Citation: Yuchuan Xiao, Fangjian Cai, Xuan Peng, Xiyuan Kang, Peng Lei, Xin Li, Haijun Xu, Xunwen Xiao, Bin Tu, Qingdao Zeng. Aza-BODIPY molecular assembly at the liquid-solid interface driven by Br…F—BF interactions[J]. Chinese Chemical Letters, ;2021, 32(11): 3566-3569. doi: 10.1016/j.cclet.2021.02.066 shu

Aza-BODIPY molecular assembly at the liquid-solid interface driven by Br…F—BF interactions

Yuchuan Xiao ^{a, c, d, 1} ,
Fangjian Cai ^{b, 1} ,
Xuan Peng ^{a, d, 1} ,
Xiyuan Kang ^b ,
Peng Lei ^{a, d} ,
Xin Li ^e ,
Haijun Xu ^{b, f, **,} ,
Xunwen Xiao ^{c, ***,} ,
Bin Tu ^{a, *,} ,
Qingdao Zeng ^{a, d, *,}

a.
CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology (NCNST), Beijing 100190, China
b.
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
c.
School of Materials and Chemical Engineering, Ningbo University of Technology, Ningbo 315211, China
d.
Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
e.
CAS Center for Excellence in Nanoscience, Beijing Key Laboratory of Micro-Nano Energy and Sensor, Beijing Institute of Nanoenergy and Nanosystems, Chinese Academy of Sciences, Beijing 100083, China
f.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453002, China

^**

^***

xuhaijun@njfu.edu.cn

xunwenxiao@nbut.edu.cn

tub@nanoctr.cn

zengqd@nanoctr.cn

Received Date: 11 January 2021
Revised Date: 19 February 2021
Accepted Date: 26 February 2021
Available Online: 1 March 2021

Figures(3)

