Citation: LIU Xue-Fen, YU Zhe-Jian, XU Liang-Xuan, CHEN Hao, WANG Tian-Qi, YANG Peng, LUO Shu-Ping. Fluoric Phenanthrolines and Their Heteroleptic Copper Complexes: Synthesis and Application in Photocatalytic Hydrogen Evolution from Water[J]. Chinese Journal of Inorganic Chemistry, ;2020, 36(11): 2023-2030. doi: 10.11862/CJIC.2020.248 shu

Fluoric Phenanthrolines and Their Heteroleptic Copper Complexes: Synthesis and Application in Photocatalytic Hydrogen Evolution from Water

1.
Qianjiang college, Hangzhou Normal University, Hangzhou 310018, China
2.
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China

Corresponding author: YANG Peng, yangpenghz@hznu.edu.cn
Received Date: 24 December 2019
Revised Date: 29 September 2020

Figures(7)

A series of novel bidentate ligands of fluoro phenanthrolines were designed and synthesized, which could formulate a series of heteroleptic copper photosensitizers CP1~CP4 with Cu(MeCN)₄PF₆ and Xantphos as P ligand. The photosensitive activities of this copper complex were researched in water reduction system, and the turnover number (TON) of hydrogen evolution was up to 896. The absorption spectrum and fluorescence emission spectrum of the copper complexes indicated the good stability in solution. The oxidation quenching is the main quenching pathway in water reduction system, which was confirmed by the fluorescence quenching experiments. Moreover, a preliminary explanation and discussion of the structure-activity relationship and the mechanism of photocatalytic hydrogen evolution from water were carried out.
- N ligands,
- ligand design,
- heteroleptic copper complexes,
- photosensitizer,
- water splitting,
- hydrogen evolution
1. [1]
  (a) Hisatomi T, Kubota J, Domen K. Chem. Soc. Rev., 2014, 43: 7520-7535
  (b)Berardi S, Drouet S, Llobet A, et al. Chem. Soc. Rev., 2014, 43: 7501-7519
2. [2]
  Esswein A J, Nocera D G. Chem. Rev., 2007, 107(10):4022-4047 doi: 10.1021/cr050193e
3. [3]
  (a) Kalyanasundaram K, Kiwi J, Grätzel M. Helv. Chim. Acta, 1978, 61: 2720-2730
  (b)Kirch M, Lehn J M, Sauvage J P. Helv. Chim. Acta, 1979, 62: 1345-1384
  (c)Kiwi J, Gratzel M. J. Am. Chem. Soc., 1978, 100(20): 6314-6320
4. [4]
  (a) Abbotto A, Manfredi N. Dalton Trans., 2011, 40: 12421-12438
  (b)Ganga G L, Puntoriero F, Campagna S, et al. Faraday Discuss., 2012, 155: 177-190
  (c)Deponti E, Natali M. Dalton Trans., 2016, 45: 9136-914
  (d)Lin H, Liu D, Wang X X, et al. Phys. Chem. Chem. Phys., 2015, 17: 10726-10736
  (e)Na Y, Wei P C, Zhou L. Chem. Eur. J., 2016, 22: 10365-10368
5. [5]
  (a) Jiang W N, Liu J H, Li C. Inorg. Chem. Commun., 2012, 16: 81-85
  (b)Zhou R W, Manbeck G F, Brewer K J, et al. Chem. Commun., 2015, 51: 12966-12969
  (c)Mengele A K, Kaufhold S, Rau S, et al. Dalton Trans., 2016, 45: 6612-6618
6. [6]
  (a) Du P W, Knowles K, Eisenberg R. J. Am. Chem. Soc., 2008, 130(38): 12576-12577
