Citation: Shuanggen Wu, Wenbo Wang, Changyong Cai, Fenfang Li, Shengyi Dong. Low-molecular-weight supramolecular adhesive with resistance to low temperatures[J]. Chinese Chemical Letters, ;2023, 34(5): 107830. doi: 10.1016/j.cclet.2022.107830 shu

Low-molecular-weight supramolecular adhesive with resistance to low temperatures

a.
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
b.
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China

dongsy@hnu.edu.cn

Received Date: 20 June 2022
Revised Date: 7 September 2022
Accepted Date: 14 September 2022
Available Online: 17 September 2022

Figures(6)

The design of adhesive materials with strong adhesion capacity at low temperatures is a great challenge. Herein, we report a low-molecular-weight supramolecular adhesive that exhibits good adhesion performance to various surfaces at low temperatures (from −18 ℃ to −80 ℃). Moreover, this supramolecular adhesive has good adhesion ability in the presence of water.
- Supramolecular adhesive,
- Low temperature resistance,
- Underwater adhesion,
- Low-molecular-weight monomer,
- Supramolecular adhesion
1. [1]
  J. Courtois, I. Baroudi, N. Nouvel, et al., Adv. Funct. Mater. 20 (2010) 1803–1811. doi: 10.1002/adfm.200901903
2. [2]
  S.J. Cheng, M.Q. Zhang, N. Dixit, R.B. Moore, T.E. Long, Macromolecules 45 (2012) 805–812. doi: 10.1021/ma202122r
3. [3]
  C. Heinzmann, C. Weder, L.M. de Espinosa, Chem. Soc. Rev. 45 (2016) 342–358. doi: 10.1039/C5CS00477B
4. [4]
  C.Y. Shi, Q. Zhang, H. Tian, D.H. Qu, SmartMat 1 (2020) e1012.
5. [5]
  Y. Zhao, S.L. Song, X.Z. Ren, et al., Chem. Rev. 122 (2022) 5604–5640. doi: 10.1021/acs.chemrev.1c00815
6. [6]
  Q. Zhang, C.Y. Shi, D.H. Qu, et al., Sci. Adv. 4 (2018) eaat8192. doi: 10.1126/sciadv.aat8192
7. [7]
  S.H. Mostafavi, F. Tong, T.W. Dugger, D. Kisailus, C.J. Bardeen, Macromolecules 51 (2018) 2388–2394. doi: 10.1021/acs.macromol.8b00036
8. [8]
  X.F. Ji, M. Ahmed, L.L. Long, et al., Chem. Soc. Rev. 48 (2019) 2682–2697. doi: 10.1039/C8CS00955D
9. [9]
  W. Zhang, Y. Luo, J. Zhao, et al., Chin. Chem. Lett. 33 (2022) 2455–2458. doi: 10.1016/j.cclet.2021.11.053
10. [10]
  B. Zhao, L. Jiang, Q. Jiang, Chin. Chem. Lett. 33 (2022) 11–21. doi: 10.1016/j.cclet.2021.06.031
11. [11]
  C.A. Anderson, A.R. Jones, E.M. Briggs, et al., J. Am. Chem. Soc. 135 (2013) 7288–7295. doi: 10.1021/ja4005283
12. [12]
  D.L. Gan, W.S. Xing, L.L. Jiang, et al., Nat. Commun. 10 (2019) 1487. doi: 10.1038/s41467-019-09351-2
13. [13]
  J.Y. Chen, D.W. Guo, S.H. Liang, Z.Z. Liu, Polym. Chem. 11 (2020) 6670–6680. doi: 10.1039/D0PY00926A
14. [14]
  M.G. Mazzotta, A.A. Putnam, M.A. North, J.J. Wilker, J. Am. Chem. Soc. 142 (2020) 4762–4768. doi: 10.1021/jacs.9b13356
15. [15]
  S.G. Wu, C.Y. Cai, F.F. Li, Z.J. Tan, S.Y. Dong, CCS Chem. 2 (2020) 1690–1700.
16. [16]
  X. Li, Z.L. Wang, W. Li, J.Q. Sun, ACS Mater. Lett. 3 (2021) 875–882. doi: 10.1021/acsmaterialslett.1c00167
17. [17]
  M.W.M. Tan, G. Thangavel, P.S. Lee, Adv. Funct. Mater. 31 (2021) 2103097. doi: 10.1002/adfm.202103097
18. [18]
  C.Y. Cai, S.G. Wu, Z.J. Tan, F.F. Li, S.Y. Dong, ACS Appl. Mater. Interfaces 13 (2021) 53083–53090. doi: 10.1021/acsami.1c15959
19. [19]
  H. Xu, X.Y. Jiang, X.S. Han, H.Z. Cai, F. Gao, J. Mater. Chem. A 9 (2021) 25104–25113. doi: 10.1039/D1TA07273K
20. [20]
  S. Xia, Y.K. Chen, J.F. Tian, et al., Adv. Funct. Mater. 31 (2021) 2101143. doi: 10.1002/adfm.202101143
21. [21]
  D.W.R. Balkenende, C.A. Monnier, G.L. Fiore, C. Weder, Nat. Commun. 7 (2016) 10995. doi: 10.1038/ncomms10995
