Citation: Wenzhong Zhang, Zirui Yan, Lingcheng Chen, Yi Xiao. Sn-fused perylene diimides: Synthesis, mechanism, and properties[J]. Chinese Chemical Letters, ;2024, 35(10): 109582. doi: 10.1016/j.cclet.2024.109582 shu

Sn-fused perylene diimides: Synthesis, mechanism, and properties

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

lcchen@dlut.edu.cn

xiaoyi@dlut.edu.cn

Received Date: 16 August 2023
Revised Date: 17 January 2024
Accepted Date: 28 January 2024
Available Online: 1 February 2024

Figures(7)

The first example of metal Sn-fused perylene diimides (PDI) derivative (Sn-PDI) was designed, synthesized, and investigated. To obtain this type compound, a simple one-pot synthesis, named stannylative cycloaddition reaction, has been successfully developed via a palladium-based catalyst system. The novel mechanism exhibits that the reaction experiences oxidative addition, Pd-cyclization, stannylation, Pd-Sn-cyclization, and reductive elimination processes successively. This stannylative cycloaddition does realize unique σ-π hyperconjugation effect and therefore significantly influencing on the photophysical, electrochemical and excited state properties. Compared with those of PDI, both of the absorption and fluorescence spectra of Sn-PDI display large red-shifts over 20 nm. The electron energy levels of Sn-PDI have changed with an uncommon regulation. And Sn-PDI gives a considerably raised highest occupied molecular orbital (HOMO) level of -6.00 eV More importantly, the singlet excitons of Sn-PDI could efficiently intersystem cross (ISC) into triplet state with a long lifetime of 17.8 µs, which is far longer than that (4.4 ns) of PDI.
- Functional dyes,
- Perylene diimides,
- Organometallic heterocyclics,
- Hyperconjugation,
- Triplet state
1. [1]
  T.C. Patton, Pigment Handbook, Wiley-Interscience, New York, 1973.
2. [2]
  E.B. Faulkner, R.J. Schwartz, High Performance Pigments, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2009.
3. [3]
  T. Weil, T. Vosch, J. Hofkens, et al., Angew. Chem. Int. Ed. 49 (2010) 9068–9093. doi: 10.1002/anie.200902532
4. [4]
  W. Jiang, Y. Li, Z. Wang, Acc. Chem. Res. 47 (2014) 3135–3147. doi: 10.1021/ar500240e
5. [5]
  D.H. Qu, Q.C. Wang, Q.W. Zhang, et al., Chem. Rev. 115 (2015) 7543–7588. doi: 10.1021/cr5006342
6. [6]
  F. Würthner, C.R. Saha-Möller, B. Fimmel, et al., Chem. Rev. 116 (2016) 962–1052. doi: 10.1021/acs.chemrev.5b00188
7. [7]
  Y. Duan, X. Xu, Y. Li, et al., Chin. Chem. Lett. 28 (2017) 2105–2115. doi: 10.1016/j.cclet.2017.08.025
8. [8]
  Y. Hou, R. Shi, H. Yuan, et al., Chin. Chem. Lett. 34 (2023) 107688. doi: 10.1016/j.cclet.2022.07.031
9. [9]
  S. Zhong, L. Zhu, S. Wu, et al., Chin. Chem. Lett. 34 (2023) 108124. doi: 10.1016/j.cclet.2022.108124
10. [10]
  N. Liang, D. Meng, Z. Wang, Acc. Chem. Res. 54 (2021) 961–975. doi: 10.1021/acs.accounts.0c00677
11. [11]
  V. Sharma, J.D.B. Koenig, G.C. Welch, J. Mater. Chem. A 9 (2021) 6775–6789. doi: 10.1039/D0TA11197J
12. [12]
  Q. Fan, W. Ni, L. Chen, et al., Chin. Chem. Lett. 31 (2020) 2965–2969. doi: 10.1016/j.cclet.2020.06.018
