Chinese Journal of Organic Chemistry >
Photoinduced Room-Temperature Phosphorescence of Triphenylamine-Phenothiazine Derivative-Doped Polymers
Received date: 2024-04-10
Revised date: 2024-06-23
Online published: 2024-07-10
Supported by
National Natural Science Foundation of China(22305172); China Postdoctoral Science Foundation(2023M732586); China Postdoctoral Science Foundation(2024T170640); Postdoctoral Fellowship Program of China Postdoctoral Science Foundation (CPSF)(GZB20230509)
Photo-responsive room-temperature phosphorescent (RTP) materials have garnered significant interest due to the advantages of rapid response, spatiotemporal control, and contactless precision manipulation. However, the development of such materials remains in its infancy, underscoring the importance of exploiting novel and efficient light-responsive RTP molecules. In this work, three phenothiazine derivatives of TPA-PTZ, TPA-2PTZ, and TPA-3PTZ were successfully synthesized via the Buchwald-Hartwig C—N coupling reaction. By embedding these molecules as RTP guests into polymethyl methacrylate (PMMA) matrix, photo-induced RTP properties were realized. Upon sustained UV irradiation, there was an enhancement of 19 times in the quantum yield to reach a value of 5.68%. Remarkably, these materials exhibit superior alongside robust light and thermal stability, maintaining high phosphorescence intensity even after prolonged UV exposure (irradiation for>200 s by a 365 nm UV lamp with the power of 500 µW•cm-2) or at higher temperature up to 75 ℃. The outstanding properties of these photo-induced RTP materials make them promising candidates for applications in information encryption, anti-counterfeiting, and advanced optical materials.
Nan Li , Yunsheng Wang , Zhen Li . Photoinduced Room-Temperature Phosphorescence of Triphenylamine-Phenothiazine Derivative-Doped Polymers[J]. Chinese Journal of Organic Chemistry, 2024 , 44(8) : 2487 -2494 . DOI: 10.6023/cjoc202404016
| [1] | Li, D.; Lu, F.; Wang, J.; Hu, W.; Cao, X. M.; Ma, X.; Tian, H. J. Am. Chem. So.. 2018, 140, 1916. |
| [2] | Gmelch, M.; Thomas, H.; Fries, F.; Reineke, S. Sci. Ad.. 2019, 5, eaau7310. |
| [3] | Zhang, Z. Y.; Liu, Y. Chem. Sc.. 2019, 10, 7773. |
| [4] | Kabe, R.; Notsuka, N.; Yoshida, K.; Adachi, C. Adv. Mate.. 2016, 28, 655. |
| [5] | Zhang, G.; Palmer, G. M.; Dewhirst, M. W.; Fraser, C. L. Nat. Mate.. 2009, 8, 747; |
| [6] | Fan, Y.; Li, Q.; Li, Z. Sci. China Chem. 2023, 66, 2930. |
| [7] | Wang, J.; Huang, Z.; Ma, X.; Tian, H. Angew. Chem., Int. Ed. 2020, 59, 9928. |
| [8] | Baryshnikov, G.; Minaev, B.; Agren, H. Chem. Re.. 2017, 117, 6500. |
| [9] | Li, Y.; Gecevicius, M.; Qiu, J. Chem. Soc. Re.. 2016, 45, 2090. |
| [10] | Yang, Y.; Li, A.; Yang, Y.; Wang, J.; Chen, Y.; Yang, K.; Tang, B. Z.; Li, Z. Angew. Chem., Int. Ed. 2023, 62, e2023088. |
