Chinese Journal of Organic Chemistry >
Design and Synthesis of Thermal Delayed Fluorescence (TADF) Photocatalyst and Its Photocatalytic Dehalogenation Performance
Received date: 2022-11-11
Revised date: 2023-01-25
Online published: 2023-03-24
Supported by
National Natural Science Foundation of China(21376222); Natural Science Foundation of Zhejiang Province(LY18B060011)
In order to improve the photocatalytic efficiency, a kind of thermal delayed fluorescence (TADF) photocatalyst of tricarbazolyl phthalonitrile was designed and synthesized. A system for the dehalogenation of aryl halohydrocarbons was established, using TADF material as photocatalyst and disulfide as hydrogen transfer catalyst. Different organic halides (including C—Br bonds and C—Cl bonds) can be dehalogenated with moderate to excellent yields. Compared with 2,4,5,6-tetrakis- (carbazol-9-yl)-1,3-dicyanobenzene (4CzIPN), the representative thermal delayed fluorescent material, 4-(N,N-dimethylami- no)-3,5,6-tri(9-carbazolyl)phthalonitrile (3CzDMAPN) has higher catalytic efficiency and specificity.
Key words： photocatalysis; dehalogenation
Yaxin Liu , Yu Zhang , Shuping Luo . Design and Synthesis of Thermal Delayed Fluorescence (TADF) Photocatalyst and Its Photocatalytic Dehalogenation Performance[J]. Chinese Journal of Organic Chemistry, 2023 , 43(7) : 2476 -2483 . DOI: 10.6023/cjoc202211015
| [1] | Zeghioud, H.; Khellaf, N.; Djelal, H.; Amrane, A. Chem. Eng. Commun. 2016, 203, 1415. |
| [2] | Atashgahi, S.; H?ggblom, M. M.; Smidt, H. Environ. Microbiol. 2018, 20, 934. |
| [3] | Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009. |
| [4] | Harrad, S.; Robson, M.; Hazrati, S.; Hazrati, S.; Baxter-Plant, V.; Deplanche, K.; Redwood, M.; Macaskie, L. J. Environ. Monit. 2007, 9, 314. |
| [5] | Shen, Y. F.; Zhao, R.; Wang, J. F.; Chen, X. X.; Ge, X. L.; Chen, M. D. Waste Manage. 2016, 49, 287. |
| [6] | Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739. |
| [7] | Szostak, M.; Spain, M.; Procter, D. J. Chem. Soc. Rev. 2013, 42, 9155. |
| [8] | Liu, W.; Hou, F. Y. Tetrahedron 2017, 73, 931. |
| [9] | Zheng, H. X.; Shan, X. H.; Qu, J. P.; Kang, Y. B. Org. Lett. 2017, 19, 5114. |
| [10] | Dewanji, A.; Mück-Lichtenfeld, C.; Studer, A. Angew. Chem., Int. Ed. 2016, 55, 6749. |
| [11] | Bhattacharjya, A.; Klumphu, P.; Lipshutz, B. H. Org. Lett. 2015, 17, 1122. |
| [12] | Pyo, A.; Kim, S.; Kumar, M. R.; Byeun, A.; Eom, M. S.; Han, M. S.; Lee, S. Tetrahedron Lett. 2013, 54, 5207. |
| [13] | Suzuka, T.; Sueyoshi, H.; Maehara, S.; Ogasawara, H. Molecules 2015, 20, 9906. |
| [14] | Isley, N. A.; Hageman, M. S.; Lipshutz, B. H. Green Chem. 2015, 17, 893. |
| [15] | Hekmatshoar, R.; Sajadi, S.; Heravi, M. M. J. Chin. Chem. Soc. 2008, 55, 616. |
| [16] | Fincker, M.; Spormann, A. M. Annu. Rev. Biochem. 2017, 86, 357. |
| [17] | Padilla-Crespo, E.; Yan, J.; Swift, C.; Wagner, D.; Chourey, K.; Hettich, R.; Ritalahti, K.; L?ffler, F. Appl. Environ. Microbiol. 2014, 80, 808. |
| [18] | Payne, K. A. P.; Quezada, C. P.; Fisher, K.; Dunstan, M. S.; Collins, F. A.; Sjuts, H.; Levy, C.; Hay, S.; Rigby, S. E. J.; Leys, D. Nature 2015, 517, 513. |
| [19] | Michelet, B.; Deldaele, C. Org. Lett. 2017, 19, 3576. |
| [20] | Devery, J. J.; Nguyen, J. D.; Dai, C. H.; Stephenson, C. R. J. ACS Catal. 2016, 6, 5962. |
| [21] | Kim, H.; Lee, C. Angew. Chem., Int. Ed. 2012, 51, 12303. |
| [22] | Fukuyama, T.; Fujita, Y.; Miyoshi, H.; Ryu, I.; Kao, S.; Wu, Y. Chem. Commun. 2018, 54, 5582. |
| [23] | Cao, D. W.; Yan, C. X.; Zhou, P. P.; Zeng, H. Y.; Li, C. J. Chem. Commun. 2019, 55, 767. |
| [24] | Yuan, T.; Zheng, M. F.; Markus, A.; Wang, X. C. Chem. Sci. 2021, 12, 6323. |
| [25] | McCarthy, B. G.; Pearson, R. M.; Lim, C.-H.; Stator, S. M.; Damrauer, N. H.; Miyake, G. M. J. Am. Chem. Soc. 2018, 140, 5088. |
| [26] | Noto, N.; Koike, T.; Akita, M. ACS Catal. 2019, 9, 4382. |
| [27] | Boyington, A. J.; Seath, C. P.; Zearfoss, A. M.; Xu, Z. H.; Jui, N. J. Am. Chem. Soc. 2019, 141, 4147. |
| [28] | Li, Y. J.; Ye, Z. Q.; Lin, Y. M.; Liu, Y.; Zhang, Y. M. Gong, L. Nat. Commun. 2021, 12, 2894. |
| [29] | Niu, T. F.; Chen, S. J.; Hong, M.; Zhang, T. H.; Chen, J. Y.; Dong, X. Y.; Ni, B. Q. Green Chem. 2020, 22, 5042. |
| [30] | Kiyoshi, T.; Rohand, T. Tetrahedron Lett. 2020, 61, 152467. |
| [31] | Madduluri, V. K.; Baig, N.; Chander, S.; Murugesan, S.; Sah, A. K. Catal. Commun. 2020, 137, 105931. |
| [32] | Akiyama, T.; Taniguchi, T.; Saito, N.; Doi, R.; Honma, T.; Tamenori, Y.; Ohki, Y.; Takahashi, N.; Fujioka, H.; Sato, Y.; Arisawa, M. Green Chem. 2017, 19, 3357. |
| [33] | Liu, Q.; Liu, Y. X.; Song, H. J.; Song, H. J.; Wang, Q. M. Adv. Synth. Catal. 2020, 362, 3110. |
| [34] | Chiou, C. T.; Schmedding, D. W.; Manes, M. Environ. Sci. Technol. 2005, 39, 8840. |
| [35] | Abdine, R. A. A.; Kurpik, G.; Walczak, A.; Aeash, S. A. A.; Stefankiewicz, A. R.; Monnier, F.; Taillefer, M. J. Catal. 2019, 376, 119. |
| [36] | Ameen, D.; Snape, T. J. Tetrahedron Lett. 2015, 56, 1816. |
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