Abstract
Two cationic heteroleptic four-coordinate Cu(I) complexes were successfully synthesized and characterized by 1H NMR, 13C NMR, 31P NMR spectroscopy and mass spectrometry. The crystal structures of the complexes have been determined by single-crystal X-ray diffraction. UV/Visible absorption spectra of these complexes show ligand-centered π-π* and charge transfer transitions. In the solid state the complexes show intense emissions with microsecond-scale lifetime and relatively high efficiency at room temperature. The photophysical behavior at T = 298 and 77 K indicates that the emissions of these complexes are thermally activated delayed fluorescence mixed with phosphorescence.
Acknowledgments
We thank Jiange Wang for the single-crystal structure determinations.
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Research ethics: Not applicable.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Competing interests: The authors declare no conflict of interest regarding this article.
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Research funding: None declared.
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Data availability: The raw data can be obtained on request from the corresponding author.
References
1. Pashaei, B., Karimi, S., Shahroosvand, H., Abbasi, P., Pilkington, M., Bartolotta, A., Fresta, E., Fernandez-Cestau, J., Costa, R. D., Bonaccorso, F. Chem. Soc. Rev. 2019, 48, 5033–5139; https://doi.org/10.1039/c8cs00075a.Search in Google Scholar PubMed
2. Li, G., Zhu, D., Wang, X., Su, Z., Bryce, M. R. Chem. Soc. Rev. 2020, 49, 765–838.10.1039/C8CS00660ASearch in Google Scholar PubMed
3. Amouri, H. Chem. Rev. 2023, 123, 230–270; https://doi.org/10.1021/acs.chemrev.2c00206.Search in Google Scholar PubMed
4. Lu, G., Wu, R., Li, N., Wang, X., Zhou, L., Yang, C. J. Mater. Chem. C 2022, 10, 17303–17308.10.1039/D2TC02808ESearch in Google Scholar
5. Li, W., Miao, T., Wang, B., Liu, J., Lü, X., Fu, G., Feng, W., Wong, W.-Y. J. Mater. Chem. C 2021, 9, 8337–8344; https://doi.org/10.1039/d1tc01977e.Search in Google Scholar
6. Ma, H., Shen, K., Wu, Y., Xia, F., Yu, F., Sun, Z., Qian, C., Peng, Q., Zhang, H.-H., You, C., Xie, G., Hang, X.-C., Huang, W. Mater. Chem. Front. 2019, 3, 2448–2454; https://doi.org/10.1039/c9qm00347a.Search in Google Scholar
7. Chen, Y., Qian, C., Qin, K., Li, H., Shi, X., Lu, Z., Ma, H., Qin, T., Hang, X.-C., Huang, W. ACS Appl. Mater. Interfaces 2021, 13, 52833–52839; https://doi.org/10.1021/acsami.1c13843.Search in Google Scholar PubMed
8. Shafikov, M. Z., Daniels, R., Kozhevnikov, V. N. J. Phys. Chem. Lett. 2019, 10, 7015–7024; https://doi.org/10.1021/acs.jpclett.9b03002.Search in Google Scholar PubMed
9. Zhang, M., Zhang, S.-W., Wu, C., Li, W., Wu, Y., Yang, C., Meng, Z., Xu, W., Tang, M.-C., Xie, R., Meng, H., Wei, G. ACS Appl. Mater. Interfaces 2022, 14, 1546–1556; https://doi.org/10.1021/acsami.1c19127.Search in Google Scholar PubMed
10. Li, G., Zhao, X., Fleetham, T., Chen, Q., Zhan, F., Zheng, J., Yang, Y.-F., Lou, W., Yang, Y., Fang, K., Shao, Z., Zhang, Q., She, Y. Chem. Mater. 2020, 32, 537–548; https://doi.org/10.1021/acs.chemmater.9b04263.Search in Google Scholar
11. Sun, Y., Chen, C., Liu, B., Guo, Y., Feng, Z., Zhou, G., Chen, Z., Yang, X. J. Mater. Chem. C 2021, 9, 5373–5378; https://doi.org/10.1039/d0tc05965j.Search in Google Scholar
12. Li, X., Zang, C.-X., Gao, Y., Wen, L.-L., Shao, K.-Z., Ding, G.-Y., Shan, G.-G., Xie, W.-F., Su, Z.-M. Inorg. Chem. 2022, 61, 20299–20307; https://doi.org/10.1021/acs.inorgchem.2c02702.Search in Google Scholar PubMed
