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
1. [1]
  Yuqing Zhu , Haohao Chen , Li Wang , Liqun Ye , Houle Zhou , Qintian Peng , Huaiyong Zhu , Yingping Huang . Piezoelectric materials for pollutants degradation: State-of-the-art accomplishments and prospects. Chinese Chemical Letters, 2024, 35(4): 108884-. doi: 10.1016/j.cclet.2023.108884
2. [2]
  Haijing Cui , Weihao Zhu , Chuning Yue , Ming Yang , Wenzhi Ren , Aiguo Wu . Recent progress of ultrasound-responsive titanium dioxide sonosensitizers in cancer treatment. Chinese Chemical Letters, 2024, 35(10): 109727-. doi: 10.1016/j.cclet.2024.109727
3. [3]
  Hui Liu , Xi Xiang , Jian-Bo Huang , Bi-Hui Zhu , Li-Yun Wang , Yuan-Jiao Tang , Fang-Xue Du , Ling Li , Feng Yan , Lang Ma , Li Qiu . Corrigendum to "Ultrasound augmenting injectable chemotaxis hydrogel for articular cartilage repair in osteoarthritis" [Chinese Chemical Letters 32 (2021) 1759-1764]. Chinese Chemical Letters, 2025, 36(2): 110562-. doi: 10.1016/j.cclet.2024.110562
4. [4]
  Yue Pan , Wenping Si , Yahao Li , Haotian Tan , Ji Liang , Feng Hou . Promoting exciton dissociation by metal ion modification in polymeric carbon nitride for photocatalysis. Chinese Chemical Letters, 2024, 35(12): 109877-. doi: 10.1016/j.cclet.2024.109877
5. [5]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
6. [6]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
7. [7]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
8. [8]
  Chaozheng He , Menghui Xi , Chenxu Zhao , Ran Wang , Ling Fu , Jinrong Huo . Highly N₂ dissociation catalyst: Ir(100) and Ir(110) surfaces. Chinese Chemical Letters, 2025, 36(3): 109671-. doi: 10.1016/j.cclet.2024.109671
9. [9]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
10. [10]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
11. [11]
  Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
12. [12]
  Yifei Zhang , Yuncong Xue , Laiwei Gao , Rui Liao , Feng Wang , Fei Wang . Merging non-covalent and covalent crosslinking: En route to single chain nanoparticles. Chinese Chemical Letters, 2024, 35(6): 109217-. doi: 10.1016/j.cclet.2023.109217
13. [13]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
14. [14]
  Fengrui Yang , Debing Wang , Xinying Zhang , Jie Zhang , Zhichao Wu , Qiaoying Wang . Synergistic effects of peroxydisulfate on UV/O₃ process for tetracycline degradation: Mechanism and pathways. Chinese Chemical Letters, 2024, 35(10): 109599-. doi: 10.1016/j.cclet.2024.109599
15. [15]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
16. [16]
  Huijuan Li , Zhu Wang , Jiagen Geng , Ruiping Song , Xiaoyin Liu , Chaochen Fu , Si Li . Current advances in UV-based advanced oxidation processes for the abatement of fluoroquinolone antibiotics in wastewater. Chinese Chemical Letters, 2025, 36(4): 110138-. doi: 10.1016/j.cclet.2024.110138
17. [17]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
18. [18]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
19. [19]
  Pu Zhang , Xiang Mao , Xuehua Dong , Ling Huang , Liling Cao , Daojiang Gao , Guohong Zou . Two UV organic-inorganic hybrid antimony-based materials with superior optical performance derived from cation-anion synergetic interactions. Chinese Chemical Letters, 2024, 35(9): 109235-. doi: 10.1016/j.cclet.2023.109235
20. [20]
  Xiaomeng Hu , Jie Yu , Lijie Sun , Linfeng Zhang , Wei Zhou , Dongpeng Yan , Xinrui Wang . Synthesis of an AVB@ZnTi-LDH composite with synergistically enhance UV blocking activity and high stability for potential application in sunscreen formulations. Chinese Chemical Letters, 2024, 35(11): 109466-. doi: 10.1016/j.cclet.2023.109466

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(996)
HTML views(38)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142