Citation: Shuqi Chen, Cankun Zhang, Xiaonuo Dong, Hui-Jun Zhang, Jianbin Lin. Synthesis and photophysical properties of alternating donor-acceptor conjugated nanorings[J]. Chinese Chemical Letters, ;2025, 36(6): 110354. doi: 10.1016/j.cclet.2024.110354 shu

Synthesis and photophysical properties of alternating donor-acceptor conjugated nanorings

a.
Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, Xiamen University, Xiamen 361005, China
b.
Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM), Xiamen University, Xiamen 361005, China

jb.lin@xmu.edu.cn

Received Date: 23 May 2024
Revised Date: 8 August 2024
Accepted Date: 21 August 2024
Available Online: 23 August 2024

Figures(5)

Herein, we report the design and synthesis of alternating donor-acceptor nanorings [3]C-NA and [4]C-NA, along with a reference linear molecule [3]L-NA, via electrochemical oxidation-induced reductive elimination of alkynyl platinum(Ⅱ) complexes. Unlike [3]L-NA, which exhibits charge defects at its end-groups, the cyclic structures of [3]C-NA and [4]C-NA facilitate enhanced electron delocalization, enabling efficient charge transfer in low-polarity toluene. In the polar solvent dichloromethane (DCM), the increased flexibility of [4]C-NA promotes intramolecular charge transfer and suppresses charge recombination. The observed faster intramolecular charge transfer and slower charge recombination rates in these nanoring acceptor materials suggest their potential for improving the power conversion efficiency of organic solar cells, providing valuable insights for the design of nanoring acceptor materials.
- Nanorings,
- Donor-acceptor,
- Intramolecular charge transfer,
- Femtosecond transient absorption
1. [1]
  B. Zhang, R. Hernández Sánchez, Y. Zhong, et al., Nat. Commun. 9 (2018) 1957. doi: 10.1038/s41467-018-04246-0
2. [2]
  M. Ball, B. Zhang, Y. Zhong, et al., Acc. Chem. Res. 52 (2019) 1068-1078. doi: 10.1021/acs.accounts.9b00017
3. [3]
  E.J. Leonhardt, R. Jasti, Nat. Rev. Chem. 3 (2019) 672-686. doi: 10.1038/s41570-019-0140-0
4. [4]
  Y. Li, H. Kono, T. Maekawa, et al., Acc. Mater. Res. 2 (2021) 681-691. doi: 10.1021/accountsmr.1c00105
5. [5]
  H. Cong, Y. Luan, Synlett 28 (2017) 1383-1388. doi: 10.1055/s-0036-1588978
6. [6]
  S. Zhong, L. Zhu, S. Wu, et al., Chin. Chem. Lett. 34 (2023) 108124. doi: 10.1016/j.cclet.2022.108124
7. [7]
  H. Zhang, J. Lin, Chin. J. Org. Chem. 42 (2022) 3437-3455. doi: 10.6023/cjoc202205006
8. [8]
  M.L. Ball, B. Zhang, Q. Xu, et al., J. Am. Chem. Soc. 140 (2018) 10135-10139. doi: 10.1021/jacs.8b06565
9. [9]
  E.R. Darzi, R. Jasti, Chem. Soc. Rev. 44 (2015) 6401-6410. doi: 10.1039/C5CS00143A
10. [10]
  M. Rickhaus, A. Vargas Jentzsch, L. Tejerina, et al., J. Am. Chem. Soc. 139 (2017) 16502-16505. doi: 10.1021/jacs.7b10710
11. [11]
  K. Miki, K. Ohe, Chem. Eur. J. 26(12) (2019) 2529-2575.
12. [12]
  A. Vyšniauskas, M. Qurashi, N. Gallop, et al., Chem. Sci. 6 (2015) 5773-5778. doi: 10.1039/C5SC02248G