13. Park, H. J., Jang, J.-H., Lee, J.-H., Hwang, D.-H. ACS Appl. Mater. Interfaces 2022, 14, 34901–34908; https://doi.org/10.1021/acsami.2c06891.Search in Google Scholar PubMed
14. Kim, S.-Y., Kim, J.-H., Lee, S., Yun, B.-S., Son, H.-J., Kang, S. O. Inorg. Chem. 2022, 61, 18554–18567; https://doi.org/10.1021/acs.inorgchem.2c02890.Search in Google Scholar PubMed
15. Zhu, L., Sha, C., Lv, A., Xie, W., Shen, K., Chen, Y., Xie, G., Ma, H., Li, H., Hang, X.-C. Inorg. Chem. 2022, 61, 10402–10409; https://doi.org/10.1021/acs.inorgchem.2c01063.Search in Google Scholar PubMed
16. Liao, X.-J., Zhu, J.-J., Yuan, L., Yan, Z.-P., Luo, X.-F., Zhang, Y.-P., Lu, J.-J., Zheng, Y.-X. J. Mater. Chem. C 2021, 9, 8226–8232, https://doi.org/10.1039/d1tc01449h.Search in Google Scholar
17. Shen, Y., Kong, X., Yang, F., Bian, H.-D., Cheng, G., Cook, T. R., Zhang, Y. Inorg. Chem. 2022, 61, 16707–16717; https://doi.org/10.1021/acs.inorgchem.2c02467.Search in Google Scholar PubMed
18. Ou, C., Qiu, Y.-C., Cao, C., Zhang, H., Qin, J., Tu, Z.-L., Shi, J., Wu, Z.-G. Inorg. Chem. Front. 2023, 10, 1018–1026, https://doi.org/10.1039/d2qi02261c.Search in Google Scholar
19. Barman, D., Narang, K., Gogoi, R., Barman, D., Lyer, P. K. J. Mater. Chem. C 2022, 10, 8536–8583.10.1039/D1TC05906HSearch in Google Scholar
20. Shi, Y.-Z., Wu, H., Wang, K., Yu, J., Ou, X.-M., Zhang, X.-H. Chem. Sci. 2022, 13, 3625–3651.10.1039/D1SC07180GSearch in Google Scholar PubMed PubMed Central
21. Zhou, Z., Xie, X., Sun, Z., Wang, X., An, Z., Huang, W. J. Mater. Chem. C 2023, 11, 3143–3161; https://doi.org/10.1039/d2tc05256c.Search in Google Scholar
22. Chen, L., Chen, W.-C., Yang, Z., Tan, J.-H., Ji, S., Zhang, H.-L., Huo, Y., Lee, C.-S. J. Mater. Chem. C 2021, 9, 17233–17264, https://doi.org/10.1039/d1tc04184c.Search in Google Scholar
23. Li, Q., Wang, J., Wu, Y., Zhao, F., He, H., Wang, Y. Polyhedron 2022, 218, 115785; https://doi.org/10.1016/j.poly.2022.115785.Search in Google Scholar
24. Olaru, M., Rychagova, E., Ketkov, S., Hynkarenko, Y., Yakunin, S., Kovalenko, M. V., Yablonskiy, A., Andreev, B., Kleemiss, F., Beckmann, J., Vogt, M. J. Am. Chem. Soc. 2020, 142, 373–381; https://doi.org/10.1021/jacs.9b10829.Search in Google Scholar PubMed
25. Xu, K., Chen, B.-L., Yang, F., Liu, L., Zhong, X.-X., Wang, L., Zhu, X.-J., Li, F.-B., Wong, W.-Y., Qin, H.-M. Inorg. Chem. 2021, 60, 4841–4851; https://doi.org/10.1021/acs.inorgchem.0c03755.Search in Google Scholar PubMed
26. Yu, P., Peng, D., He, L.-H., Chen, J.-L., Wang, J.-Y., Liu, S.-J., Wen, H.-R. Inorg. Chem. 2022, 61, 254–264; https://doi.org/10.1021/acs.inorgchem.1c02807.Search in Google Scholar PubMed
27. Farias, G., Salla, C. A. M., Heying, R. S., Bortoluzzi, A. J., Curcio, S. F., Cazati, T., dos Santos, P. L., Monkman, A. P., de Souza, B., Bechtold, I. H. J. Mater. Chem. C 2020, 8, 14595–14604; https://doi.org/10.1039/d0tc03660a.Search in Google Scholar
28. Meyer, M., Mardegan, L., Tordera, D., Prescimone, A., Sessolo, M., Bolink, H. J., Constable, E. C., Housecroft, C. E. Dalton Trans. 2021, 50, 17920–17934; https://doi.org/10.1039/d1dt03239a.Search in Google Scholar PubMed PubMed Central
29. Huang, C.-H., Yang, M., Chen, X.-L., Lu, C.-Z. Dalton Trans. 2021, 50, 5171–5176; https://doi.org/10.1039/d0dt04424e.Search in Google Scholar PubMed
30. He, T.-F., Ren, A.-M., Chen, Y.-N., Hao, X.-L., Shen, L., Zhang, B.-H., Wu, T.-S., Zhang, H.-X., Zou, L.-Y. Inorg. Chem. 2020, 59, 12039–12053; https://doi.org/10.1021/acs.inorgchem.0c00980.Search in Google Scholar PubMed