  (b)Wang C J, Chen Y, Fu W F. Dalton Trans., 2015, 44: 14483-14493
  (c)Whang D R, Park S Y. ChemSusChem, 2015, 8: 3204-3207
  (d)Kitamoto K, Sakai K. Chem. Commun., 2016, 52: 1385-1388
7. [7]
  (a) Disalle B F, Bernhard S. J. Am. Chem. Soc., 2011, 133(31): 11819-11821
  (b)Gärtner F, Denurra S, Beller M, et al. Chem. Eur. J., 2012, 18: 3220-3225
  (c)Lu Y, McGoldrick N, Murphy F, et al. Chem. Eur. J., 2016, 22(32): 11349-11356
  (d)Xu D N, Chu Q Q, Fang B Z, et al. J. Catal., 2015, 325: 118-127
8. [8]
  Zhang X J, Jin Z L, Li Y X, et al. J. Phys. Chem. C, 2009, 113(6):2630-2635 doi: 10.1021/jp8085717
9. [9]
  (a)Probst B, Guttentag M, Rodenberg A, et al. Inorg. Chem., 2011,50(8):3404-3412
  (b)Du P, Schneider J, Li F, et al. J. Am. Chem. Soc., 2008, 130(15):5056-5058
10. [10]
  Horiuchi Y, Toyao T, Saito M, et al. J. Phys. Chem. C, 2012, 116(39):20848-20853 doi: 10.1021/jp3046005
11. [11]
  Cahiez G, Duplais C, Buendia J. Chem. Rev., 2009, 109(3):1434-1476 doi: 10.1021/cr800341a
12. [12]
  (a) Zhang W, Hong J D, Zheng J W, et al. J. Am. Chem. Soc.,2011, 133(51): 20680-20683
  (b)Lazarides T, Mccormick T, Du P, et al. J. Am. Chem. Soc., 2009, 131(26): 9192-9194
  (c)Mccormick T M, Calitree B, Orchard A, et al. J. Am. Chem. Soc., 2010, 132(44): 15480-15483
  (d)Chan S F, Chou M, Creutz C, et al. J. Am. Chem. Soc., 1981, 103(2): 369-379
13. [13]
  (a) Huang G L, Shi R, Zhu Y F. J. Mol. Catal. A: Chem., 2011, 348: 100-105
  (b)He X D, Yin L X, Li Y Q. New J. Chem., 2019, 43: 6577-6586
  (c)Gu L Y, Lei Y, Luo J, et al. ACS Appl. Mater. Interfaces., 2019, 11: 24789-24794
  (d)Yang H M, Guo M M, Hu X Y, et al. Appl. Surf. Sci., 2019, 494: 501-507
14. [14]
15. [15]
  Larsen A F, Ulven T. Org. Lett., 2011, 13(13):3546-3548 doi: 10.1021/ol201321z
16. [16]
  Zhao Y F, Schwab M G, Kiersnowski A, et al. J. Mater. Chem. C, 2016, 4:4640-4646 doi: 10.1039/C6TC00780E
17. [17]
  (a) Luo S P, Mejía E, Friedrich A, et al. Angew. Chem. Int. Ed., 2013, 52(1): 419-423
  (b)Luo S P, Chen N Y, Sun Y Y, et al. Dyes Pigm., 2016, 134: 580-585
18. [18]
  Knorn M, Rawner T, Czerwieniec R, et al. ACS Catal., 2015, 5(9):5186-5193 doi: 10.1021/acscatal.5b01071
19. [19]
  Yamamoto K, Kitamoto K, Yamauchi K, et al. Chem. Commun., 2015, 51(77):14516-14519 doi: 10.1039/C5CC03558A
20. [20]
  (a) Yu Z J, Chen H, Lennox A J J, et al. Dyes Pigm., 2019, 162: 771-775
  (b)Chen H, Xu L X, Yan L J, et al. Dyes Pigm., 2020, https://doi.org/10.1016/j.dyepig.2019.108000.
21. [21]
  (a) Krishnan C Ⅴ, Creutz C, Mahajan D, et al. Isr. J. Chem., 1982, 22: 98-106
  (b)Krishnan C Ⅴ, Sutin N. J. Am. Chem. Soc., 1981, 103: 2141-2142
22. [22]
  Kirch M, Lehn J M, Sauvage J P. Helv. Chim. Acta, 1979, 62:1345-1384 doi: 10.1002/hlca.19790620449
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沈阳化工大学材料科学与工程学院沈阳 110142