Citation: Jingyuan Yang, Xinyu Tian, Liuzhong Yuan, Yu Liu, Yue Wang, Chuandong Dou. Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching[J]. Chinese Chemical Letters, ;2024, 35(8): 109745. doi: 10.1016/j.cclet.2024.109745 shu

Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching

Jingyuan Yang ^a ,
Xinyu Tian ^a ,
Liuzhong Yuan ^a ,
Yu Liu ^{a, *,} ,
Yue Wang ^a ,
Chuandong Dou ^{a, b, *,}

a.
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
b.
Jiangsu Engineering Laboratory of Novel Functional Polymeric Materials, Soochow University, Suzhou 215123, China

yuliu@jlu.edu.cn

chuandong@jlu.edu.cn

Received Date: 28 December 2023
Revised Date: 28 February 2024
Accepted Date: 5 March 2024
Available Online: 9 March 2024

Figures(8)

Diradical polycyclic hydrocarbons (PHs) have unique open-shell structures and interesting physical properties. However, owing to high reactivity of unpaired electrons, such open-shell organic diradicaloids are usually less stable than closed-shell systems, limiting their practical applications. In this study, we report P=O-attaching of diradical PHs as a new strategy to enhance their stability while maintaining diradical properties. Three P=O-attached PHs containing the indeno[1,2-b]fluorene, fluoreno[3,2-b]fluorene and indeno[2,1-b]fluorene π-skeletons, respectively, were designed and synthesized. As theoretically and experimentally proved, two of them have the relatively large diradical characters and open-shell singlet diradical nature. In comparison to their all-carbon analogues, the attached electron-withdrawing P=O groups endow them with much lower LUMO/HOMO energy levels but preserved magnetic activities and physical properties, such as thermally accessible triplet species and multi-redox ability. Moreover, the P=O groups effectively decrease their oxidation activities and thereby lead to their remarkably excellent ambient stabilities. Thus, this P=O-attaching strategy will be applicable to other diradical PH systems and may promote the generation of stable organic diradicaloids for radical chemistry and materials.
- Polycyclic hydrocarbons,
- Open-shell structure,
- Diradical character,
- Stability,
- Oxidation activity
1. [1]
  J.J. Dressler, M.M. Haley, J. Phy. Org. Chem. 33 (2020) e4114. doi: 10.1002/poc.4114
2. [2]
  T. Kubo, Chem. Rec. 15 (2015) 218–232. doi: 10.1002/tcr.201402065
3. [3]
  T.Y. Gopalakrishna, W. Zeng, X. Lu, et al., Chem. Commun. 54 (2018) 2186–2199. doi: 10.1039/C7CC09949E
4. [4]
  Z. Cui, A. Abdurahman, X. Ai, et al., CCS Chem. 2 (2020) 1129–1145. doi: 10.31635/ccschem.020.202000210
5. [5]
  X. Hu, W. Wang, D. Wang, et al., J. Mater. Chem. C 6 (2018) 11232–11242. doi: 10.1039/C8TC04484H
6. [6]
  A. Konishi, Y. Hirao, K. Matsumoto, et al., J. Am. Chem. Soc. 135 (2013) 1430–1437. doi: 10.1021/ja309599m
7. [7]
  M. Chen, Y. Duan, X. Liu, et al., CCS Chem. 6 (2024) 353–364. doi: 10.31635/ccschem.023.202302848
8. [8]
  P. Hu, S. Lee, T.S. Herng, et al., J. Am. Chem. Soc. 138 (2016) 1065–1077. doi: 10.1021/jacs.5b12532
9. [9]
  G.E. Rudebusch, J.L. Zafra, K. Jorner, et al., Nat. Chem. 8 (2016) 753–759. doi: 10.1038/nchem.2518
10. [10]
  Y. Ni, T.Y. Gopalakrishna, H. Phan, et al., Angew. Chem. Int. Ed. 57 (2018) 9697–9701. doi: 10.1002/anie.201804276
11. [11]
  J. Liu, S. Mishra, C.A. Pignedoli, et al., J. Am. Chem. Soc. 141 (2019) 12011–12020. doi: 10.1021/jacs.9b04718
12. [12]
  Z.X. Chen, Y. Li, F. Huang, Chem 7 (2021) 288–332. doi: 10.1016/j.chempr.2020.09.024
13. [13]
  D.T. Chase, A.G. Fix, S.J. Kang, et al., J. Am. Chem. Soc. 134 (2012) 10349–10352. doi: 10.1021/ja303402p
14. [14]
  J.E. Barker, C.K. Frederickson, M.H. Jones, et al., Org. Lett. 19 (2017) 5312–5315. doi: 10.1021/acs.orglett.7b02605
