Citation: Huixian Han, Lan Chen, Jiancheng Zhao, Haitao Yu, Yang Wang, Helian Yan, Yingxiong Wang, Zhimin Xue, Tiancheng Mu. Biomass-based Acidic Deep Eutectic Solvents for Efficient Dissolution of Lignin: Towards Performance and Mechanism Elucidation[J]. Acta Physico-Chimica Sinica, ;2023, 39(7): 221204. doi: 10.3866/PKU.WHXB202212043 shu

Biomass-based Acidic Deep Eutectic Solvents for Efficient Dissolution of Lignin: Towards Performance and Mechanism Elucidation

Huixian Han ^{1, †} ,
Lan Chen ^{1, †} ,
Jiancheng Zhao ^{2, 3} ,
Haitao Yu ¹ ,
Yang Wang ¹ ,
Helian Yan ¹ ,
Yingxiong Wang ⁴ ,
Zhimin Xue ^1,, ,
Tiancheng Mu ^5,,

1.
Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University, Beijing 100083, China
2.
Shanxi Engineering Research Center of Biorefinery, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China
3.
Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
4.
College of Chemistry, Taiyuan University of Technology, Taiyuan 030024, China
5.
Department of Chemistry, Renmin University of China, Beijing 100872, China

Corresponding author: Zhimin Xue, zmxue@bjfu.edu.cn Tiancheng Mu, tcmu@ruc.edu.cn

^†

Received Date: 27 December 2022
Revised Date: 16 January 2023
Accepted Date: 18 January 2023
Available Online: 31 January 2023
Fund Project: the National Natural Science Foundation of China 21873012the National Natural Science Foundation of China 22073112

Lignocellulose utilization has the unique feature of net-zero carbon emissions. Thus, the utilization of lignocellulose as a renewable alternative to fossil-based carbon resources is one of the most promising strategies to achieve "carbon neutrality". Lignin has been recognized as the most abundant aromatic biopolymer on Earth; hence, it could be the most promising alternative to fossil-based aromatics. The efficient dissolution of lignin is crucial for lignin upgrading, which relies on the design of innovative and robust solvents. Herein, we designed several biomass-derived acidic deep eutectic solvents (DESs) using choline chloride, betaine, and L-carnitine as hydrogen bond acceptors (HBAs), and four protic compounds as hydrogen bond donors (HBDs), namely, oxalic acid, benzoic acid, ethyl gallate, and 5-methoxysalicylic acid. The designed DESs can dissolve different types of lignin, including alkali lignin (AL), dealkaline lignin (DAL), enzymatic hydrolysis lignin (EHL), and Kraft lignin (KL). Lignin dissolution was found to be affected by the relative contents of three phenylpropanoid monomers in lignin: syringyl (S), guaiacyl (G), and p-hydroxyphenyl (H) units. More S and fewer H units in lignin could result in higher solubility. G-, S-, and H-type structural units were found in EHL, while AL, KL, and DAL had only G-type structural units. Therefore, EHL could be more easily dissolved than AL, KL, and DAL in the most developed DESs. The hydroxyl group content of the four lignin samples had a significant impact on lignin dissolution. AL (1.98 mmol·g⁻¹) and EHL (1.93 mmol·g⁻¹) had much higher contents of phenolic hydroxyl groups than DAL (0.62 mmol·g⁻¹), implying that AL and EHL had higher polarity than DAL. This resulted in different dissolution behaviors in different DESs with varying polarities. However, the sulfonate groups afforded KL with much higher polarity, thus resulting in the special dissolution behavior of KL. It is to be noted that not all cases of dissolving lignin in the developed DESs conformed to the above rules. Therefore, it is necessary to further explore the effect of the properties of the DESs on the dissolution of different lignins. Choline chloride was the preferred HBA to construct DESs with good performance and adaptability to lignin dissolution, whereas suitable acidity enabled benzoic acid and ethyl gallate to be favorable HBDs. Systematic investigation revealed that an efficient DES for lignin dissolution should possess stronger hydrogen-bonding acidity (α > 0.95) and appropriate polarity matching with the dissolved lignin. In addition, the pK_a value of the HBD and the acidity of the DESs were also efficient indices for estimating the performance of an acidic DES in dissolving lignin, and the pK_a value and acidity could be well correlated with the polarity. Generally, HBDs (e.g., BA and EG in this study) with moderate pK_a values can be employed to construct robust DESs to dissolve lignin with satisfactory solubility. Additionally, the viscosity of the DESs should have an impact on lignin dissolution, and a lower viscosity is helpful for dissolving lignin. Therefore, the better performance of the developed ChCl-based DESs than the Betaine- and L-Carnitine-based DESs was partially because of the lower viscosity of the ChCl-based DESs.
