Citation: Wen-Bo LIU, Hui DANG, Wen-Ping LIU, Zong-Hua YU, Wei CAO, Kang WANG, Jian-Zhuang JIANG. Ultrathin Porphyrin-Based Covalent Organic Framework Nanosheets for Efficient Photocatalytic Oxidation of Sulfides to Sulfoxides[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(7): 1307-1314. doi: 10.11862/CJIC.2021.137 shu

Ultrathin Porphyrin-Based Covalent Organic Framework Nanosheets for Efficient Photocatalytic Oxidation of Sulfides to Sulfoxides

Wen-Bo LIU ¹ ,
Hui DANG ¹ ,
Wen-Ping LIU ¹ ,
Zong-Hua YU ¹ ,
Wei CAO ^2,, ,
Kang WANG ^1,, ,
Jian-Zhuang JIANG ^1,,

1.
Beijing Advanced Innovation Center for Materials Genome Engineering, Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry and Chemical Engineering, School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, China
2.
State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China

Corresponding author: Wei CAO, vic_cw@126.com Kang WANG, kangwang@ustb.edu.cn Jian-Zhuang JIANG, jianzhuang@ustb.edu.cn
Received Date: 30 January 2021
Revised Date: 30 March 2021

Figures(6)

Singlet oxygen (¹O₂) is an efficient and convenient oxidant for the selective oxidation of sulfides to sulfoxides. It is critical to develop efficient photosensitizers with the high ¹O₂ quantum yield. Herein, we describe the fabrication and characterization of ultrathin two-dimensional covalent organic frameworks (COFs) nanosheets (NSs), COF-367 NSs. In particular, the good dispersibility in various organic solvent and high efficiency in light harvesting of COF-367 NS endow the remarkable performance towards ¹O₂ generation upon irradiation with visible light, much better than the bulk COF-367. We also demonstrate that COF-367 NSs are an excellent heterogeneous catalyst in photocatalytic oxidation of sulfides to sulfoxides with high yield and selectivity as well as good recycling stability.
- covalent organic framework,
- nanosheets,
- singlet oxygen,
- photocatalyst,
- sulfides,
- sulfoxides
1. [1]
  Dai C N, Zhang J, Huang C P, Lei Z G. Chem. Rev. , 2017, 117: 6929-6983 doi: 10.1021/acs.chemrev.7b00030
2. [2]
  Cao M, Pang R, Wang Q Y, Han Z, Wang Z Y, Dong X Y, Li S F, Zang S Q, Mak T C W. J. Am. Chem. Soc. , 2019, 141: 14505-14509 doi: 10.1021/jacs.9b05952
3. [3]
  Li Q, Lan X W, An G Y, Ricardez-Sandoval L, Wang Z G, Bai G Y. ACS Catal. , 2020, 10: 6664-6675 doi: 10.1021/acscatal.0c00290
4. [4]
  Johnson J A, Zhang X, Reeson T C, Chen Y S, Zhang J. J. Am. Chem. Soc. , 2014, 136: 15881-15884 doi: 10.1021/ja5092672
5. [5]
  Ghogare A A, Greer A. Chem. Rev. , 2016, 116: 9994-10034 doi: 10.1021/acs.chemrev.5b00726
6. [6]
  González-Núñez M E, Mello R, Royo J, Ríos J V, Asensio G. J. Am. Chem. Soc. , 2002, 124: 9154-9163 doi: 10.1021/ja025868z
7. [7]
  Yu B, Liu A H, He L N, Li B, Diao Z F, Li Y N. Green Chem. , 2012, 14: 957-962 doi: 10.1039/c2gc00027j
8. [8]
  Liang X, Guo Z F, Wei H X, Liu X, Lv H, Xing H Z. Chem. Commun. , 2018, 54: 13002-13005 doi: 10.1039/C8CC07585A
9. [9]
  Adam W, Saha-Möller C R, Ganeshpure P A. Chem. Rev. , 2001, 101: 3499-3548 doi: 10.1021/cr000019k
10. [10]
  Baciocchi E, Giacco T D, Elisei F, Gerini M F, Guerra M, Lapi A, Liberali P. J. Am. Chem. Soc. , 2003, 125: 16444-16454 doi: 10.1021/ja037591o
11. [11]
  Li Z, Liu C, Abroshan H, Kauffman D R, Li G. ACS Catal. , 2017, 7: 3368-3374 doi: 10.1021/acscatal.7b00239
12. [12]
  Liu Y, Howarth A J, Hupp J T, Farha O K. Angew. Chem. Int. Ed. , 2015, 54: 9001-9005 doi: 10.1002/anie.201503741
13. [13]
  Mojarrad A G, Zakavi S. Catal. Sci. Technol. , 2018, 8: 768-781 doi: 10.1039/C7CY02308A
14. [14]
  Feng X N, Wang X Q, Wang H L, Wu H, Liu Z N, Zhou W, Lin Q P, Jiang J Z. ACS Appl. Mater. Interfaces, 2019, 11: 45118-45125 doi: 10.1021/acsami.9b17569