| [11] | Hamzehpoor, E.; Ruchlin, C.; Tao, Y.; Liu, C-H.; Titi, H. M.; Perepichka, D. F. Nat. Che.. 2023, 15, 83. |
| [12] | El-Sayed, M. A. J. Chem. Phy.. 1963, 38, 2834. |
| [13] | Yu, Z.; Wu, Y.; Xiao, L.; Chen, J.; Liao, Q.; Yao, J.; Fu, H. J. Am. Chem. So.. 2017, 139, 6376; |
| [14] | Lu, Y.; Wang, Y. ; Zhu, L.; Yue, B. Chin. J. Org. Chem. 2022, 42, 3549 (in Chinese). |
| [14] | (路云乐, 王彦杰, 朱亮亮, 岳兵兵, 有机化学, 2022, 42, 3549.) |
| [15] | Zhang, T.; Ma, X.; Tian, H. Chem. Sc.. 2020, 11, 482. |
| [16] | Tanaka, H.; Shizu, K.; Nakanotani, H.; Adachi, C. J. Mater. Chem. C 2014, 118, 15985. |
| [17] | Chen, C.; Huang, R.; Batsanov, A. S.; Pander, P.; Hsu, Y. T.; Chi, Z.; Dias, F. B.; Bryce, M. R. Angew. Chem., Int. Ed. 2018, 57, 16407. |
| [18] | Wang, Y.; Yang, J.; Fang, M.; Gong, Y.; Ren, J.; Tu, L.; Tang, B. Z.; Li, Z. Adv. Funct. Mate.. 2021, 31. 2101719. |
| [19] | Hirata, S.; Totani, K.; Zhang, J.; Yamashita, T.; Kaji, H.; Marder, S. R.; Watanabe, T.; Adachi, C. Adv. Funct. Mate.. 2013, 23, 3386. |
| [20] | Qin, C.; Liu, W.; Nie, Y.; Gao, Y.; Miao, J.; Li, T.; Jiang, X. Chin. J. Org. Chem. 2020, 40, 2232 (in Chinese). |
| [20] | (秦成远, 刘威, 聂永, 高迎, 苗金玲, 李天瑞, 蒋绪川, 有机化学, 2020, 40, 2232.) |
| [21] | Redondo, C. S.; Kleine, P.; Roszeitis, K.; Achenbach, T.; Kroll, M.; Thomschke, M.; Reineke, S. J. Phys. Chem. C 2017, 121, 14946. |
| [22] | Xie, Y.; Ge, Y.; Peng, Q.; Li, C.; Li, Q.; Li, Z. Adv. Mate.. 2017, 29, 1606829. |
| [23] | Cheng, Z.; Shi, H.; Ma, H.; Bian, L.; Wu, Q.; Gu, L.; Cai, S.; Wang, X.; Xiong, W. W.; An, Z.; Huang, W. Angew. Chem., Int. Ed. 2018, 57, 678. |
| [24] | Ma, X.; Xu, C.; Wang, J.; Tian, H. Angew. Chem., Int. Ed. 2018, 57, 10854. |
| [25] | Yan, Z.; Zou, L.; Ma, X. Chin. J. Org. Chem. 2020, 40, 1814 (in Chinese). |
| [25] | (严子昂, 邹雷, 马骧, 有机化学, 2020, 40, 1814.) |
| [26] | Zhang, X.; Fu, X.; Dai, G.; Jin, H.; Zhang, X.; Bai, J.; Ma, J.; Ma, Z. Acta Polym. Si.. 2023, 54, 1624 (in Chinese). |
| [26] | (张兴达, 付晓华, 戴光阔, 靳惠雯, 张雪, 白景娟, 马佳欣, 马志勇, 高分子学报, 2023, 54, 1624.) |
| [27] | Gu, L.; Wang, X.; Singh, M.; Shi, H.; Ma, H.; An, Z.; Huang, W. J. Phys. Chem. Let.. 2020, 11, 6191. |
| [28] | Yang, J.; Fang, M.; Li, Z. Acc. Mater. Re.. 2021, 2, 644. |
| [29] | Katsurada, Y.; Hirata, S.; Totani, K.; Watanabe, T.; Vacha, M. Adv. Opt. Mate.. 2015, 3, 1726. |
| [30] | Liu, Y.; Ma, L.; Wang, Q.; Ma, X. Acta Chim. Sinic. 2023, 81, 445 (in Chinese). |
| [30] | (刘懿玮, 马良伟, 王巧纯, 马骧, 化学学报, 2023, 81, 445.) |
| [31] | Tian, Ye.; Si, D.; Gao, S.; Cao, R. Acta Chim. Sinic. 2023, 81, 1129 (in Chinese). |
| [31] | (田野, 司端惠, 高水英, 曹荣, 化学学报, 2023, 81, 1129.) |
| [32] | Morantz, D. J.; Young, R. J. Photoche.. 1978, 9, 274. |
| [33] | Liu, Z.; Tian, Y.; Yang, J.; Li, A.; Wang, Y.; Ren, J.; Fang, M.; Tang, B.; Li, Z. Light: Sci. Appl. 2022, 11, 142. |
/
| 〈 |
|
〉 |