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

doi:10.6023/cjoc202403054

Chinese Journal of Organic Chemistry Previous Articles Next Articles

ARTICLE

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, Islam, Monarul M.^*,b, 冯星^*,a

^a广东工业大学,广东省广州市番禺区广州大学城外环西路100号,510006
^bSynthesis Laboratory, Chemical Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka-1205, Bangladesh

收稿日期:2024-05-14 修回日期:2024-06-22

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

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

^aGuangdong University of Technology, Guangzhou 510006, P. R. China. E-mail: hyxhn@sina.com
^bSynthesis Laboratory, Chemical Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka-1205, Bangladesh. E-mail: mmipavel@yahoo.com

Received:2024-05-14 Revised:2024-06-22
Contact: E-mail: atc_yank@gdut.edu.cn (Yan K.), mmipavel@yahoo.com (Islam M.M.) and hyxhn@sina.com (Feng X.)
About author:^#Z. Xin and S. Li contributed equally to this work.
Supported by:
National Natural Science Foundation of China (21975054), the Guangzhou Basic and Applied Basic Research Foundation (2023A04J1372).

1. .pdf(4874KB)

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, we present an effective molecular design strategy 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, the 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 3-position to narrow the FWHM in solid state compared to that in solution. And the compound 5c containing biphenyl units exhibit a maximum emission peak at 484 nm with 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

Cite this article

Xie, Zhixin, Li, Shaoling, Liu, Wei, Yan, Kai, Jiang, Tao, Liu, Yiwei, Islam, Md. Monarul, Feng, Xing. An Efficient Approach to Narrow the Emission Band of Pyrene-based Emitters[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202403054.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.;S, 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, 5361-5388.
[4] Tu L. J.; Xie Y. J.; Li Z.; Tang B. Z.SmartMat.2021,2, 326-346.
[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. Pigm. 2022,197, 109860.
[6] Yang G.; Ran Y.; Wu Y.; Chen M.; Bin Z.; You J.Aggregate.2022,3, e127.
[7] Zhao Y.; Chen P. P.; Han L. Z.; Wang, E. J. Chin.Chin. J. Org. Chem.2023,43, 2454-2461.
[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, 1740-1741.
[9] Zhou P. W.; Han. K.Aggregate.2022,3, e160.
[10] Xu H.; Cheng P.Aggregate. 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.Luminescence.2021,36, 958-963.
[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, 15349-15353.
[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, 1249-1259.
[14] Chen Y.; Lam J. W. Y.; Kwok R. T. K.; Liu B.; Tang, B. Z.Mater. Horiz.2019,6, 428-433.
[15] Feng X.; Wang X. H.; Redshaw C.; Tang, B. Z.Chem. Soc. Rev.2023,52, 6715-6753.
[16] 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, 133,13349-62.
[17] Islam M. M.; Hu Z.; Wang Q. S.; Redshaw C.; Feng X.Mater. Chem. Front. 2019,3, 762-781.
[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, 3319-3330.
[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, 8503-8514.
[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.small.2021,17, 2103537.
[21] Frisch M. J.; Trucks G. W.; Schlegel H. B.; et al . Gaussian 09, revision A. 08 ; Gaussian, Inc.: Wallingford, CT, 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, 2854-2863.
[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, 13349-13362.
[24] Thomas K. R. J.; Maurya A.; Nagar M. R.; Jou J-H.Dyes. Pigm.2023,216, 111373.
[25] Song X. Y.; Wang M.; Liu W.; Zheng H.; Redshaw C.; Feng X.; Zhao Z. J.; Tang B. Z.Dyes. Pigm.2023, 219,111532.
[26] Ha, J. M.; Hur, S. H.; Pathak, A.; Jeong, J-E.; Woo, H. Y.;NPG. Asia. Materials. 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, 6438-6443.
[29] Zhu H. C.; Huang J. Y.; Kong L.; Tian Y. P.; Yang, J. X.Dyes. Pigm.2018,51, 140-148.
[30] Mataga N., Kaifu Y., Koizumi M.Bull. Chem.Soc. Jpn,1956,29,465-470.
[31] E. Lippert, Ber. Bunsenges.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. Sinica.2022,80, 282—290.
[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, 7901-7910.
[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, 1681-1691.