13. [13]
  P. Liu, Y. Hisamune, M.D. Peeks, et al., Angew. Chem. Int. Ed. 55 (2016) 8358-8362. doi: 10.1002/anie.201602909
14. [14]
  A. Nowak-Król, K. Shoyama, M. Stolte, et al., Chem. Commun. 54 (2018) 13763-13772. doi: 10.1039/c8cc07640e
15. [15]
  Q. Wu, D. Deng, K. Lu, et al., Chin. Chem. Lett. 28 (2017) 2065-2077. doi: 10.1016/j.cclet.2017.08.046
16. [16]
  D. Jia, H. Zhong, S. Jiang, et al., Chin. Chem. Lett. 33 (2022) 4900-4903. doi: 10.1016/j.cclet.2022.02.081
17. [17]
  M. Ball, Y. Zhong, B. Fowler, et al., J. Am. Chem. Soc. 138 (2016) 12861-12867. doi: 10.1021/jacs.6b05474
18. [18]
  T. Kawase, H.R. Darabi, M. Oda, Angew. Chem. Int. Ed. 35 (1996) 2664-2666. doi: 10.1002/anie.199626641
19. [19]
  K. Miki, T. Matsushita, Y. Inoue, et al., Chem. Commun. 49 (2013) 9092-9094. doi: 10.1039/c3cc42561d
20. [20]
  S. Lee, E. Chénard, D.L. Gray, et al., J. Am. Chem. Soc. 138 (2016) 13814-13817. doi: 10.1021/jacs.6b08752
21. [21]
  T.A. Schaub, J.T. Margraf, L. Zakharov, et al., Angew. Chem. Int. Ed. 57 (2018) 16348-16353. doi: 10.1002/anie.201808611
22. [22]
  L. Zhao, B.H. Northrop, P. Stang, J, J. Am. Chem. Soc. 130 (2008) 11886-11888. doi: 10.1021/ja805770w
23. [23]
  G. Fuhrmann, T. Debaerdemaeker, P. Bäuerle, Chem. Commun. 38 (2003) 948-949.
24. [24]
  E. Kayahara, T. Iwamoto, T. Suzuki, et al., Chem. Lett. 42 (2013) 621-623. doi: 10.1246/cl.130188
25. [25]
  L. Zhang, G. Zhang, H. Qu, et al., Angew. Chem. Int. Ed. 60 (2021) 24543-24548. doi: 10.1002/anie.202107893
26. [26]
  F. Su, Y. Hong, G. Zhang, et al., Chem. Sci. 15 (2024) 5604-5611. doi: 10.1039/d4sc00195h
27. [27]
  Z. Sun, T. Suenaga, P. Sarkar, et al., Proc. Natl. Acad. Sci. U.S.A. 113 (2016) 8109-8114. doi: 10.1073/pnas.1606530113
28. [28]
  Y. Wang, Z. He, G. Chen, et al., Chin. Chem. Lett. 28 (2017) 2133-2138. doi: 10.1016/j.cclet.2017.09.054
29. [29]
  S.K. Keshri, A. Takai, T. Ishizuka, et al., Angew. Chem. Int. Ed. 59 (2020) 5254-5258. doi: 10.1002/anie.201914414
30. [30]
  C. Reichardt, Chem. Rev. 94 (1994) 2319-2358. doi: 10.1021/cr00032a005
31. [31]
  T. Kuwabara, J. Orii, Y. Segawa, et al., Angew. Chem. Int. Ed. 54 (2015) 9646-9649. doi: 10.1002/anie.201503397
32. [32]
  S. Nishigaki, M. Fukui, H. Sugiyama, et al., Chem. Eur. J. 23 (2017) 7227-7231. doi: 10.1002/chem.201701547
33. [33]
  X. Chen, J. Hu, J. Lin, et al., Chin. Chem. Lett. 36 (2025) 109923 doi: 10.1016/j.cclet.2024.109923
34. [34]
  Z. Kuang, G. He, H. Song, et al., J. Phys. Chem. C 122 (2018) 3727-3737. doi: 10.1021/acs.jpcc.7b11411
35. [35]
  S. Izumi, H.F. Higginbotham, A. Nyga, et al., J. Am. Chem. Soc. 142 (2020) 1482-1491. doi: 10.1021/jacs.9b11578
36. [36]
  S. Gámez-Valenzuela, I. Torres-Moya, A. Sánchez, et al., Chem. Eur. J. 29 (2023) e202301639. doi: 10.1002/chem.202301639
37. [37]
  J. Jiang, A. Alsam, S. Wang, et al., J. Phys. Chem. A 121 (2017) 4891-4901. doi: 10.1021/acs.jpca.7b03547
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1.
沈阳化工大学材料科学与工程学院沈阳 110142