15. [15]
  A. Shimizu, R. Kishi, M. Nakano, et al., Angew. Chem. Int. Ed. 52 (2013) 6076–6079. doi: 10.1002/anie.201302091
16. [16]
  K. Sahara, M. Abe, H. Zipse, et al., J. Am. Chem. Soc. 142 (2020) 5408–5418. doi: 10.1021/jacs.0c01003
17. [17]
  C.K. Frederickson, B.D. Rose, M.M. Haley, Acc. Chem. Res. 50 (2017) 977–987. doi: 10.1021/acs.accounts.7b00004
18. [18]
  H. Han, D. Zhang, Z. Zhu, et al., J. Am. Chem. Soc. 143 (2021) 17690–17700. doi: 10.1021/jacs.1c08262
19. [19]
  A. Konishi, Y. Hirao, M. Nakano, et al., J. Am. Chem. Soc. 132 (2010) 11021–11023. doi: 10.1021/ja1049737
20. [20]
  J. Ma, J. Liu, M. Baumgarten, et al., Angew. Chem. Int. Ed. 56 (2017) 3280–3284. doi: 10.1002/anie.201611689
21. [21]
  T. Shen, Y. Zou, X. Hou, et al., Angew. Chem. Int. Ed. 62 (2023) e202311928. doi: 10.1002/anie.202311928
22. [22]
  Y. Li, W.K. Heng, B.S. Lee, et al., J. Am. Chem. Soc. 134 (2012) 14913–14922. doi: 10.1021/ja304618v
23. [23]
  J. Guo, Z. Li, J. Zhang, et al., CCS Chem. 4 (2022) 95–103. doi: 10.31635/ccschem.021.202000658
24. [24]
  A. Shimizu, M. Uruichi, K. Yakushi, et al., Angew. Chem. Int. Ed. 48 (2009) 5482–5486. doi: 10.1002/anie.200901382
25. [25]
  W. Zeng, H. Phan, T.S. Herng, et al., Chem 2 (2017) 81–92. doi: 10.1016/j.chempr.2016.12.001
26. [26]
  R. Lu, S. Wu, L. Yang, et al., Angew. Chem. Int. Ed. 58 (2019) 7600–7605. doi: 10.1002/anie.201902028
27. [27]
  X. Shi, C. Chi, Top. Curr. Chem. 375 (2017) 68. doi: 10.1007/s41061-017-0154-3
28. [28]
  M. Hirai, N. Tanaka, M. Sakai, et al., Chem. Rev. 119 (2019) 8291–8331. doi: 10.1021/acs.chemrev.8b00637
29. [29]
  Z. Feng, S. Tang, Y. Su, et al., Chem. Soc. Rev. 51 (2022) 5930–5973. doi: 10.1039/D2CS00288D
30. [30]
  J.E. Barker, J.J. Dressler, A. Cárdenas Valdivia, et al., J. Am. Chem. Soc. 142 (2020) 1548–1555. doi: 10.1021/jacs.9b11898
31. [31]
  X. Zhang, J. Fang, C. Cai, et al., Chin. Chem. Lett. 32 (2021) 1280–1292. doi: 10.1016/j.cclet.2020.09.058
32. [32]
  L. Yuan, J. Guo, Y. Yang, et al., CCS Chem. 5 (2023) 876–884. doi: 10.31635/ccschem.022.202101738
33. [33]
  J. Guo, Z. Li, T. Zhang, et al., Chin. Chem. Lett. 35 (2024) 109337. doi: 10.1016/j.cclet.2023.109337
34. [34]
  L. Ma, S. Wang, Y. Li, et al., CCS Chem. 4 (2022) 3669–3676. doi: 10.31635/ccschem.022.202201954
35. [35]
  L. Mao, M. Zhou, X. Shi, et al., Chin. Chem. Lett. 32 (2021) 3331–3341. doi: 10.1016/j.cclet.2021.05.004
36. [36]
  Y. Liu, L. Yuan, J. Guo, et al., Angew. Chem. Int. Ed. 62 (2023) e202306911. doi: 10.1002/anie.202306911
37. [37]
  J.J. Dressler, M. Teraoka, G.L. Espejo, et al., Nat. Chem. 10 (2018) 1134–1140. doi: 10.1038/s41557-018-0133-5
38. [38]
  Z. Wang, Y. Dai, L. Ding, et al., Angew. Chem. Int. Ed. 60 (2021) 4594–4598. doi: 10.1002/anie.202012989
39. [39]
  J. Guo, Y. Yang, C. Dou, et al., J. Am. Chem. Soc. 143 (2021) 18272–18279. doi: 10.1021/jacs.1c08486
40. [40]
  J. Guo, Z. Li, X. Tian, et al., Angew. Chem. Int. Ed. 62 (2023) e202217470. doi: 10.1002/anie.202217470
41. [41]
  Z. Li, T. Sun, J. Guo, et al., Org. Chem. Front. 10 (2023) 4289–4297. doi: 10.1039/D3QO00900A
42. [42]
  L. Yuan, J. Yang, S. Qi, et al., Angew. Chem. Int. Ed. 62 (2023) e202314982. doi: 10.1002/anie.202314982
43. [43]
  J. Guo, X. Tian, Y. Wang, et al., Chem. Res. Chin. Univ. 39 (2023) 161–169. doi: 10.1007/s40242-023-2363-3
44. [44]
  T. Baumgartner, Acc. Chem. Res. 47 (2014) 1613–1622. doi: 10.1021/ar500084b
45. [45]
  D. Käch, A.C. Gasser, L. Wettstein, et al., Angew. Chem. Int. Ed. 62 (2023) e202304600. doi: 10.1002/anie.202304600
46. [46]
  M.P. Duffy, W. Delaunay, P.A. Bouit, et al., Chem. Soc. Rev. 45 (2016) 5296–5310. doi: 10.1039/C6CS00257A
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