31. Yamazaki, Y., Tsukuda, T., Furukawa, S., Dairiki, A., Sawamura, S., Tsubomura, T. Inorg. Chem. 2020, 59, 12375–12384; https://doi.org/10.1021/acs.inorgchem.0c01445.Search in Google Scholar PubMed
32. Housecroft, C. E., Constable, E. C. J. Mater. Chem. C 2022, 10, 4456–4482; https://doi.org/10.1039/d1tc04028f.Search in Google Scholar PubMed PubMed Central
33. Sandoval-Pauker, C., Santander-Nelli, M., Dreyse, P. RSC Adv. 2022, 12, 10653–10674; https://doi.org/10.1039/d1ra08082b.Search in Google Scholar PubMed PubMed Central
34. Li, C., Mackenzie, C. F. R., Said, S. A., Pal, A. K., Haghighatbin, M. A., Babaei, A., Sessolo, M., Cordes, D. B., Slawin, A. M. Z., Kamer, P. C. J., Bolink, H. J., Hogan, C. F., Zysman-Colman E. Inorg. Chem. 2021, 60, 10323–10339; https://doi.org/10.1021/acs.inorgchem.1c00804.Search in Google Scholar PubMed
35. Klein, M., Rau, N., Wende, M., Sundermeyer, J., Cheng, G., Che, C.-M., Schinabeck, A., Yersin, H. Chem. Mater. 2020, 32, 10365–10382; https://doi.org/10.1021/acs.chemmater.0c02683.Search in Google Scholar
36. Li, X., Zhang, J., Zhao, Z., Yu, X., Li, P., Yao, Y., Liu, Z., Jin, Q., Bian, Z., Lu, Z., Huang, C. ACS Appl. Mater. Interfaces 2019, 11, 3262–3270; https://doi.org/10.1021/acsami.8b15897.Search in Google Scholar PubMed
37. Wang, Z., Zheng, C., Wang, W., Xu, C., Ji, B., Zhang, X. Inorg. Chem. 2016, 55, 2157–2164; https://doi.org/10.1021/acs.inorgchem.5b02546.Search in Google Scholar PubMed
38. Wang, Z., Sun, X., Fu, W., Xu, C., Ji, B. J. Lumin. 2018, 204, 618–625; https://doi.org/10.1016/j.jlumin.2018.08.064.Search in Google Scholar
39. Wang, Z., Sun, X., Xu, C., Ji, B. Front. Chem. 2019, 7, 422; https://doi.org/10.3389/fchem.2019.00422.Search in Google Scholar PubMed PubMed Central
40. Lou, X., Tian, Y., Wang, Z. Z. Naturforsch. 2022, 77b, 673–679.10.1515/znb-2022-0092Search in Google Scholar
41. Cai, X., Ma, T., Ding, D., Wang, Z., Li, M., Chen, S., Ma, Z., Teng, S., Du, Y., Zhang, T., Xu, C. Z. Anorg. Allg. Chem. 2021, 647, 1277–1283; https://doi.org/10.1002/zaac.202000470.Search in Google Scholar
42. Frisch, M. J., 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, J. A.Jr., 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 D.01); Gaussian, Inc.: Wallingford CT (USA), 2013.Search in Google Scholar
43. Sheldrick, G. M. Sadabs, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen (Germany), 1994.Search in Google Scholar
44. Sheldrick, G. M. Shelxs-97, Program for the Solution of Crystal Structures; University of Göttingen: Göttingen (Germany), 1997.Search in Google Scholar
45. Sheldrick, G. M. Shelxl-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen (Germany), 1997.Search in Google Scholar
46. Armaroli, N. Chem. Soc. Rev. 2001, 30, 113–124; https://doi.org/10.1039/b000703j.Search in Google Scholar
47. Lin, L., Chen, D.-H., Yu, R., Chen, X.-L., Zhu, W.-J., Liang, D., Chang, J.-F., Zhang, Q., Lu, C.-Z. J. Mater. Chem. C 2017, 5, 4495–4504; https://doi.org/10.1039/c7tc00443e.Search in Google Scholar
48. Leitl, M. J., Krylova, V. A., Djurovich, P. I., Thompson, M. E., Yersin, H. J. Am. Chem. Soc. 2014, 136, 16032–16038; https://doi.org/10.1021/ja508155x.Search in Google Scholar PubMed
49. Hofbeck, T., Monkowius, U., Yersin, H. J. Am. Chem. Soc. 2015, 137, 399–404; https://doi.org/10.1021/ja5109672.Search in Google Scholar PubMed
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