Citation: Qiu Liang, Guangyuan Feng, Hongzhen Ni, Yaru Song, Xinyu Zhang, Shengbin Lei, Wenping Hu. Room temperature spontaneous surface condensation of boronic acids observed by scanning tunneling microscopy[J]. Chinese Chemical Letters, ;2023, 34(8): 108006. doi: 10.1016/j.cclet.2022.108006 shu

Room temperature spontaneous surface condensation of boronic acids observed by scanning tunneling microscopy

Qiu Liang ^{a, b} ,
Guangyuan Feng ^{a, *,} ,
Hongzhen Ni ^a ,
Yaru Song ^a ,
Xinyu Zhang ^a ,
Shengbin Lei ^{a, *,} ,
Wenping Hu ^a

a.
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Science & Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, China
b.
School of Foreign Languages, Henan University, Kaifeng 475000, China

fengguangyuan@tju.edu.cn

shengbin.lei@tju.edu.cn

Received Date: 5 September 2022
Revised Date: 23 October 2022
Accepted Date: 13 November 2022
Available Online: 16 November 2022

Figures(5)

Herein, we discovered that the surface-confined condensation of boronic acid can happen spontaneously at room temperature, by comparing the kinetics of condensation of boronic acids with and without the negative sample bias, we found that the negative sample bias indeed accelerates the self-condensation reaction of boronic acid. Combining with in-situ STM images and ultraviolet photoemission spectrum (UPS) analysis, a reversible adsorption mechanism model was proposed and reasonably explains the reversible electric-field-induced phase transformation.
- Boronic acids,
- Electric-field-induced condensation,
- Spontaneous condensation,
- Surface-confined synthesis,
- Scanning tunneling microscopy
1. [1]
  M. Lackinger, Nature 572 (2019) 448–449. doi: 10.1038/d41586-019-02452-4
2. [2]
  L. Grossmann, B.T. King, S. Reichlmaier, et al., Nat. Chem. 13 (2021) 730–736. doi: 10.1038/s41557-021-00709-y
3. [3]
  M.M. Abadía, C.T. Stoppiello, K. Strutynski, et al., J. Am. Chem. Soc. 141 (2019) 14403–14410. doi: 10.1021/jacs.9b07383
4. [4]
  S.W. Park, Z.Q. Liao, B. Ibarlucea, et al., Angew. Chem. Int. Ed. 59 (2020) 8218–8224. doi: 10.1002/anie.201916595
5. [5]
  C. Moreno, M.V. Varela, B. Kretz, et al., Science 360 (2018) 199–203. doi: 10.1126/science.aar2009
6. [6]
  G. Galeotti , F.D. Marchi , E. Hamzehpoor , et al., Nat. Mater. 19 (2020) 874–880. doi: 10.1038/s41563-020-0682-z
7. [7]
  J.C. Lai, J.F. Mei, X.Y. Jia, et al., Adv. Mater. 28 (2016) 8277–8282. doi: 10.1002/adma.201602332
8. [8]
  Q.W. Zhu, M. Saeed, R.D. Song, et al., Chin. Chem. Lett. 31 (2020) 1051–1059. doi: 10.1016/j.cclet.2019.12.002
9. [9]
  J. Cao, C.H. Lu, J. Zhuang, et al., Angew. Chem. Int. Ed. 56 (2017) 8795–8800. doi: 10.1002/anie.201704217
10. [10]
  O.R. Cromwell, J. Chung, Z. Guan, J. Am. Chem. Soc. 137 (2015) 6492–6495. doi: 10.1021/jacs.5b03551
11. [11]
  J.J. Cash, T. Kubo, A.P. Bapat, B.S. Sumerlin, Macromolecules 48 (2015), 2098–2106. doi: 10.1021/acs.macromol.5b00210
12. [12]
  M. Sassi, V. Oison, J.M. Debierre, S. Humbel, ChemPhysChem 10 (2009) 2480–2485. doi: 10.1002/cphc.200900168
13. [13]
  S. Clair, M. Abel, L. Porte, Chem. Commun. 50 (2014) 9627–9635. doi: 10.1039/C4CC02678K
14. [14]
  A.P. Cote, A.I. Benin, N.W. Ockwig, et al., Science 310 (2005) 1166–1170. doi: 10.1126/science.1120411
15. [15]
  N.A.A. Zwaneveld, R. Pawlak, M. Abel, et al., J. Am. Chem. Soc. 130 (2008) 6678–6679. doi: 10.1021/ja800906f
16. [16]
  J.F. Dienstmaier, D.D. Medina, M. Dogru, et al., ACS Nano 6 (2012) 7234–7242. doi: 10.1021/nn302363d
17. [17]
  C.Z. Guan, D. Wang, L.J. Wan, Chem. Commun. 48 (2012) 2943–2945. doi: 10.1039/c2cc16892h
18. [18]
  J.F. Dienstmaier, A.M. Gigler, A.J. Goetz, et al., ACS Nano 5 (2011) 9737–9745. doi: 10.1021/nn2032616
19. [19]
  J. Plas, O. Ivasenko, N. Martsinovich, M. Lackinger, S.D. Feyter, Chem. Commun. 52 (2016) 68–71. doi: 10.1039/C5CC07557B
20. [20]
  Z.F. Cai, G.L. Zhan, L. Daukiya, et al., J. Am. Chem. Soc. 141 (2019) 11404–11408. doi: 10.1021/jacs.9b05265
21. [21]
  N. Bilbao, C. Martín, G.L. Zhan, et al., ACS Nano 14 (2020) 2354–2365. doi: 10.1021/acsnano.9b09520
22. [22]
  J. Plas, D. Waghray, J. Adisoejoso, et al., Chem. Commun. 51 (2015) 16338–16341. doi: 10.1039/C5CC06970J
23. [23]
  A. Ciesielski, M. El Garah, S. Haar, et al., Nat. Chem. 6 (2014) 1017–1023. doi: 10.1038/nchem.2057
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2. [2]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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