Chinese Journal of Organic Chemistry >
An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters
Received date: 2024-05-14
Revised date: 2024-06-22
Online published: 2024-07-02
Supported by
National Natural Science Foundation of China(21975054); Guangdong Basic and Applied Basic Research Foundation(2020A1515110992)
The construction of high color purity and high resolution organic light-emitting diodes (OLEDs) is facilitated by the development of highly-efficient organic luminescent materials with narrow-band emission. Herein, in order to address the problem of broad emission spectra of organic luminescent materials, an effective molecular design strategy is presented to reduce the full width at half maximum (FWHM) of emission by integrating the steric hindrance effect in the pyrene system. As the bulky group was introduced into the 2-position, compounds 5 not only show a relative high quantum yield (>0.31) in the solid state, but also can suppress the molecular rotation of triphenylamine (TPA) at the 3-position to narrow the FWHM in the solid state compared to that in solution. Compound 5c containing biphenyl units exhibits a maximum emission peak at 484 nm with a quantum yield of 0.38 and FWHM value of 49 nm in the solid state.
Key words： aggregation-induced emission; pyrene; narrow-band emission; steric effect
Zhixin Xie , Shaoling Li , Wei Liu , Kai Yan , Tao Jiang , Yiwei Liu , Md. Monarul Islam , Xing Feng . An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters[J]. Chinese Journal of Organic Chemistry, 2024 , 44(8) : 2504 -2512 . DOI: 10.6023/cjoc202403054
| [1] | Huang, Y.; Jia, M. J.; Li, C.; Yang, Y.; He, Y. L.; Luo, Y. J.; Huang, Y.; Zhou, L.; Lu, Z. Chem. Commun. 2024, 60, 3194. |
| [2] | Jung, M. H.; Seon, H. H.; Ambika, P.; Ji-Eun, J.; Han, Y. W. NPG Asia Mater. 2021, 13, 53. |
| [3] | Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361. |
| [4] | Tu, L. J.; Xie, Y. J.; Li, Z.; Tang, B. Z. SmartMa. 2021, 2, 326. |
| [5] | (a) Jiang, G.; Liu, H.; Liu, H.; Ke, G.; Ren, T. B.; Xiong, B.; Zhang, X. B.; Yuan, L. Angew. Chem. Int. Ed. 2023, e202315217. |
| [5] | (b) Huang, Z.; Huang, C.; Tang, Y.; Xiao, Z.; Li, N.; Hua, T.; Cao, X.; Zhou, C.; Wu, C.; Yang, C. Dyes Pig.. 2022, 197, 109860. |
| [6] | Yang, G.; Ran, Y.; Wu, Y.; Chen, M.; Bin, Z.; You, J. Aggregat. 2022, 3, e127. |
| [7] | Zhao, Y.; Chen, P. P.; Han, L. Z.; Wang, E. J. Chin. J. Org. Chem. 2023, 43, 2454 (in Chinses). |
| [7] | (赵洋, 陈盼盼, 韩立志, 王恩举, 有机化学, 2023, 43, 2454.) |
| [8] | Luo, J. D.; Xie, Z. L.; Lam, J. W. Y.; Cheng, L.; Chen, H. Y.; Qiu, C. F.; Kwok, H. S.; Zhan, X. W.; Liu, Y. Q.; Zhu, D. B.; Tang, B. Z. Chem. Commun. 2001, 1740. |
| [9] | Zhou, P. W.; Han, K. Aggregat. 2022, 3, e160. |
| [10] | Xu, H.; Cheng, P. Aggregat. 2024, e518. |
| [11] | Zhang, S. W.; Li, D.; Wang, X. Y.; Fan, J.; Wang, T.; Yu, S. K.; Liao, W. Y.; Jia, X. D.; Yuan, Y. Luminescenc. 2021, 36, 958. |
| [12] | Leung, N. L. C.; Xie, N.; Yuan, W.; Liu, Y.; Wu, Q.; Peng, Q.; Miao, Q.; Lam, J. W. Y.; Tang, B. Z. Chem.-Eur. J. 2014, 20, 15349. |
