Citation: Yu He, Hao Jiang, Shaoxuan Yuan, Jiayi Lu, Qiang Sun. On-surface photo-induced dechlorination[J]. Chinese Chemical Letters, ;2024, 35(9): 109807. doi: 10.1016/j.cclet.2024.109807 shu

On-surface photo-induced dechlorination

Materials Genome Institute, Shanghai University, Shanghai 200444, China

qiangsun@shu.edu.cn

Received Date: 18 January 2024
Revised Date: 14 March 2024
Accepted Date: 20 March 2024
Available Online: 22 March 2024

Figures(5)

On-surface Ullmann-type reaction, or the dehalogenated coupling, is arguably the most pivotal reaction in on-surface synthesis for the fabrications of carbon nanostructures. Hitherto, the vast majority of works rely on activating the C-Br bond of aryl bromide which has a moderate bond dissociation energy. The C-Cl bond of aryl chloride has a higher dissociation energy and requires much higher thermal energy to break the bond. In this study, we have explored the on-surface photo-induced dechlorination and achieved the activation of three distinct aryl chlorines on the Au(111) surface with mild temperatures. This work enriches our understanding of on-surface photo-induced reactions and highlights the potential of photochemistry in realizing unconventional reactions.
- On-surface synthesis,
- Scanning probe microscopy,
- On-surface photochemistry,
- Dechlorination reaction
1. [1]
  N.R. Champness, Nat. Nanotech. 2 (2007) 671–672. doi: 10.1038/nnano.2007.355
2. [2]
  Q. Shen, H.Y. Gao, H. Fuchs, Nano Today 13 (2017) 77–96. doi: 10.1016/j.nantod.2017.02.007
3. [3]
  S. Song, J. Su, M. Telychko, et al., Chem. Soc. Rev. 50 (2021) 3238–3262. doi: 10.1039/d0cs01060j
4. [4]
  S. Clair, D.G. de Oteyza, Chem. Rev. 119 (2019) 4717–4776. doi: 10.1021/acs.chemrev.8b00601
5. [5]
  L. Grill, S. Hecht, Nat. Chem. 12 (2020) 115–130. doi: 10.1038/s41557-019-0392-9
6. [6]
  J. Björk, F. Hanke, S. Stafström, J. Am. Chem. Soc. 135 (2013) 5768–5775. doi: 10.1021/ja400304b
7. [7]
  J. Björk, C. Sánchez-Sánchez, Q. Chen, et al., Angew. Chem. Int. Ed. 61 (2022) e202212354. doi: 10.1002/anie.202212354
8. [8]
  C. Ma, Z. Xiao, P.V. Bonnesen, et al., Chem. Sci. 12 (2021) 15637–15644. doi: 10.1039/d1sc04908a
9. [9]
  M. Lackinger, Chem. Commun. 53 (2017) 7872–7885. doi: 10.1039/C7CC03402D
10. [10]
  L. Lafferentz, F. Ample, H. Yu, et al., Science 323 (2009) 1193–1197. doi: 10.1126/science.1168255
11. [11]
  L. Grill, M. Dyer, L. Lafferentz, et al., Nat. Nanotechnol. 2 (2007) 687–691. doi: 10.1038/nnano.2007.346
12. [12]
  H. Jiang, J. Lu, F. Zheng, et al., Chem. Commun. 59 (2023) 8067–8070. doi: 10.1039/d3cc00167a