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jidong Zhang, Yao Yang, Jie Zhang, Wei She. Detection of Zn(II) by Tetraphenylethyene Fluorescent Probe Based on Aggregation-Induced Emission (AIE)-Excited State Intramolecular Proton Transfer (ESIPT) Effect [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1337-1342.
[2]	Yang Zhao, Panpan Chen, Lizhi Han, Enju Wang. Aggregation-Induced Emission and Cell Imaging of Triphenylimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2454-2461.
[3]	Ling Liu, Taotao Hao, Wanhua Wu, Cheng Yang. Stilbene-Based Molecular Switches with Aggregation Induced Emission (AIE) Function Constructed by Supramolecular Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2189-2196.
[4]	Yuehua Zhang, Fei Nie, Lu Zhou, Xiaofeng Wang, Yuan Liu, Yanping Huo, Wencheng Chen, Zujin Zhao. Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3876-3887.
[5]	Yangyang Li, Xiaofei Sun, Xiaoling Hu, Yuanyuan Ren, Keli Zhong, Xiaomei Yan, Lijun Tang. Synthesis of Triphenylamine Derivative and Its Recognition for Hg²⁺ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 320-325.
[6]	Jidong Zhang, Wanlin Yan, Wenqiang Hu, Dian Guo, Dalong Zhang, Xiaoxin Quan, Xianpan Bu, Siyu Chen. Design and Synthesis of a Zn²⁺ Fluorescent Probe Based on Aggregation Induced Luminescence Properties [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 326-331.
[7]	Meng Liu, Yanru Huang, Xiaofei Sun, Lijun Tang. An “Aggregation-Induced Emission+Excited-State Intramolecular Proton Transfer” Mechanisms-Based Benzothiazole Derived Fluorescent Probe and Its ClO^–Recognition [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 345-351.
[8]	Weikang Xia, Chuang Liu, Sheng Ye, Lei Wang, Ruiyuan Liu. Synthesis of A Sulfonamide-Substituted Benzothiadiazole-Based Fluorescent Dye and Study of Its Application for Long-Term Cancer Cell Tracking [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2535-2541.
[9]	Zhaohua Chen, Xiying Cao, Sihong Chen, Shiwei Yu, Yanlan Lin, Shuting Lin, Zhaoyang Wang. Design, Synthesis and Application of Trisubstituted Olefinic Aggregation-Induced Emission Molecules [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2355-2363.
[10]	Ze Guo, Di Wu, Lili Wang, Zheng Duan. BF₃•Et₂O Promoted Dienone-Phenol Type Rearrangement to Synthesize Phosphepine with Aggregation Induced Luminescence (AIE) Effect [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2481-2487.
[11]	Yuetian Guo, Yongxin Pan, Lijun Tang. Progresses in Reactive Fluorescent Probes with Fused Aggregation- Induced Emission (AIE) and Excited State Intramolecular Proton Transfer (ESIPT) Structures [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1640-1650.
[12]	Yongmei Zhao, Yeshu Mu, Wen Luo, Zhiyong Tian. Synthesis of Naphthalimide Derivatives as Cholinesterase Inhibitors with Aggregation Induced Emission Properties [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 819-829.
[13]	Wei Ding, Bowen Cheng, Meng Wang, Qingyu Dou, Siying Li, Peng Zhang, Qianfu Luo. Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 363-383.
[14]	Jiamin Tan, Yajun Yu, Meng Guan, Yunhui Zhao, Zilong Tang, Zhihua Zhou, Tao Guo. Design and Synthesis of Novel Aggregation-Induced Luminescence Molecules Based on Isoquinoline [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3776-3783.
[15]	Yunle Lu, Yanjie Wang, Liangliang Zhu, Bingbing Yue. Progress in Synthesis and Aggregation-Induced Phosphorescence of Persulfurated Arene Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3549-3561.