15. [15]
  Liu Y Y, Howarth A J, Vermeulen N A, Moon S Y, Hupp J T, Farha O K. Coord. Chem. Rev. , 2017, 346: 101-111 doi: 10.1016/j.ccr.2016.11.008
16. [16]
  Neveselý T, Svobodova E, Chudoba J, Sikorski M, Cibulka R. Adv. Synth. Catal. , 2016, 358: 1654-1663 doi: 10.1002/adsc.201501123
17. [17]
  Li L P, Ye B H. Inorg. Chem. , 2019, 58: 7775-7784 doi: 10.1021/acs.inorgchem.9b00220
18. [18]
  Lang X J, Hao W, Leow W R, Li S Z, Zhao J C, Chen X D. Chem. Sci. , 2015, 6: 5000-5005 doi: 10.1039/C5SC01813G
19. [19]
  Chen T H, Yuan Z B, Carver A, Zhang R. Appl. Catal. A, 2014, 478: 275-282 doi: 10.1016/j.apcata.2014.04.014
20. [20]
  Zhou X T, Ji H B. Catal. Commun. , 2014, 53: 29-32 doi: 10.1016/j.catcom.2014.04.021
21. [21]
  Kuimova M K, Balaz M, Anderson H L, Ogilby P R. J. Am. Chem. Soc. , 2009, 131: 7948-7949 doi: 10.1021/ja901237s
22. [22]
  Heydariturkmani A, Zakavi S. J. Catal. , 2018, 364: 394-405 doi: 10.1016/j.jcat.2018.06.011
23. [23]
  Jin J Q, Zhu Y C, Zhang Z H, Zhang W A. Angew. Chem. Int. Ed. , 2018, 57: 16354-16358 doi: 10.1002/anie.201808811
24. [24]
  Wang J F, Zhong Y, Wang X, Yang W T, Bai F, Zhang B B, Alarid L, Bian K F, Fan H Y. Nano Lett. , 2017, 17: 6916-6921 doi: 10.1021/acs.nanolett.7b03310
25. [25]
  Liu Y L, Pujals S, Stals P J M, Paulöhrl T, Presolski S I, Meijer E W, Albertazzi L, Palmans, A R A. J. Am. Chem. Soc. , 2018, 140: 3423-3433 doi: 10.1021/jacs.8b00122
26. [26]
  Diercks C S, Yaghi O M. Science, 2017, 355: 1585 doi: 10.1126/science.aal1585
27. [27]
  Feng X, Ding X S, Jiang D L. Chem. Soc. Rev. , 2012, 41: 6010-6022 doi: 10.1039/c2cs35157a
28. [28]
  Waller P J, Gándara F, Yaghi O M. Acc. Chem. Res. , 2015, 48: 3053-3063 doi: 10.1021/acs.accounts.5b00369
29. [29]
  Zhang C, Wu B H, Ma M Q, Wang Z K, Xu Z K. Chem. Soc. Rev. , 2019, 48: 3811-3841 doi: 10.1039/C9CS00322C
30. [30]
  Wang H, Qian C, Liu J, Zeng Y F, Wang D D, Zhou W Q, Gu L, Wu H W, Liu G F, Zhao Y L. J. Am. Chem. Soc. , 2020, 142: 4862-4871 doi: 10.1021/jacs.0c00054
31. [31]
  Dong J Q, Han X, Liu Y, Li H Y, Cui Y. Angew. Chem. Int. Ed. , 2020, 59: 13826-13837
32. [32]
  Huang W, Luo W, Li Y G. Mater. Today, 2020, 40: 160-172 doi: 10.1016/j.mattod.2020.07.003
33. [33]
  Li X, Yadav P, Loh K P. Chem. Soc. Rev. , 2020, 49: 4835-4866 doi: 10.1039/D0CS00236D
34. [34]
  Chen X, Addicoat M, Jin E Q, Zhai L P, Xu H, Huang N, Guo Z Q, Liu L L, Irle S, Jiang D L. J. Am. Chem. Soc. , 2015, 137: 3241-3247 doi: 10.1021/ja509602c
35. [35]
  Li J, Jing X C, Li Q Q, Li S W, Gao X, Feng X, Wang B. Chem. Soc. Rev. , 2020, 49: 3565-3604 doi: 10.1039/D0CS00017E
36. [36]
  Xiong J, Di J, Li H M. J. Mater. Chem. A, 2020, 8: 12928-12950. doi: 10.1039/D0TA04923A
37. [37]
  Liu W B, Li X K, Wang C M, Pan H H, Liu W P, Wang K, Zeng Q D, Wang R M, Jiang J Z. J. Am. Chem. Soc. , 2019, 141: 17431-17440 doi: 10.1021/jacs.9b09502
38. [38]
  Wang J, Li N, Xu Y X, Pang H. Chem. Eur. J. , 2020, 26: 6402-6422 doi: 10.1002/chem.202000294
39. [39]
  Dong R H, Zhang T, Feng X L. Chem. Rev. , 2018, 118: 6189-6235 doi: 10.1021/acs.chemrev.8b00056
40. [40]
  Hou Y X, Zhang X M, Sun J S, Lin S, Qi D D, Hong R R, Li D Q, Xiao X, Jiang J Z. Microporous Mesoporous Mater. , 2015, 214: 108-114 doi: 10.1016/j.micromeso.2015.05.002
41. [41]
  Ma L, Liu Y L, Liu Y, Jiang S Y, Li P, Hao Y C, Shao P P, Yin A X, Feng X, Wang B. Angew. Chem. Int. Ed. , 2019, 58: 4221-4226 doi: 10.1002/anie.201813598
42. [42]
  Liu Y Y, Buru C T, Howarth A J, Mahle J J, Buchanan J H, DeCoste J B, Hupp J T, Farha O K. J. Mater. Chem. A, 2016, 4: 13809-13813 doi: 10.1039/C6TA05903A
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