- Lignin dissolution,
- Deep eutectic solvents,
- Biomass-derived solvents,
- Hydrogen-bonding,
- Acidity,
- Polarity
1. [1]
  Tuck, C. O.; Pérez, E.; Horváth, I. T.; Sheldon, R. A.; Poliakoff, M. Science 2012, 337 (6095), 695. doi: 10.1126/science.1222566 doi: 10.1126/science.1222566
2. [2]
  Chen, Z.; Ragauskas, A.; Wan, C. Ind. Crops Prod. 2020, 147, 112241. doi: 10.1016/j.indcrop.2020.112241 doi: 10.1016/j.indcrop.2020.112241
3. [3]
  Wang, W.; Wang, Y.; Zhan, Z.; Tan, T.; Deng, W.; Zhang, Q.; Wang, Y. Acta Phys. -Chim. Sin. 2022, 38 (10), 2205032 doi: 10.3866/PKU.WHXB2022205032
4. [4]
  Zhou, H.; Jing, Y.; Wang, Y. Acta Phys. -Chim. Sin. 2022, 38 (10), 2203016 doi: 10.3866/PKU.WHXB202203016
5. [5]
  Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.; Chandra, R.; Chen, F.; Davis, M. F.; Davison, B. H.; Dixon, R. A.; Gilna, P.; Keller, M.; et al. Science 2014, 344 (6185), 1246843. doi: 10.1126/science.124684 doi: 10.1126/science.124684
6. [6]
  Sun, Z.; Fridrich, B.; De Santi, A.; Elangovan, S.; Barta, K. Chem. Rev. 2018, 118 (2), 614. doi: 10.1021/acs.chemrev.7b00588 doi: 10.1021/acs.chemrev.7b00588
7. [7]
  Luo, H.; Weeda, E. P.; Alherech, M.; Anson, C. W.; Karlen, S. D.; Cui, Y.; Foster, C. E.; Stahl, S. S. J. Am. Chem. Soc. 2021, 143 (37), 15462. doi: 10.1021/jacs.1c08635 doi: 10.1021/jacs.1c08635
8. [8]
  Adler, A.; Kumaniaev, I.; Karacic, A.; Baddigam, K. R.; Hanes, R. J.; Subbotina, E.; Bartling, A. W.; Huertas-Alonso, A. J.; Moreno, A.; Håkansson, H. Joule 2022, 6 (8), 1845. doi: 10.1016/j.joule.2022.06.021 doi: 10.1016/j.joule.2022.06.021
9. [9]
  Sun, Z.; Cheng, J.; Wang, D.; Yuan, T. -Q.; Song, G.; Barta, K. ChemSusChem 2020, 13 (19), 5199. doi: 10.1002/cssc.202001085 doi: 10.1002/cssc.202001085
10. [10]
  Rinaldi, R. Joule 2017, 1 (3), 427. doi: 10.1016/j.joule.2017.11.001 doi: 10.1016/j.joule.2017.11.001
11. [11]
  Hong, S.; Shen, X.; Xue, Z.; Sun, Z.; Yuan, T. Green Chem. 2020, 22 (21), 7219. doi: 10.1039/D0GC02439B doi: 10.1039/D0GC02439B
12. [12]
  New, E. K.; Tnah, S. K.; Voon, K. S.; Yong, K. J.; Procentese, A.; Yee Shak, K. P.; Subramonian, W.; Cheng, C. K.; Wu, T. Y. J. Environ. Manage. 2022, 307, 114385. doi: 10.1016/j.jenvman.2021.114385 doi: 10.1016/j.jenvman.2021.114385
13. [13]
  Xue, Z.; Zhao, X.; Sun, R.; Mu, T. ACS Sustain. Chem. Eng. 2016, 4 (7), 3864. doi: 10.1021/acssuschemeng.6b00639 doi: 10.1021/acssuschemeng.6b00639
14. [14]
