Citation: Shao Chenchen, Duan Hanyi, Min Yuqin, Zhang Xinghong. Diphenyl cyclopropenone-centered polymers for site-specific CO-releasing and chain dissociation[J]. Chinese Chemical Letters, ;2020, 31(1): 299-302. doi: 10.1016/j.cclet.2019.03.053 shu

Diphenyl cyclopropenone-centered polymers for site-specific CO-releasing and chain dissociation

MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027 China

minyq@zju.edu.cn

xhzhang@zju.edu.cn

Received Date: 10 March 2019
Revised Date: 25 March 2019
Accepted Date: 28 March 2019
Available Online: 28 January 2019

Figures(4)

The synthesis and stimuli-responsiveness of a diphenyl cyclopropenone (DPCP)-centered poly(methyl acrylate) (PMA) are presented. DPCP-centered PMA could release carbon monoxide (CO) upon UV light in a switched on-and-off manner. The CO-releasing process can be reported by the variations in photoluminescence spectra. In addition, DPCP moiety covalently embedded in the crosslinked polyurethane could also release CO under UV light. Of special, DPCP-centered PMA in solution was selectively dissociated at the phenol ester bond under the ultrasound, and a force-induced hydrolyzation reaction was revealed by D₂O exchanging ¹H NMR spectra. The kinetic study reveals that small quantity of water could enhance the chain scission rate. This work provides a DPCP-centered polymer for sitespecific CO-releasing and chain dissociation.
- Diphenyl cyclopropenone,
- CO-release,
- Chain dissociation,
- Ultrasound,
- UV light
1. [1]
  F.D. Jochum, P. Theato, Chem. Soc. Rev. 42(2013) 7468-7483. doi: 10.1039/C2CS35191A
2. [2]
  J. Li, C. Nagamani, J.S. Moore, Acc. Chem. Res. 48(2015) 2181-2190. doi: 10.1021/acs.accounts.5b00184
3. [3]
  M.M. Russew, S. Hecht, Adv. Mater. 22(2010) 3348-3360. doi: 10.1002/adma.200904102
4. [4]
  F. Li, C. Xie, Z. Cheng, H. Xia, Ultrason. Sonochem. 30(2016) 9-17. doi: 10.1016/j.ultsonch.2015.11.023
5. [5]
  M.A. Ayer, Y.C. Simon, C. Weder, Macromolecules 49(2016) 2917-2927. doi: 10.1021/acs.macromol.6b00418
6. [6]
  M.J. Robb, J.S. Moore, J. Am. Chem. Soc. 137(2015) 10946-10949. doi: 10.1021/jacs.5b07345
7. [7]
  A.B. Seabra, N. Durán, J. Mater. Chem. 20(2010) 1624-1637. doi: 10.1039/B912493B
8. [8]
  Y. Deng, F. Jia, S. Chen, et al., Biomaterials 187(2018) 55-65. doi: 10.1016/j.biomaterials.2018.09.043
9. [9]
  F. Ji, Y. Deng, J. Ji, Mater. Chem. Front. 2(2018) 830-834. doi: 10.1039/C8QM00013A
10. [10]
  B.E. Mann, Organometallics 31(2012) 5728-5735. doi: 10.1021/om300364a
11. [11]
  F. Zobi, Future Med. Chem. 5(2013) 175-188. doi: 10.4155/fmc.12.196
12. [12]
  N.E. Brückmann, M. Wahl, G.J. Reiß, et al., Eur. J. Inorg. Chem. 2011(2011) 4571-4577.
13. [13]
  R. Sakla, D.A. Jose, ACS Appl. Mater. Inter. 10(2018) 14214-14220. doi: 10.1021/acsami.8b03310
14. [14]
  N. Zhou, L. Peng, S. Salgado, J. Yuan, X. Wang, Angew. Chem. Int. Ed. 56(2017) 6246-6250. doi: 10.1002/anie.201611486
15. [15]
  Y. Gong, Y. Zhang, W. Xiong, et al., J. Am. Chem. Soc. 139(2017) 10649-10652. doi: 10.1021/jacs.7b06261
16. [16]
  K. Matyjaszewski, J. Xia, Chem. Rev. 101(2001) 90-146.
17. [17]
  M. Karman, E. Verde-Sesto, C. Weder, ACS Macro Lett. 7(2018) 1028-1103. doi: 10.1021/acsmacrolett.8b00520
18. [18]
  R. Tong, X. Lu, H. Xia, Chem. Comm. 50(2014) 3575-3578. doi: 10.1039/c4cc00103f
19. [19]
  S.L. Potisek, D.A. Davis, N.R. Sottos, S.R. White, J.S. Moore, J. Am. Chem. Soc.129(2007) 13808-13809. doi: 10.1021/ja076189x
20. [20]
  A. Poloukhtine, V.V. Popik, J. Org. Chem. 20(2003) 7833-7840.
21. [21]
  D.C. Church, G.I. Peterson, A.J. Boydston, ACS Macro Lett. 3(2014) 648-651. doi: 10.1021/mz5003068
22. [22]
  U. Hasegawa, A.J. van der Vlies, E. Simeoni, C. Wandrey, J.A. Hubbell, J. Am. Chem. Soc. 132(2010) 18273-18280. doi: 10.1021/ja1075025
23. [23]
  G. Dordelmann, H. Pfeiffer, A. Birkner, U. Schatzschneider, Inorg. Chem. 50(2011) 4362-4367. doi: 10.1021/ic1024197
24. [24]
  H.Y. Duan, Y.X. Wang, L.J. Wang, et al., Macromolecules 50(2017) 1353-1361. doi: 10.1021/acs.macromol.6b02370
25. [25]
  P.A.R. Glynn, B.M.E. Van Der Hoff, P.M. Reilly, J. Macromol. Sci. A 6(1972) 1653-1664. doi: 10.1080/10601327208056918
26. [26]
  S.W. Staley, T.D. Norden, W.H. Taylor, M.D. Harmony, J. Am. Chem. Soc. 109(1987) 7641-7647. doi: 10.1021/ja00259a011
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