 10.1021/acs.chemrev.5b00263 pmid: 26492387 |
(b) Xu, H.; Han, P.; Qin, A.; Tang, B. Z. Acta Chim. Sinic. 2023, 81, 1420 (in Chinese).
pmid: 26492387 |
|
(徐赫, 韩鹏博, 秦安军, 唐本忠, 化学学报, 2023, 81, 1420.)
doi: 10.6023/A23050232 pmid: 26492387 |
|
[6] |
Xu, S.; Liu, T.; Mu, Y.; Wang, Y. F.; Chi, Z.; Lo, C. C.; Liu, S.; Zhang, Y.; Lien, A.; Xu, J. Angew. Chem., Int. Ed. 2015, 54, 874.
|
[7] |
Huang, J.; Nie, H.; Zeng, J.; Zhuang, Z.; Gan, S.; Cai, Y.; Guo, J.; Su, S. J.; Zhao, Z.; Tang, B. Z. Angew. Chem., Int. Ed. 2017, 56, 12971.
|
[8] |
(a) Xu, B.; Mu, Y.; Mao, Z.; Xie, Z.; Wu, H.; Zhang, Y.; Jin, C.; Chi, Z.; Liu, S.; Xu, J.; Wu, Y.-C.; Lu, P.-Y.; Lien, A.; Bryce, M. R. Chem. Sci. 2016, 7, 2201.
pmid: 28345346 |
(b) Xu, B.; Song, Z.; Zhang, M.; Zhang, Q.; Jiang, L.; Xu, C.; Zhong, L.; Su, C.; Ban, Q.; Liu, C.; Sun, F.; Zhang, Y.; Chi, Z.; Zhao, Z.; Shi, G. Chem. Sci. 2021, 12, 15556.
pmid: 28345346 |
|
(c) Zheng, Y. T.; Zuo, L. Q.; Zhang, L. T.; Huang, Z. H.; Li, S. F.; Yang, Z.; Mao, Z.; Luo, S. L.; Liu, C.; Sun, F. Q.; Shi, G.; Chi, Z. G.; Xu, B. J. Chin. Chem. Lett. 2022, 33, 4536.
pmid: 28345346 |
|
(d) Tsujimoto, H.; Ha, D. G.; Markopoulos, G.; Chae, H. S.; Baldo, M. A.; Swager, T. M. J. Am. Chem. Soc. 2017, 139, 4894.
doi: 10.1021/jacs.7b00873 pmid: 28345346 |
|
(e) Yang, S. Y.; Feng, Z. Q.; Fu, Z.; Zhang, K.; Chen, S.; Yu, Y. J.; Zou, B.; Wang, K.; Liao, L. S.; Jiang, Z. Q. Angew. Chem., Int. Ed. 2022, 61, e202206861.
pmid: 28345346 |
|
(f) Zhang, T.; Xiao, Y.; Wang, H.; Kong, S.; Huang, R.; Ka-Man Au, V.; Yu, T.; Huang, W. Angew. Chem., Int. Ed. 2023, 62, e202301896.
pmid: 28345346 |
|
(g) Sano, Y.; Shintani, T.; Hayakawa, M.; Oda, S.; Kondo, M.; Matsushita, T.; Hatakeyama, T. J. Am. Chem. Soc. 2023, 145, 11504.
pmid: 28345346 |
|
(h) Fu, Y.; Liu, H.; Tang, B. Z.; Zhao, Z. Nat. Commun. 2023, 14, 2019.
pmid: 28345346 |
|
(i) Cho, H. H.; Gorgon, S.; Hung, H. C.; Huang, J. Y.; Wu, Y. R.; Li, F.; Greenham, N. C.; Evans, E. W.; Friend, R. H. Adv. Mater. 2023, 35, 2303666.
pmid: 28345346 |
|
[9] |
Liu, Z.; Zou, H.; Zhao, Z.; Zhang, P.; Shan, G. G.; Kwok, R. T. K.; Lam, J. W. Y.; Zheng, L.; Tang, B. Z. ACS Nan. 2019, 13, 11283.