  Zhang, H.; Bai, Y.; Yu, B.; Liu, X.; Chen, F. Green Chem. 2017, 19 (21), 5152. doi: 10.1039/C7GC01974B doi: 10.1039/C7GC01974B
15. [15]
  Yin, X.; Cai, T.; Liu, C.; Huang, C.; Wang, J.; Hu, J.; Li, N.; Jiang, J.; Wang, K. Chem. Eng. J. 2022, 437, 135408. doi: 10.1016/j.cej.2022.135408 doi: 10.1016/j.cej.2022.135408
16. [16]
  Yang, S.; Yang, X.; Meng, X.; Wang, L. Green Chem. 2022, 24 (10), 4082. doi: 10.1039/D2GC00409G doi: 10.1039/D2GC00409G
17. [17]
  Jahan, N.; Huda, M. M.; Tran, Q. X.; Rai, N. J. Phys. Chem. B 2022, 126 (31), 5752. doi: 10.1021/acs.jpcb.2c03147 doi: 10.1021/acs.jpcb.2c03147
18. [18]
  Prinsen, P.; Narani, A.; Rothenberg, G. A. ChemSusChem 2017, 10 (5), 1022. doi: 10.1002/cssc.201601608 doi: 10.1002/cssc.201601608
19. [19]
  Strassberger, Z.; Prinsen, P.; Klis, F. V. D.; Es, D. S. V.; Tanase, S.; Rothenberg, G. Green Chem. 2015, 17 (1), 325. doi: 10.1039/C4GC01143K doi: 10.1039/C4GC01143K
20. [20]
  Miao, S.; Atkin, R.; Warr, G. Green Chem. 2022, 24 (19), 7281. doi: 10.1039/D2GC02282F doi: 10.1039/D2GC02282F
21. [21]
  Zhao, W.; Wei, C.; Cui, Y.; Ye, J.; He, B.; Liu, X.; Sun, J. Chem. Eng. J. 2022, 443, 136486. doi: 10.1016/j.cej.2022.136486 doi: 10.1016/j.cej.2022.136486
22. [22]
  Sathitsuksanoh, N.; Holtman, K. M.; Yelle, D. J.; Morgan, T.; Stavila, V.; Pelton, J.; Blanch, H.; Simmons, B. A.; George, A. Green Chem. 2014, 16 (3), 1236. doi: 10.1039/C3GC42295J doi: 10.1039/C3GC42295J
23. [23]
  Liu, Q.; Zhao, X.; Yu, D.; Yu, H.; Zhang, Y.; Xue, Z.; Mu, T. Green Chem. 2019, 21 (19), 5291. doi: 10.1039/C9GC02306B doi: 10.1039/C9GC02306B
24. [24]
  Yu, H.; Xue, Z.; Shi, R.; Zhou, F.; Mu, T. Ind. Crops Prod. 2022, 184, 115049. doi: 10.1016/j.indcrop.2022.115049 doi: 10.1016/j.indcrop.2022.115049
25. [25]
  Wang, Z.; Liu, Y.; Barta, K.; Deuss, P. J. ACS Sustain. Chem. Eng. 2022, 10 (38), 12569. doi: 10.1021/acssuschemeng.2c02954 doi: 10.1021/acssuschemeng.2c02954
26. [26]
  Abbott, A. P.; Capper, G.; Davies, D. L.; Rasheed, R. K.; Tambyrajah, V. Chem. Commun. 2003, No. 1, 70. doi: 10.1039/B210714G doi: 10.1039/B210714G
27. [27]
  Smith, E. L.; Abbott, A. P.; Ryder, K. S. Chem. Rev. 2014, 114 (21), 11060. doi: 10.1021/cr300162p doi: 10.1021/cr300162p
28. [28]
  Abbott, A. P.; Boothby, D.; Capper, G.; Davies, D. L.; Rasheed, R. K. J. Am. Chem. Soc. 2004, 126 (29), 9142. doi: 10.1021/ja048266j doi: 10.1021/ja048266j
29. [29]
