A simple photochemical method for surface fluorination using perfluoroketones
-
* Corresponding authors.
E-mail addresses: yanbin@tsinghua.edu.cn (Y. Huang), yangwantai@tsinghua.edu.cn (W. Yang).
Citation:
Zhiwei Zhong, Yanbin Huang, Wantai Yang. A simple photochemical method for surface fluorination using perfluoroketones[J]. Chinese Chemical Letters,
;2024, 35(5): 109339.
doi:
10.1016/j.cclet.2023.109339
L.W. McKeen, Fluorinated coatings: technology, history, and applications, in: S. Ebnesajjad (Ed.), Introduction to Fluoropolymers, William Andrew Publishing, Oxford, 2013, pp. 231–276.
M.G. Dhara, S. Banerjee, Prog. Polym. Sci. 35 (2010) 1022–1077.
doi: 10.1016/j.progpolymsci.2010.04.003
Z. Ge, X.Y. Zhang, J.B. Dai, W.H. Li, Y.J. Luo, Chin. Chem. Lett. 19 (2008) 1293–1296.
doi: 10.1016/j.cclet.2008.07.014
A. Ramirez Carnero, A. Lestido-Cardama, P. Vazquez Loureiro, et al., Foods 10 (2021) 1443.
doi: 10.3390/foods10071443
C. Hogue, Chem. Eng. News 38 (2021) 16.
C. Hogue, Chem. Eng. News 36 (2021) 28–33.
X. Wang, M. Huang, Z. Su, et al., Chin. Chem. Lett. 34 (2023) 107961.
doi: 10.1016/j.cclet.2022.107961
C. Hogue, Chem. Eng. News 46 (2019) 22–25.
R.J. Lagow, J.L. Margrave, Direct fluorination: a "new" approach to fluorine chemistry, in: S.J. Lippard (Ed.), Progress in Inorganic Chemistry, John Wiley & Sons, Hoboken, 1979, pp. 161–210.
A.P. Kharitonov, Prog. Org. Coat. 61 (2008) 192–204.
doi: 10.1016/j.porgcoat.2007.09.027
S. Kirk, M. Strobel, C.Y. Lee, et al., Plasma Process. Polym. 7 (2010) 107–122.
doi: 10.1002/ppap.200900111
H.Y. Li, L. Su, S.Y. Kuang, et al., Adv. Funct. Mater. 25 (2015) 5691–5697.
doi: 10.1002/adfm.201502318
R. Wang, C. Zhang, X. Liu, et al., Appl. Surf. Sci. 328 (2015) 509–515.
doi: 10.1016/j.apsusc.2014.12.076
M. Minarik, E. Wrzecionko, A. Minarik, et al., Coatings 9 (2019) 201.
doi: 10.3390/coatings9030201
Y.Q. Liu, Q.Q. Chen, X.L. Du, Mater. Lett. 223 (2018) 207–209.
doi: 10.1016/j.matlet.2018.04.048
Y.N. Chen, D. Chen, Y.H. Ma, W.T. Yang, J. Polym. Sci. Pol. Chem. 52 (2014) 1059–1067.
doi: 10.1002/pola.27099
S. Pan, R. Guo, W. Xu, AlChE J. 60 (2014) 2752–2756.
doi: 10.1002/aic.14517
X. Yang, M. Cui, J. Zhou, et al., ACS Appl. Bio Mater. 4 (2020) 523–532.
X. Zhao, Y. Su, W. Chen, J. Peng, Z. Jiang, J. Membr. Sci. 415–416 (2012) 824–834.
N.J. Turro, Modern Molecular Photochemistry of Organic Molecules, University Science Books, Sausalito, 2010.
F.D. Lewis, J.G. Magyar, J. Org. Chem. 37 (2002) 2102–2107.
A. Michele, D. Luft, G.E.M. Tovar, A. Southan, Polym. Chem. 13 (2022) 4273–4283.
doi: 10.1039/D2PY00443G
P. Yang, W. Yang, Chem. Rev. 113 (2013) 5547–5594.
doi: 10.1021/cr300246p
J. Xu, Y. Ma, J. Xie, F.J. Xu, W. Yang, J. Polym. Sci. Part A 49 (2011) 2755–2760.
doi: 10.1002/pola.24707
W. Yang, B. Rånby, J. Appl. Polym. Sci. 62 (1996) 533–543.
doi: 10.1002/(SICI)1097-4628(19961017)62:3<533::AID-APP11>3.0.CO;2-#
J. Deng, L. Wang, L. Liu, W. Yang, Prog. Polym. Sci. 34 (2009) 156–193.
doi: 10.1016/j.progpolymsci.2008.06.002
Q.Q. Wei, T.X. Wei, Chin. Chem. Lett. 22 (2011) 721–724.
doi: 10.1016/j.cclet.2010.11.024
J. Gustavsson, C. Segal, Characterization of a perfluorinated ketone for LIF applications, in: 46th AIAA Aerospace Sciences Meeting and Exhibit, Reno, Nevada, 2008.
H.R. Xing, S. Lu, H. Yang, H.P. Zhang, Fire 5 (2022) 50.
doi: 10.3390/fire5020050
Y. Wang, Y. Qi, C. Chen, et al., ACS Appl. Mater. Interfaces 11 (2019) 44913–44921.
doi: 10.1021/acsami.9b16274
V.E. Diyuk, A.N. Zaderko, L.M. Grishchenko, et al., Appl. Nanosci. 12 (2021) 637–650.
