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
1. [1]
  Qingjun PAN , Zhongliang GONG , Yuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365
2. [2]
  Xin Lv , Hongxing Zhang , Kaibo Duan , Wenhui Dai , Zhihui Wen , Wei Guo , Junsheng Hao . Lighting the Way Against Cancer: Photodynamic Therapy. University Chemistry, 2024, 39(5): 70-79. doi: 10.3866/PKU.DXHX202309090
3. [3]
  Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni₃N supported Al-doped SrTiO₃: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371
4. [4]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
5. [5]
  Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
6. [6]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
7. [7]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
8. [8]
  Asif Hassan Raza , Shumail Farhan , Zhixian Yu , Yan Wu . 用于高效制氢的双S型ZnS/ZnO/CdS异质结构光催化剂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406020-. doi: 10.3866/PKU.WHXB202406020
9. [9]
  Lubing Qin , Fang Sun , Meiyin Li , Hao Fan , Likai Wang , Qing Tang , Chundong Wang , Zhenghua Tang . 原子精确的(AgPd)₂₇团簇用于硝酸盐电还原制氨：一种配体诱导策略来调控金属核. Acta Physico-Chimica Sinica, 2025, 41(1): 2403008-. doi: 10.3866/PKU.WHXB202403008
10. [10]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
11. [11]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
12. [12]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
13. [13]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
14. [14]
  Shuang Yang , Qun Wang , Caiqin Miao , Ziqi Geng , Xinran Li , Yang Li , Xiaohong Wu . Ideological and Political Education Design for Research-Oriented Experimental Course of Highly Efficient Hydrogen Production from Water Electrolysis in Aerospace Perspective. University Chemistry, 2024, 39(11): 269-277. doi: 10.12461/PKU.DXHX202403044
15. [15]
  Zijuan LI , Xuan LÜ , Jiaojiao CHEN , Haiyang ZHAO , Shuo SUN , Zhiwu ZHANG , Jianlong ZHANG , Yanling MA , Jie LI , Zixian FENG , Jiahui LIU . Synthesis of visual fluorescence emission CdSe nanocrystals based on ligand regulation. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 308-320. doi: 10.11862/CJIC.20240138
16. [16]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO₂制C₂₊产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
17. [17]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
18. [18]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
19. [19]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
20. [20]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(548)
HTML views(74)

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