13. [13]
  J. Eichhorn, D. Nieckarz, O. Ochs, et al., ACS Nano 8 (2014) 7880–7889. doi: 10.1021/nn501567p
14. [14]
  M. Di Giovannantonio, M. El Garah, J. Lipton-Duffin, et al., ACS Nano 7 (2013) 8190–8198. doi: 10.1021/nn4035684
15. [15]
  J. Cai, P. Ruffieux, R. Jaafar, et al., Nature 466 (2010) 470–473. doi: 10.1038/nature09211
16. [16]
  C. Ma, J. Wang, H. Ma, et al., J. Am. Chem. Soc. 145 (2023) 10126–10135. doi: 10.1021/jacs.3c00563
17. [17]
  D.Y. Li, X. Qiu, S.W. Li, et al., J. Am. Chem. Soc. 143 (2021) 12955–12960. doi: 10.1021/jacs.1c05586
18. [18]
  R. Pawlak, X. Liu, S. Ninova, et al., J. Am. Chem. Soc. 142 (2020) 12568–12573. doi: 10.1021/jacs.0c03946
19. [19]
  B. Cirera, A. Sánchez-Grande, B. de la Torre, et al., Nat. Nanotechnol. 15 (2020) 437–443. doi: 10.1038/s41565-020-0668-7
20. [20]
  R.D. McCurdy, A. Delgado, J. Jiang, et al., J. Am. Chem. Soc. 145 (2023) 15162–15170. doi: 10.1021/jacs.3c01576
21. [21]
  Y. Zhang, J. Lu, Y. Li, et al., Angew. Chem. Int. Ed. 61 (2022) e202204736. doi: 10.1002/anie.202204736
22. [22]
  Q. Sun, H. Jiang, Y. Yan, R. Fasel, P. Ruffieux, Nano Res. 15 (2022) 8465–8469. doi: 10.1007/s12274-022-4410-7
23. [23]
  Q. Sun, Y. Yan, X. Yao, et al., J. Phys. Chem. Lett. 12 (2021) 8679–8684. doi: 10.1021/acs.jpclett.1c02541
24. [24]
  H. Zhang, J. Lu, Y. Zhang, et al., Chin. Chem. Lett. 34 (2023) 107450. doi: 10.1016/j.cclet.2022.04.048
25. [25]
  F. Xiang, S. Maisel, S. Beniwal, et al., Nat. Chem. 14 (2022) 871–876. doi: 10.1038/s41557-022-00968-3
26. [26]
  B. Yuan, C. Li, Y. Zhao, et al., J. Am. Chem. Soc. 142 (2020) 10034–10041. doi: 10.1021/jacs.0c01930
27. [27]
  X. Zhu, Y. Liu, W. Pu, et al., ACS Nano 16 (2022) 10600–10607. doi: 10.1021/acsnano.2c02163
28. [28]
  M. Di Giovannantonio, X. Yao, K. Eimre, et al., J. Am. Chem. Soc. 142 (2020) 12046–12050. doi: 10.1021/jacs.0c05268
29. [29]
  Q. Zhong, K. Niu, L. Chen, et al., J. Am. Chem. Soc. 144 (2022) 8214–8222. doi: 10.1021/jacs.2c01338
30. [30]
  Z. Zeng, D. Guo, T. Wang, et al., J. Am. Chem. Soc. 144 (2022) 723–732. doi: 10.1021/jacs.1c08284
31. [31]
  Q. Fan, L. Yan, M.W. Tripp, et al., Science 372 (2021) 852–856. doi: 10.1126/science.abg4509
32. [32]
  F. Palmino, C. Loppacher, F. Chérioux, ChemPhysChem 20 (2019) 2271–2280. doi: 10.1002/cphc.201900312
33. [33]
  K.J. Shi, D.W. Yuan, C.X. Wang, et al., Org. Lett. 18 (2016) 1282–1285. doi: 10.1021/acs.orglett.6b00172
34. [34]
  F. Schulz, P.H. Jacobse, F.F. Canova, et al., J. Phys. Chem. C 121 (2017) 2896–2904. doi: 10.1021/acs.jpcc.6b12428
35. [35]