J. Lin, D. Yan, J. Fu, Y. Chen, H. Ou, Water Res. 186 (2020) 116360.
doi: 10.1016/j.watres.2020.116360
A. Holländer, J.E. Klemberg-Sapieha, M.R. Wertheimer, J. Polym. Sci., Part A 33 (1995) 2013–2025.
doi: 10.1002/pola.1995.080331208
A. Hollander, J.E. Klemberg-Sapieha, M.R. Wertheimer, Macromolecules 27 (1994) 2893–2895.
doi: 10.1021/ma00088a035
E. Pretsch, P. Bühlmann, M. Badertscher, I.R. spectroscopy, Structure Determination of Organic Compounds: Tables of Spectral Data, Springer, Berlin, 2009, pp. 1–67.
M.E. Diaz, M.D. Savage, R.L. Cerro, J. Colloid Interface Sci. 503 (2017) 159–167.
doi: 10.1016/j.jcis.2017.05.003
J. Wloch, A.P. Terzyk, M. Wisniewski, P. Kowalczyk, Langmuir 34 (2018) 4526–4534.
doi: 10.1021/acs.langmuir.8b00257
Z. Cao, Y.I. Hsu, A. Koizumi, et al., Polym. J. 53 (2021) 1231–1239.
doi: 10.1038/s41428-021-00544-5
I. Cisse, S. Oakes, S. Sachdev, et al., Technologies 9 (2021) 36.
doi: 10.3390/technologies9020036
D. Briggs, Surface Analysis of Polymers by XPS and Static SIMS, Cambridge University Press, Cambridge, 1998.
S. Lee, J.S. Park, T.R. Lee, Langmuir 24 (2008) 4817–4826.
doi: 10.1021/la700902h
D.A. Jackson, C.J. Young, M.D. Hurley, T.J. Wallington, S.A. Mabury, Environ. Sci. Technol. 45 (2011) 8030–8036.
doi: 10.1021/es104362g
N. Taniguchi, T.J. Wallington, M.D. Hurley, et al., J. Phys. Chem. A 107 (2003) 2674–2679.
doi: 10.1021/jp0220332
Y. Díaz-de-Mera, A. Aranda, A. Notario, et al., Phys. Chem. Chem. Phys. 17 (2015) 22991–22998.
doi: 10.1039/C5CP03527A
Y. Ren, F. Bernard, V. Daele, A. Mellouki, Environ. Sci. Technol. 53 (2019) 8862–8871.
doi: 10.1021/acs.est.9b02974
J.W.R. Dolbier, A.R. Li, J. Chem. Soc. Perkin Trans. 2 (1998) 79–82.
Huaixiang Yang , Miao-Miao Li , Aijun Zhang , Jiefei Guo , Yongqi Yu , Wei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425
Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
Yukai Tong , Zhijun Wu , Bo Zhou , Min Hu , Anpei Ye . Surface tension of single suspended aerosol microdroplets. Chinese Chemical Letters, 2024, 35(4): 109062-. doi: 10.1016/j.cclet.2023.109062
Yu He , Hao Jiang , Shaoxuan Yuan , Jiayi Lu , Qiang Sun . On-surface photo-induced dechlorination. Chinese Chemical Letters, 2024, 35(9): 109807-. doi: 10.1016/j.cclet.2024.109807
Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
Ce Liang , Qiuhui Sun , Adel Al-Salihy , Mengxin Chen , Ping Xu . Recent advances in crystal phase induced surface-enhanced Raman scattering. Chinese Chemical Letters, 2024, 35(9): 109306-. doi: 10.1016/j.cclet.2023.109306
Wenhao Chen , Jian Du , Hanbin Zhang , Hancheng Wang , Kaicheng Xu , Zhujun Gao , Jiaming Tong , Jin Wang , Junjun Xue , Ting Zhi , Longlu Wang . Surface treatment of GaN nanowires for enhanced photoelectrochemical water-splitting. Chinese Chemical Letters, 2024, 35(9): 109168-. doi: 10.1016/j.cclet.2023.109168
Guoliang Liu , Zhiqiang Liu , Anmin Zheng . Modulation of zeolite surface realizes dynamic copper species redispersion. Chinese Journal of Structural Chemistry, 2024, 43(6): 100308-100308. doi: 10.1016/j.cjsc.2024.100308
Ping Wang , Tianbao Zhang , Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328
Chenghao Ge , Peng Wang , Pei Yuan , Tai Wu , Rongjun Zhao , Rong Huang , Lin Xie , Yong Hua . Tuning hot carrier transfer dynamics by perovskite surface modification. Chinese Chemical Letters, 2024, 35(10): 109352-. doi: 10.1016/j.cclet.2023.109352
Dongpu Wu , Zheng Yang , Yuchen Xia , Lulu Wu , Yingxia Zhou , Caoyuan Niu , Puhui Xie , Xin Zheng , Zhanqi Cao . Surface controllable wettability using amphiphilic rotaxane molecular shuttles. Chinese Chemical Letters, 2025, 36(2): 110353-. doi: 10.1016/j.cclet.2024.110353
Chengde Wang , Liping Huang , Shanshan Wang , Lihao Wu , Yi Wang , Jun Dong . A distinction of gliomas at cellular and tissue level by surface-enhanced Raman scattering spectroscopy. Chinese Chemical Letters, 2024, 35(5): 109383-. doi: 10.1016/j.cclet.2023.109383
Yujuan Zhao , Zaiwang Zhao . Monolayer mesoporous nanosheets with surface asymmetry via a dual-emulsion-directed monomicelle assembly. Chinese Journal of Structural Chemistry, 2024, 43(2): 100238-100238. doi: 10.1016/j.cjsc.2024.100238