An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters

doi:10.6023/cjoc202403054

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2504-2512.DOI: 10.6023/cjoc202403054 Previous Articles Next Articles

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窄化芘基发光分子半峰宽的合成策略

谢志鑫^a, 黎少玲^a, 刘威^a, 严楷^a(), 蒋涛^a, 刘一苇^a, Md. Monarul Islam^a^,^*(), 冯星^a^,^*()

a 广东工业大学材料与能源学院 510006
b 广东工业大学分析测试中心 510006
c 孟加拉国科学和工业研究理事会(BCSIR)化学研究部达卡-1205丹蒙迪孟加拉国

收稿日期:2024-05-14 修回日期:2024-06-22 发布日期:2024-07-02
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(21975054); 广东省基础与应用基础研究基金(2020A1515110992)

An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters

Zhixin Xie^a, Shaoling Li^a, Wei Liu^a, Kai Yan^a(), Tao Jiang^a, Yiwei Liu^a, Md. Monarul Islam^a(), Xing Feng^a()

a School of Materials and Energy, Guangdong University of Technology, Guangzhou 510006
b Analysis and Test Center, Guangdong University of Technology, Guangzhou 510006
c Synthesis Laboratory, Chemical Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka-1205, Bangladesh

Received:2024-05-14 Revised:2024-06-22 Published:2024-07-02
Contact: *E-mail: atc_yank@gdut.edu.cn; mmipavel@yahoo.com; hyxhn@sina.com
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21975054); Guangdong Basic and Applied Basic Research Foundation(2020A1515110992)

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Abstract

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

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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.

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Fig. & Tab. 5

Scheme 1. Synthetic route for target compounds 5a~5d

Figure 1. Computed molecular orbital plots (B3LYP/6-31G*) of 5a~5d

Compd.	ε_max/(L•mol^－1•cm^－1)	λ_max,PL/nm	τ/ns	Φ_f	α(AIE)^d	k_r^e/(10⁷ s^－1)	k_nr^f/(10⁷ s^－1)	FWHM/nm
5a	118379	505^a 490^b 477^c	5.05^a 9.28^b 3.35^c	0.53^a 0.19^b 0.31^c	0.58	10.49^a 2.04^b 9.25^c	9.31^a 8.73^b 20.60^c	84^a 68^b 57^c
5b	66312	475^a 476^b 483^c	1.02^a 2.18^b 2.41^c	0.01^a 0.37^b 0.50^c	50	0.98^a 16.97^b 20.74^c	97.05^a 28.90^b 20.75^c	81^a 79^c 76^c
5c	77805	469^a 464^b 484^c	2.64^a 2.01^b 2.57^c	0.64^a 0.31^b 0.38^c	0.59	24.24^a 15.42^b 14.78^c	13.63^a 34.33^b 24.11^c	67^a 57^b 49^c
5d	42776	502^a 507^b 512^c	3.81^a 2.85^b 4.61^c	0.69^a 0.09^b 0.32^c	0.46	18.11^a 3.15^b 6.94^c	8.13^a 31.93^b 14.75^c	106^a 82^b 68^c

Table 1. Photophysical properties of compounds 5a~5d

Figure 2. (A) UV-vis absorption spectra and (B) emission spectra of compounds 5 in THF (10－5 mol/L) at room temperature; (C) emission spectra of compounds 5 in the solid state; (D) quantum yields of compounds 5 in THF/H2O mixtures with water fractions (fw) of 0 (black), fw=99% (red) and in the solid state (blue); (E) fluorescence spectra of compound 5d recorded in six solvents at (ca. 10-5 mol/L); (F) plots of Stokes shift (?ν) vs ?f(ε,n) of compounds 5a~5d

Figure 3. (A) Emission spectra of 5b in THF/H2O mixtures with various water fractions (fw) (10－5 mol/L); (B) plot of the relative PL intensity I/I0 at different water fractions for 5b Inset: fluorescence images of 5b in THF/H2O mixtures at different fw (0 and 99%) values taken under 365 nm irradiation.

References 34

[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.
	(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).
	(赵洋, 陈盼盼, 韩立志, 王恩举, 有机化学, 2023, 43, 2454.) doi: 10.6023/cjoc202212004
[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. doi: 10.1021/cr100428a pmid: 21740071
[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.
	(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, Ö.; 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.; Pålsson, 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).
	(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
[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.

窄化芘基发光分子半峰宽的合成策略

An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters

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