Citation: Guicong Hu, Wen Chang, Sai An, Bo Qi, Yu-Fei Song. Self-assembly of reverse micelle nanoreactors by zwitterionic polyoxometalate-based surfactants for high selective production of β-hydroxyl peroxides[J]. Chinese Chemical Letters, ;2022, 33(8): 3968-3972. doi: 10.1016/j.cclet.2021.11.006 shu

Self-assembly of reverse micelle nanoreactors by zwitterionic polyoxometalate-based surfactants for high selective production of β-hydroxyl peroxides

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China

bqi@mail.buct.edu.cn

songyf@mail.buct.edu.cn

Received Date: 6 October 2021
Revised Date: 27 October 2021
Accepted Date: 1 November 2021
Available Online: 7 November 2021

Figures(3)

Surfactants with polyoxometalates (POMs) as polar head groups have shown fascinating self-assembly behaviors and various functional applications. However, self-assembly them into reverse micelles is still challenging owing to the large molecular size and intermolecular strong electrostatic repulsions of POM heads. In this work, a zwitterionic POM-based surfactant was synthesized by covalently grafting two cationic long alkyl tails onto the lacunary site of [PW₁₁O₃₉]⁷⁻. With decreased electrostatic repulsions and increased hydrophobic effect, the POM-based reverse micelles with an average diameter of 5 nm were obtained. Interestingly, when these reverse micelles were applied for catalyzing the oxidation of styrene, an unprecedented β-hydroxyl peroxide compound of 2-hydroxyl-2-phenylethan-1-tert-butylperoxide was produced in high selectivity of 95.2%. In comparison, the cetyltrimethylammonium electrostatically encapsulated POMs mainly generated the epoxides or 1, 2-diols. A free radical mechanism was proposed for the oxidation reaction catalyzed by the zwitterionic POM surfactants.
- Polyoxometalate,
- Self-assembly,
- Peroxide,
- Catalysis,
- Zwitterionic surfactant
1. [1]
  F. Zaera, Chem. Soc. Rev. 42 (2013) 2746-2762. doi: 10.1039/C2CS35261C
2. [2]
  E.P. Melo, M.R. Aires-Barros, J.M.S. Cabral, Biotechnol. Annu. Rev. 7 (2001) 87-129.
3. [3]
  A. Küchler, M. Yoshimoto, S. Luginbühl, et al., Nat. Nanotech. 11 (2016) 409-420. doi: 10.1038/nnano.2016.54
4. [4]
  F. Moyano, R.D. Falcone, J.C. Mejuto, et al., Chem. Eur. J. 16 (2010) 8887-8893. doi: 10.1002/chem.201000437
5. [5]
  M. Moniruzzaman, N. Kamiya, M. Goto, et al., Langmuir 25 (2009) 977-982. doi: 10.1021/la803118q
6. [6]
  Y. Qian, W. Wen, P.A. Adcock, et al., J. Phys. Chem. C 112 (2008) 1146-1157. doi: 10.1021/jp074929i
7. [7]
  S. Polarz, S. Landsmann, A. Klaiber, Angew. Chem. Int. Ed. 53 (2014) 946-954. doi: 10.1002/anie.201303159
8. [8]
  P. Yin, J. Wang, Z. Xiao, et al., Chem. Eur. J. 18 (2012) 9174-9178. doi: 10.1002/chem.201201551
9. [9]
  H.K. Liu, L.J. Ren, H. Wu, et al., J. Am. Chem. Soc. 141 (2019) 831-839. doi: 10.1021/jacs.8b08016
10. [10]
  J. Xu, X. Li, J. Li, et al., Angew. Chem. Int. Ed. 56 (2017) 8731-8735. doi: 10.1002/anie.201703774
11. [11]
  S. Landsmann, C. Lizandara-Pueyo, S. Polarz, J. Am. Chem. Soc. 132 (2010) 5315-5321. doi: 10.1021/ja1011178
12. [12]
  J. Zhang, Y.F. Song, L. Cronin, et al., Chem. Eur. J. 16 (2010) 11320-11324. doi: 10.1002/chem.201000794
13. [13]
  C.G. Lin, W. Chen, S. Omwoma, et al., J. Mater. Chem. C 3 (2015) 15-18. doi: 10.1039/C4TC02142H
14. [14]
  G. Izzet, B. Abécassis, D. Brouri, et al., J. Am. Chem. Soc. 138 (2016) 5093-5099. doi: 10.1021/jacs.6b00972
15. [15]
  A. Proust, B. Matt, R. Villanneau, et al., Chem. Soc. Rev. 41 (2012) 7605-7622. doi: 10.1039/c2cs35119f
16. [16]
  D. Louvel, T.D.D. Miguel, N.D. Vu, et al., Eur. J. Org. Chem. (2021) 2990-3014.
17. [17]
  S.S. Wang, G.Y. Yang, Chem. Rev. 115 (2015) 4893-4962. doi: 10.1021/cr500390v
18. [18]
  G. Yang, Y. Liu, K. Li, et al., Chin. Chem. Lett. 31 (2020) 3233-3236. doi: 10.1016/j.cclet.2020.07.018
19. [19]
  W. Chang, B. Qi, Y.F. Song, ACS Appl. Mater. Interfaces 12 (2020) 36389-36397. doi: 10.1021/acsami.0c10207
20. [20]
  B. Qi, T. Zhang, M. Li, et al., Catal. Sci. Technol. 7 (2017) 5872-5881. doi: 10.1039/C7CY01892D
21. [21]
  Y. Chen, Y. Ma, L. Li, et al., Org. Lett. 21 (2019) 1480-1483. doi: 10.1021/acs.orglett.9b00266
22. [22]
  R.R. Ozer, J.L. Ferry, J. Phys. Chem. B 104 (2000) 9444-9448. doi: 10.1021/jp000783a
23. [23]
  G. Yang, X. Zhang, Y. Liu, et al., Inorg. Chem. Front. 8 (2021) 4650-4656. doi: 10.1039/D1QI00485A
24. [24]
  G. Yang, K. Li, X. Lin, et al., Chin. J. Chem. 39 (2021) 3017-3022. doi: 10.1002/cjoc.202100397
25. [25]
  G. Yang, X. Xie, M. Cheng, et al., Chin. Chem. Lett. 33 (2022) 1483-1487. doi: 10.1016/j.cclet.2021.08.037
26. [26]
  M. Zhao, X. Zhu, Y. Li, et al., Tungsten 4 (2022) 121-129. doi: 10.1007/s42864-021-00073-x
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