13. [13]
  L. Yang, W. Gu, Y. Chen, et al., Angew. Chem. Int. Ed. 57 (2018) 1096–1102. doi: 10.1002/anie.201712011
14. [14]
  Z. Ma, C. Xiao, C. Liu, et al., Org. Lett. 19 (2017) 4331–4334. doi: 10.1021/acs.orglett.7b02011
15. [15]
  K. Chen, N. Xue, G. Liu, et al., Chin. Chem. Lett. 34 (2023) 107884. doi: 10.1016/j.cclet.2022.107884
16. [16]
  J. Linshoeft, E.J. Baum, A. Hussain, et al., Angew. Chem. Int. Ed. 53 (2014) 12916–12920. doi: 10.1002/anie.201407377
17. [17]
  S. Urrego-Riveros, I.M. Ramirez y Medina, J. Hoffmann, et al., Chem. Eur. J. 24 (2018) 5680–5696. doi: 10.1002/chem.201703533
18. [18]
  R.S. Mulliken, J. Chem. Phys. 7 (1939) 339–352. doi: 10.1063/1.1750446
19. [19]
  I.V. Alabugin, K.M. Gilmore, P.W. Peterson, WIREs Comput. Mol. Sci. 1 (2011) 109–141. doi: 10.1002/wcms.6
20. [20]
  E.H. Braye, W. Hübel, I. Caplier, J. Am. Chem. Soc. 83 (1961) 4406–4413. doi: 10.1021/ja01482a026
21. [21]
  P.J. Fagan, W.A. Nugent, J.C. Calabrese, J. Am. Chem. Soc. 116 (1994) 1880–1889. doi: 10.1021/ja00084a031
22. [22]
  J. Dubac, A. Laporterie, G. Manuel, Chem. Rev. 90 (1990) 215–263. doi: 10.1021/cr00099a008
23. [23]
  X. Yan, C. Xi, Acc. Chem. Res. 48 (2015) 935–946. doi: 10.1021/ar500429f
24. [24]
  J. Krause, K.J. Haack, K.R. Pörschke, et al., J. Am. Chem. Soc. 118 (1996) 804–821. doi: 10.1021/ja952495b
25. [25]
  S. Yasuike, T. Iida, S. Okajima, et al., Tetrahedron 57 (2001) 10047–10053. doi: 10.1016/S0040-4020(01)01067-5
26. [26]
  D. Azarian, S.S. Dua, C. Eaborn, et al., J. Organometal. Chem. 117 (1976) C55–C57. doi: 10.1016/S0022-328X(00)91902-8
27. [27]
  H. Azizian, C. Eaborn, A. Pidcock, J. Organometal. Chem. 215 (1981) 49–58. doi: 10.1016/S0022-328X(00)84615-X
28. [28]
  A. Steffen, R.M. Ward, W.D. Jones, et al., Coord. Chem. Rev. 254 (2010) 1950–1976. doi: 10.1016/j.ccr.2010.03.002
29. [29]
  J. Dupont, C.S. Consorti, J. Spencer, Chem. Rev. 105 (2005) 2527–2572. doi: 10.1021/cr030681r
30. [30]
  D. Masselot, J.P.H. Charmant, T. Gallagher, J. Am. Chem. Soc. 128 (2006) 694–695. doi: 10.1021/ja056964d
31. [31]
  G. Shi, D. Chen, H. Jiang, et al., Org. Lett. 18 (2016) 2958–2961. doi: 10.1021/acs.orglett.6b01300
32. [32]
  S. Pan, H. Jiang, Y. Zhang, et al., Org. Lett. 18 (2016) 5192–5195. doi: 10.1021/acs.orglett.6b02071
33. [33]
  G. Gao, N. Liang, H. Geng, et al., J. Am. Chem. Soc. 139 (2017) 15914–15920. doi: 10.1021/jacs.7b09140
34. [34]
  K.M. Felter, R.K. Dubey, F.C. Grozema, J. Chem. Phys. 151 (2019) 094301. doi: 10.1063/1.5110306
35. [35]
  S. Yamaguchi, Y. Itami, K. Tamao, Organometallics 17 (1998) 4910–4916. doi: 10.1021/om980393z
36. [36]
  M. Hissler, P.W. Dyer, R. Réau, Coord. Chem. Rev. 244 (2003) 1–44. doi: 10.1016/S0010-8545(03)00098-5
37. [37]
  D. Tanaka, J. Ohshita, Y. Ooyama, et al., Organometallics 32 (2013) 4136–4141. doi: 10.1021/om400213q
38. [38]
  A.A. Rachford, S. Goeb, F.N. Castellano, J. Am. Chem. Soc. 130 (2008) 2766–2767. doi: 10.1021/ja800333y
39. [39]
  Y. Usui, Chem. Lett. 2 (1973) 743–744. doi: 10.1246/cl.1973.743
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