  Yu, D.; Xue, Z.; Mu, T. Chem. Soc. Rev. 2021, 50 (15), 8596. doi: 10.1039/D1CS90065J doi: 10.1039/D1CS90065J
30. [30]
  Xia, Q.; Liu, Y.; Meng, J.; Cheng, W.; Chen, W.; Liu, S.; Liu, Y.; Li, J.; Yu, H. Green Chem. 2018, 20 (12), 2711. doi: 10.1039/C8GC00900G doi: 10.1039/C8GC00900G
31. [31]
  Sosa, F. H. B.; Abranches, D. O.; Lopes, A. M.; Coutinho, J. A. P.; da Costa, M. C. ACS Sustain. Chem. Eng. 2020, 8 (50), 18577. doi: 10.1021/acssuschemeng.0c06655 doi: 10.1021/acssuschemeng.0c06655
32. [32]
  Malaeke, H.; Housaindokht, M. R.; Monhemi, H.; Izadyar, M. J. Mol. Liq. 2018, 263, 193. doi: 10.1016/j.molliq.2018.05.001 doi: 10.1016/j.molliq.2018.05.001
33. [33]
  Francisco, M.; Bruinhorst, A.; Kroon, M. C. Green Chem. 2012, 14 (8), 2153. doi: 10.1039/C2GC35660K doi: 10.1039/C2GC35660K
34. [34]
  Wang, Y.; Meng, X.; Jeong, K.; Li, S.; Leem, G.; Kim, K. H.; Pu, Y.; Ragauskas, A. J.; Yoo, C. G. ACS Sustain. Chem. Eng. 2020, 8 (33), 12542. doi: 10.1021/acssuschemeng.0c03533 doi: 10.1021/acssuschemeng.0c03533
35. [35]
  Meng, X.; Wang, Y.; Conte, A. J.; Zhang, S.; Ryu, J.; Wie, J. J.; Pu, Y.; Davison, B. H.; Yoo, C. G.; Ragauskas, A. J. Bioresour. Technol. 2023, 368, 128280. doi: 10.1016/j.biortech.2022.128280 doi: 10.1016/j.biortech.2022.128280
36. [36]
  Wang, Y.; Kim, K. H.; Jeong, K.; Kim, N. -K.; Yoo, C. G. Curr. Opin. Green Sustain. Chem. 2021, 27, 100396. doi: 10.1016/j.cogsc.2020.100396 doi: 10.1016/j.cogsc.2020.100396
37. [37]
  Kim, K. H.; Dutta, T.; Sun, J.; Simmons, B.; Singh, S. Green Chem. 2018, 20 (4), 809. doi: 10.1039/C7GC03029K doi: 10.1039/C7GC03029K
38. [38]
  Huang, C.; Cheng, J.; Zhan, Y.; Liu, X.; Wang, J.; Wang, Y.; Yoo, C. G.; Fang, G.; Meng, X.; Ragauskas, A. J.; et al. Bioresour. Technol. 2022, 362, 127771. doi: 10.1016/j.biortech.2022.127771 doi: 10.1016/j.biortech.2022.127771
39. [39]
  Shen, X.; Wen, J.; Mei, Q.; Chen, X.; Sun, D.; Yuan, T.; Sun, R. Green Chem. 2019, 21 (2), 275. doi: 10.1039/C8GC03064B doi: 10.1039/C8GC03064B
40. [40]
  Yu, H.; Xue, Z.; Wang, Y.; Yan, C.; Chen, L.; Mu, T. Sep. Purif. Technol. 2023, 306, 122688. doi: 10.1016/j.seppur.2022.122688 doi: 10.1016/j.seppur.2022.122688
41. [41]
  Su, H.; Yin, J.; Liu, Q.; Li, C. Acta Phys. -Chim. Sin. 2015, 31, 1468. doi: 10.3866/PKU.WHXB201506111
42. [42]
  Zhou, F.; Shi, R.; Wang, Y.; Xue, Z.; Zhang, B.; Mu, T. Phys. Chem. Chem. Phys. 2022, 24, 16973. doi: 10.1039/D2CP01816K doi: 10.1039/D2CP01816K
43. [43]