In this work, two aza-BODIPY derivatives, 3,5-diphenyl-1,7-di(p-dodecyloxyphenyl)-aza-BODIPY (CJF) and 3,5-di(p-bromophenyl-1,7-di(p-dodecyloxyphenyl)-aza-BODIPY (2Br-CJF) acted as model molecules to form the self-assembly monolayers on the solid-liquid interface. With the utilizing of scanning tunnelling microscope (STM), we demonstrated that intermolecular Br…F—BF interactions existed in 2Br-CJF self-assembly structure and played an important role in strengthening the stability of 2Br-CJF self-assembly structure. This result is supported by density functional theory (DFT) calculation.
- Aza-BODIPY,
- STM,
- Br…F interaction,
- Self-assembly,
- Surface assembly
1. [1]
  K. Reichenbacher, H.I. Suss, J. Hulliger, Chem. Soc. Rev. 34 (2005) 22-30. doi: 10.1039/B406892K
2. [2]
  T.T. Bui, S. Dahaoui, C. Lecomte, G.R. Desiraju, E. Espinosa, Angew. Chem. Int. Ed. 48 (2009) 3838-3841. doi: 10.1002/anie.200805739
3. [3]
  S.K. Nayak, M.K. Reddy, T.N.G. Row, D. Chopra, Cryst. Growth Des. 11 (2011) 1578-1596. doi: 10.1021/cg101544z
4. [4]
  G.R. Desiraju, R. Parthasarathy, J. Am. Chem. Soc. 111 (1989) 8725-8726. doi: 10.1021/ja00205a027
5. [5]
  V.R. Pedireddi, D.S. Reddy, B.S. Goud, et al., J. Chem. Soc. Perkin Trans. 2 (1994) 2353-2360. doi: 10.1039/P29940002353
6. [6]
  E. Albright, J. Cann, A. Decken, S. Eisler, CrystEngComm 19 (2017) 1024-1027. doi: 10.1039/C6CE02339H
7. [7]
  J.S. Ovens, D.B. Leznoff, CrystEngComm 20 (2018) 1769-1773. doi: 10.1039/C7CE02167D
8. [8]
  S.A. Adonin, M.A. Bondarenko, A.S. Novikov, et al., CrystEngComm 21 (2019) 6666-6670. doi: 10.1039/C9CE01106D
9. [9]
  F. Silly, J. Phys. Chem. C 117 (2013) 20244-20249. doi: 10.1021/jp4057626
10. [10]
  Z. Guo, P. Yu, K. Sun, et al., Phys. Chem. Chem. Phys. 19 (2017) 31540-31544. doi: 10.1039/C7CP06027K
11. [11]
  B. Zha, J. Li, J. Wu, X. Miao, M. Zhang, New J. Chem. 43 (2019) 17182-17187. doi: 10.1039/C9NJ04726C
12. [12]
  J. Hou, B. Tu, Q. Zeng, C. Zhan, J. Yao, Chin. Chem. Lett. 31 (2020) 353-356. doi: 10.1016/j.cclet.2019.07.029
13. [13]
  X. Gong, J. Zhang, S. Jiang, Chem. Comm. 56 (2020) 3054-3057. doi: 10.1039/C9CC08768K
14. [14]
  F. Guan, Z. Song, F. Xin, et al., J. Bioresour. Bioprod. 5 (2020) 37-43. doi: 10.1016/j.jobab.2020.03.004
15. [15]
  D.W. Wei, H. Wei, A.C. Gauthier, et al., J. Bioresour. Bioprod. 5 (2020) 1-15. doi: 10.1016/j.jobab.2020.03.001
16. [16]
  A. Mukherjee, A. Sanz-Matias, G. Velpula, et al., Chem. Sci. 10 (2019) 3881-3891. doi: 10.1039/C8SC04499F
17. [17]
  B. Zha, M. Dong, X. Miao, et al., Nanoscale 9 (2017) 237-250. doi: 10.1039/C6NR07693A
18. [18]
  B. Zha, X. Miao, P. Liu, Y. Wu, W. Deng, Chem. Commun. 50 (2014) 9003-9006. doi: 10.1039/C4CC03687E
19. [19]
  Q.N. Zheng, X.H. Liu, T. Chen, et al., J. Am. Chem. Soc. 137 (2015) 6128-6131. doi: 10.1021/jacs.5b02206
20. [20]
  R. Gutzler, O. Ivasenko, C. Fu, et al., Chem. Commun. 47 (2011) 9453-9455. doi: 10.1039/c1cc13114a
21. [21]
  M. Dong, K. Miao, J. Wu, et al., J. Phys. Chem. C 123 (2019) 4349-4359. doi: 10.1021/acs.jpcc.8b12176
22. [22]
  A. Loudet, K. Burgess, Chem. Rev. 107 (2007) 4891-4932. doi: 10.1021/cr078381n
23. [23]
  N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 41 (2012) 1130-1172. doi: 10.1039/C1CS15132K
24. [24]
  T. Bura, N. Leclerc, S. Fall, et al., J. Am. Chem. Soc. 134 (2012) 17404-17407. doi: 10.1021/ja3072513
25. [25]
  W. Liu, A. Tang, J. Chen, et al., ACS Appl. Mater. Interfaces 6 (2014) 22496-22505. doi: 10.1021/am506585u
26. [26]
  J. Xu, W. Liu, Y. Geng, et al., Nanoscale 9 (2017) 2579-2584. doi: 10.1039/C6NR08234C
27. [27]
  J. Xu, Y. Li, L. Wang, et al., Chin. Chem. Lett. 30 (2019) 767-770. doi: 10.1016/j.cclet.2018.09.019
28. [28]
  J. Li, X. Zu, Y. Qian, et al., Chin. Chem. Lett. 31 (2020) 10-18. doi: 10.1016/j.cclet.2019.04.032
29. [29]
  J. Li, Y. Qian, W. Duan, Q. Zeng, Chin. Chem. Lett. 30 (2019) 292-298. doi: 10.1016/j.cclet.2018.05.037
30. [30]
  Q. Xue, Y. Zhang, R. Li, et al., Chin. Chem. Lett. 30 (2019) 2355-2358. doi: 10.1016/j.cclet.2019.09.027
31. [31]
  J. Hou, H. Dai, Z. Zhang, et al., Langmuir 33 (2017) 400-406. doi: 10.1021/acs.langmuir.6b03567
32. [32]
  X. Zhu, Y. Geng, H. Xiao, et al., Langmuir 34 (2018) 5169-5173. doi: 10.1021/acs.langmuir.7b04293
33. [33]
  J.P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 77 (1996) 3865-3868. doi: 10.1103/PhysRevLett.77.3865
34. [34]
  J.M. MacLeod, J.A. Lipton-Duffin, D. Cui, S. De Feyter, F. Rosei, Langmuir 31 (2015) 7016-7024. doi: 10.1021/la5048886
35. [35]
  H. Sun, A. Horatscheck, V. Martos, et al., Angew. Chem. Int. Ed. 56 (2017) 6454-6458. doi: 10.1002/anie.201700520
36. [36]
  H.G. Wallnoefer, T. Fox, K.R. Liedl, C.S. Tautermann, Phys. Chem. Chem. Phys. 12 (2010) 14941-14949. doi: 10.1039/c0cp00607f
37. [37]
  I.S. Youn, D.Y. Kim, J.W. Cho, et al., J. Phys. Chem. A 120 (2016) 9305-9314. doi: 10.1021/acs.jpca.6b09395
38. [38]
  L.N. Anderson, F.W. Aquino, A.E. Raeber, X. Chen, B.M. Wong, J. Chem. Theory Comput. 14 (2018) 180-190. doi: 10.1021/acs.jctc.7b01078
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