| [13] | Gui, Y. X.; Chen, K. Y.; Sun, Y.; Tan, Y. H.; Luo, W. S.; Zhu, D. X.; Xiong, Y.; Yan, D. Y.; Wang, D.; Tang, B. Z. Chin. J. Chem. 2022, 40, 1249. |
| [14] | Chen, Y.; Lam, J. W. Y.; Kwok, R. T. K.; Liu, B.; Tang, B. Z. Mater. Horiz. 2019, 6, 428. |
| [15] | Feng, X.; Wang, X. H.; Redshaw, C.; Tang, B. Z. Chem. Soc. Rev. 2023, 52, 6715. |
| [16] | Figueira-Duarte, T. M.; Müllen, K. Chem. Rev. 2011, 111, 7260. |
| [17] | Islam, M. M.; Hu, Z.; Wang, Q. S.; Redshaw, C.; Feng, X. Mater. Chem. Front. 2019, 3, 762. |
| [18] | Liu, Y. W.; Zhang, J. Y.; Wang, X. H.; Xie, Z. X.; Zheng, H.; Zhang, H.; Cai, X. M.; Zhao, Y.; Redshaw, C.; Min, Y. G.; Feng, X. J. Org. Chem. 2024, 89, 3319. |
| [19] | Wang, X. H.; Zhang, J. Y.; Mao, X. Y.; Liu, Y. W.; Li, R. K.; Bai, J.; Zhang, J.; Redshaw, C.; Feng, X.; Tang, B. Z. J. Org. Chem. 2022, 87, 8503. |
| [20] | (a) Wang, Z. Y.; Liu, B.; Zhao, J. W.; Ruan, G. L.; Tao, S. L.; Tong, Q. X. Org. Electron. 2018, 52, 89. |
| [20] | (b) Zhang, L.; Zhao, H.; Hu, M.; Wang, X.; Hu, L.; Mao, H.; Yuan, Z.; Ma, W.; Chen, Y. Smal. 2021, 17, 2103537. |
| [21] | Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr. J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, ?.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A 08; Gaussian, Inc., Wallingford, C., 2009. |
| [22] | Feng, X.; Hu, J. Y.; Yi, L.; Seto, N.; Tao, Z.; Redshaw, C.; Elsegood, M. R. J.; Yamato, T. Chem. Asian J. 2012, 7, 2854. |
| [23] | Crawford, A. G.; Dwyer, A. D.; Liu, Z. Q.; Steffen, A.; Beeby, A.; P?lsson, L.-O.; Tozer, D. J.; Marder, T. B. J. Am. Chem. Soc. 2011, 133, 13349. |
| [24] | Thomas, K. R. J.; Maurya, A.; Nagar, M. R.; Jou, J-H. Dyes Pig.. 2023, 216, 111373. |
| [25] | Song, X. Y.; Wang, M.; Liu, W.; Zheng, H.; Redshaw, C.; Feng, X.; Zhao, Z. J.; Tang, B. Z. Dyes Pig.. 2023, 219, 111532. |
| [26] | Ha, J. M.; Hur, S. H.; Pathak, A.; Jeong, J-E.; Woo, H. Y. NPG Asia Mate.. 2021, 13, 53. |
| [27] | Liu, W.; Li, S. L.; Xie, Z. X.; Huang, K. W.; Yan, K.; Zhao, Y.; Redshaw, C.; Feng, X.; Tang, B. Z. Adv. Opt. Mater. 2024, 2400301. |
| [28] | Jiang, H.; Li, H. L.; Jin, J. B.; Bodedla, G. B.; Tao, P.; Ma, D. G.; Wong, W.-Y. J. Mater. Chem. C. 2023, 11, 6438. |
| [29] | Zhu, H. C.; Huang, J. Y.; Kong, L.; Tian, Y. P.; Yang, J. X. Dyes Pig.. 2018, 51, 140. |
| [30] | Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jp.. 1956, 29, 465. |
| [31] | Lippert, E.; Bunsenges, B. Phys. Chem. 1957, 61, 962. |
| [32] | Zhang, L. L.; Wang, Y. Y.; Zhu, G. N.; Dai, W. B.; Zhao, Z. X.; Zhao, Y.; Zhi, J. G.; Dong, Y. P. Acta Chim. Sinic. 2022, 80, 282 (in Chinese). |
| [32] | (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.) |
| [33] | Liu, J. k.; Zhang, H. K.; Hu, L. R.; Wang, J.; Lam, J. W. Y.; Blancafort, L.; Tang, B. Z. J. Am. Chem. Soc. 2022, 144, 7901. |
| [34] | Xie, Z. X.; Liu, W.; Liu, Y. W.; Song, X. Y.; Zheng, H.; Su, X.; Redshaw, C.; Feng, X. J. Org. Chem. 2024, 89, 1681. |
/
| 〈 |
|
〉 |