|
[10] |
Zheng, Z.; Yang, Y.; Wang, P.; Gou, X.; Gong, J.; Wu, X.; Bao, Z.; Liu, L.; Zhang, J.; Zou, H.; Zheng, L.; Tang, B. Z. Adv. Funct. Mater. 2023, 33, 2303627.
|
[11] |
(a) Ma, D.; Zhuang, W.; Liu, Q.; Chen, J.; Li, C.; Li, S.; Chen, M. Chem. Eng. J. 2023, 476, 146792.
|
(b) Zhao, Y.; Zhang, X.; Yang, Y.; Zhu, L.; Zhou, Y. Acta Chim. Sinic. 2024, 82, 265 (in Chinese).
|
|
(赵玉强, 张霞, 杨芸如, 朱立平, 周莹, 化学学报, 2024, 82, 265.)
doi: 10.6023/A23100457 |
|
(c) Zeng, C.; Hu, P.; Wang, B.; Fang, W.; Zhao, K.; Donnio, B. Acta Chim. Sinic. 2023, 81, 469 (in Chinese).
|
|
(曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, Donnio Bertrand, 化学学报, 2023, 81, 469.)
doi: 10.6023/A23010006 |
|
[12] |
Li, X.; Baryshnikov, G.; Ding, L.; Bao, X.; Li, X.; Lu, J.; Liu, M.; Shen, S.; Luo, M.; Zhang, M.; Agren, H.; Wang, X.; Zhu, L. Angew. Chem., Int. Ed. 2020, 59, 7548.
|
[13] |
(a) Li, T.; Yang, D.; Zhai, L.; Wang, S.; Zhao, B.; Fu, N.; Wang, L.; Tao, Y.; Huang, W. Adv. Sci. 2017, 4, 1600166.
|
(b) Ni, F.; Zhu, Z.; Tong, X.; Zeng, W.; An, K.; Wei, D.; Gong, S.; Zhao, Q.; Zhou, X.; Yang, C. Adv. Sci. 2019, 6, 1801729.
|
|
(c) Yu, M.; Zhao, W.; Ni, F.; Zhao, Q.; Yang, C. Adv. Opt. Mater. 2022, 10, 2102437.
|
|
(d) Qi, S.; Kim, S.; Nguyen, V.-N.; Kim, Y.; Niu, G.; Kim, G.; Kim, S.-J.; Park, S.; Yoon, J. ACS Appl. Mater. Interface. 2020, 12, 51293.
|
|
[14] |
(a) Xu, S.; Wu, L.-L.; Wang, X.; Hu, H.-Y. TrA., Trends Anal. Chem. 2023, 169, 117356.
|
(b) Ni, F.; Li, N.; Zhan, L.; Yang, C. Adv. Opt. Mater. 2020, 8, 1902187.
|
|
[15] |
(a) Feng, X.; Zhu, L.; Yue, B. Acta Chim. Sinic. 2022, 80, 647 (in Chinese).
|
(冯锡成, 朱亮亮, 岳兵兵, 化学学报, 2022, 80, 647.)
doi: 10.6023/A22010015 |
|
(b) Liu, B.; Chen, P. Acta Chim. Sinic. 2022, 80, 929 (in Chinese).
|
|
(刘斌, 陈磅宽, 化学学报, 2022, 80, 929.)
doi: 10.6023/A22030122 |
|
(c) Zhang, L.; Wang, Y.; Zhu, G.; Dai, W.; Zhao, Z.; Zhao, Y.; Zhi, J.; Dong, Y. Acta Chim. Sinic. 2022, 80, 282 (in Chinese).
|
|
(张璐璐, 王媛媛, 朱贵楠, 戴文博, 赵紫璇, 赵盈, 支俊格, 董宇平, 化学学报, 2022, 80, 282.)
doi: 10.6023/A21120556 |
|
(d) Lu, H.; Ma, L.; Ma, H. Chin. J. Org. Chem. 2023, 43, 4075 (in Chinese).
|
|
(鲁会名, 马拉毛草, 马恒昌, 有机化学, 2023, 43, 4075.)
doi: 10.6023/cjoc202305010 |
|
[16] |
Kim, Y. KR 2023032996, 2023.
|
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