22. [22]
  A. Lavrenova, D.W.R. Balkenende, Y. Sagara, et al., J. Am. Chem. Soc. 139 (2017) 4302–4305. doi: 10.1021/jacs.7b00342
23. [23]
  J. Courtois, I. Baroudi, N. Nouvel, et al., Adv. Funct. Mater. 20 (2010) 1803–1811. doi: 10.1002/adfm.200901903
24. [24]
  C. Heinzmann, U. Salz, N. Moszner, G.L. Fiore, C. Weder, ACS Appl. Mater. Interfaces 7 (2015) 13395–13404. doi: 10.1021/acsami.5b01939
25. [25]
  X. Li, N. Mignard, M. Taha, et al., Macromolecules 52 (2019) 6585–6599. doi: 10.1021/acs.macromol.9b00585
26. [26]
  H.B. Gao, X.D. Ma, J.P. Lin, et al., Macromolecules 52 (2019) 7731–7739. doi: 10.1021/acs.macromol.9b01358
27. [27]
  R.D. Adams, V. Mallick, J. Adhes. 43 (1993) 17–33. doi: 10.1080/00218469308026585
28. [28]
  S.G. Kang, M.G. Kim, C.G. Kim, Compos. Struct. 78 (2007) 440–446. doi: 10.1016/j.compstruct.2005.11.005
29. [29]
  J.J.M. Machado, E.A.S. Marques, L.F.M. da Silva, Compos. Struct. 194 (2018) 68–79. doi: 10.1016/j.compstruct.2018.03.093
30. [30]
  J.J. Xu, R.J. Jing, X.Y. Ren, G.H. Gao, J. Mater. Chem. A 8 (2020) 9373–9381. doi: 10.1039/D0TA02370A
31. [31]
  X. Li, J.L. Lai, Y. Deng, et al., J. Am. Chem. Soc. 142 (2020) 21522–21529. doi: 10.1021/jacs.0c10786
32. [32]
  X. Su, H. Wang, Z.L. Tian, et al., ACS Appl. Mater. Interfaces 12 (2020) 29757–29766.
33. [33]
  L. Wu, L.W. Li, M.J. Qu, H. Wang, Y.Z. Bin, ACS Appl. Polym. Mater. 2 (2020) 3094–3106. doi: 10.1021/acsapm.0c00264
34. [34]
  Y. Yao, Z.Y. Xu, B. Liu, et al., Adv. Funct. Mat. 31 (2021) 2006944. doi: 10.1002/adfm.202006944
35. [35]
  Y.J. Chen, Y.N. Zhang, A. Mensaha, et al., Carbohydr. Polym. 255 (2021) 117508. doi: 10.1016/j.carbpol.2020.117508
36. [36]
  J. Wen, J. Tang, H.M. Ning, et al., Adv. Funct. Mater. 31 (2021) 2011176. doi: 10.1002/adfm.202011176
37. [37]
  S.G. Wu, Q. Zhang, Y. Deng, et al., J. Am. Chem. Soc. 142 (2020) 448–455. doi: 10.1021/jacs.9b11290
38. [38]
  J. Watte, W. van Gompel, P. Lemmens, et al., ACS Appl. Mater. Interfaces 8 (2016) 29759–29769. doi: 10.1021/acsami.6b08931
39. [39]
  S.Y. Dong, J. Leng, Y.X. Feng, et al., Sci. Adv. 3 (2017) eaao0900. doi: 10.1126/sciadv.aao0900
40. [40]
  Q. Zhang, T. Li, A.B. Duan, et al., J. Am. Chem. Soc. 141 (2019) 8058–8063. doi: 10.1021/jacs.9b02677
41. [41]
  X. Li, Y. Deng, J.L. Lai, G. Zhao, S.Y. Dong, J. Am. Chem. Soc. 142 (2020) 5371–5379. doi: 10.1021/jacs.0c00520
42. [42]
  Q.F. Rong, W.W. Lei, L. Chen, et al., Angew. Chem. Int. Ed. 56 (2017) 14159–14163. doi: 10.1002/anie.201708614
43. [43]
  S.W. Hao, L. Meng, Q.J. Fu, F. Xu, J. Yang, Chem. Eng. J. 431 (2022) 133782. doi: 10.1016/j.cej.2021.133782
44. [44]
  Y. Deng, X. Li, C. Han, S.Y. Dong, Chin. Chem. Lett. 31 (2020) 3221–3224. doi: 10.1016/j.cclet.2020.03.074
45. [45]
  M.M. Zhang, X.Z. Yan, F.H. Huang, Z.B. Niu, H.W. Gibson, Acc. Chem. Res. 47 (2014) 1995–2005. doi: 10.1021/ar500046r
46. [46]
  Z. Wu, C.D. Ji, X.J. Zhao, et al., J. Am. Chem. Soc. 141 (2019) 7385–7390. doi: 10.1021/jacs.9b01056
47. [47]
  D.K. Hohl, C. Weder, Adv. Opt. Mater. 7 (2019) 1900230. doi: 10.1002/adom.201900230
48. [48]
  T. Xiao, L. Zhou, X.Q. Sun, et al., Chin. Chem. Lett. 31 (2020) 1–9. doi: 10.1016/j.cclet.2019.05.011
49. [49]
  Q. Xu, Z. Cui, J. Yao, et al., Chin. Chem. Lett. 32 (2021) 4024–4028. doi: 10.1016/j.cclet.2021.05.058
50. [50]
  X. Zhao, Y. Liu, Z.Y. Zhang, et al., Angew. Chem. Int. Ed. 60 (2021) 17904–17909. doi: 10.1002/anie.202104875
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