  P.H. Jacobse, A. van den Hoogenband, M.E. Moret, R.J.M. Klein Gebbink, I. Swart, Angew. Chem. Int. Ed. 55 (2016) 13052–13055. doi: 10.1002/anie.201606440
36. [36]
  S.W. Hla, L. Bartels, G. Meyer, K.H. Rieder, Phys. Rev. Lett. 85 (2000) 2777. doi: 10.1103/PhysRevLett.85.2777
37. [37]
  Q. Zhong, A. Ihle, S. Ahles, et al., Nat. Chem. 13 (2021) 1133–1139. doi: 10.1038/s41557-021-00773-4
38. [38]
  Y. Wang, M. Zhong, J. Li, et al., Chin. Chem. Lett. 33 (2022) 1074–1076. doi: 10.1016/j.cclet.2021.05.060
39. [39]
  M. Zhong, Q. Wu, L. Ma, et al., Chin. Chem. Lett. 34 (2023) 107813. doi: 10.1016/j.cclet.2022.107813
40. [40]
  S. Clair, O. Ourdjini, M. Abel, L. Porte, Chem. Commun. 47 (2011) 8028–8030. doi: 10.1039/c1cc12065d
41. [41]
  C. Nacci, M. Schied, D. Civita, et al., J. Phys. Chem. C 125 (2021) 22554–22561. doi: 10.1021/acs.jpcc.1c06914
42. [42]
  J.I. Urgel, S. Mishra, H. Hayashi, et al., Nat. Commun. 10 (2019) 861. doi: 10.1038/s41467-019-08650-y
43. [43]
  H. Böckmann, S. Liu, J. Mielke, et al., Nano Lett. 16 (2016) 1034–1041. doi: 10.1021/acs.nanolett.5b04092
44. [44]
  E. Kazuma, J. Jung, H. Ueba, M. Trenary, Y. Kim, J. Am. Chem. Soc. 139 (2017) 3115–3121. doi: 10.1021/jacs.6b12680
45. [45]
  H.Y. Gao, D. Zhong, H. Mönig, et al., J. Phys. Chem. C 118 (2014) 6272–6277. doi: 10.1021/jp411889e
46. [46]
  A. Basagni, L. Ferrighi, M. Cattelan, et al., Chem. Commun. 51 (2015) 12593–12596. doi: 10.1039/C5CC04317D
47. [47]
  H. Jiang, Y. He, J. Lu, et al., ACS Nano 18 (2023) 1118–1125. doi: 10.1158/2767-9764.crc-23-0054
48. [48]
  E. Kazuma, J. Jung, H. Ueba, et al., Prog. Surf. Sci. 93 (2018) 163–176. doi: 10.1016/j.progsurf.2018.08.003
49. [49]
  J.C. Moreno-López, D.J. Mowbray, A. Pérez Paz, et al., Chem. Mater. 31 (2019) 3009–3017. doi: 10.1021/acs.chemmater.9b00668
50. [50]
  R.C. de Campos Ferreira, A. Pérez Paz, D.J. Mowbray, et al., Phys. Chem. C 124 (2020) 14220–14228. doi: 10.1021/acs.jpcc.0c02953
51. [51]
  R. Zuzak, P. Brandimarte, P. Olszowski, et al., J. Phys. Chem. Lett. 11 (2020) 10290–10297. doi: 10.1021/acs.jpclett.0c03134
52. [52]
  G. Galeotti, M.D. Giovannantonio, J. Lipton-Duffin, et al., Faraday Discuss. 204 (2017) 453–469. doi: 10.1039/C7FD00099E
53. [53]
  B.Z. Wu, H.Y. Chen, S.J. Wang, et al., Chemosphere 88 (2012) 757–768. doi: 10.1016/j.chemosphere.2012.03.056
54. [54]
  K.J. Shi, X. Zhang, C.H. Shu, et al., Chem. Commun. 52 (2016) 8726–8729. doi: 10.1039/C6CC03137D
55. [55]
  X. Zhou, F. Bebensee, Q. Shen, et al., Mater. Chem. Front. 1 (2017) 119–127. doi: 10.1039/C6QM00142D
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