  Wang, Y.; Zhang, W.; Yang, J.; Li, M.; Peng, F.; Bian, J. Bioresour. Technol. 2022, 354, 127139. doi: 10.1016/j.biortech.2022.127139 doi: 10.1016/j.biortech.2022.127139
44. [44]
  Chen, W.; Xue, Z.; Wang, J.; Jiang, J.; Zhao, X.; Mu, T. Acta Phys. -Chim. Sin. 2018, 34 (8), 904 doi: 10.3866/PKU.WHXB201712281
45. [45]
  Ma, Q.; Wang, L.; Zhai, H.; Ren, H. Int. J. Biol. Macromol. 2021, 182, 51. doi: 10.1016/j.ijbiomac.2021.03.179 doi: 10.1016/j.ijbiomac.2021.03.179
46. [46]
  Zheng, A.; Liu, S. -B.; Deng, F. Chem. Rev. 2017, 117 (19), 12475. doi: 10.1021/acs.chemrev.7b00289 doi: 10.1021/acs.chemrev.7b00289
47. [47]
  Zhou, F.; Shi, R.; Wang, Y.; Xue, Z.; Zhang, B.; Mu, T. Phys. Chem. Chem. Phys. 2022, 24 (28), 16973. doi: 10.1039/D2CP01816K doi: 10.1039/D2CP01816K
48. [48]
  Sosa, F.; Bjelic, A.; Coutinho, J.; Costa, M.; Lopes, A. Sustain. Energy Fuels 2022, 6 (20), 4800. doi: 10.1039/D2SE00859A doi: 10.1039/D2SE00859A
49. [49]
  Hong, S.; Shen, X.; Pang, B.; Xue, Z.; Cao, X.; Wen, J.; Yuan, T. Green Chem. 2020, 22 (6), 1851. doi: 10.1039/D0GC00006J doi: 10.1039/D0GC00006J
1. [1]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
2. [2]
  Haiying Wei , Daqing Yang , Mingtao Run , Guoyan Huo . Examination and Analysis on Rationality of Experimental Design: Based on Reaction of Potassium Permanganate with Potassium Bormide. University Chemistry, 2024, 39(10): 283-288. doi: 10.12461/PKU.DXHX202404068
3. [3]
  Guodong Xu , Chengcai Sheng , Xiaomeng Zhao , Tuojiang Zhang , Zongtang Liu , Jun Dong . Reform of Comprehensive Organic Chemistry Experiments in the Context of Emerging Engineering Education: A Case Study on the Improved Preparation of Benzocaine. University Chemistry, 2024, 39(11): 286-295. doi: 10.12461/PKU.DXHX202403094
4. [4]
  Zixuan Guo , Xiaoshuai Han , Chunmei Zhang , Shuijian He , Kunming Liu , Jiapeng Hu , Weisen Yang , Shaoju Jian , Shaohua Jiang , Gaigai Duan . Activation of biomass-derived porous carbon for supercapacitors: A review. Chinese Chemical Letters, 2024, 35(7): 109007-. doi: 10.1016/j.cclet.2023.109007
5. [5]
  Songtao Cai , Liuying Wu , Yuan Li , Soham Samanta , Jinying Wang , Bing Liu , Feihu Wu , Kaitao Lai , Yingchao Liu , Junle Qu , Zhigang Yang . Intermolecular hydrogen-bonding as a robust tool toward significantly improving the photothermal conversion efficiency of a NIR-II squaraine dye. Chinese Chemical Letters, 2024, 35(4): 108599-. doi: 10.1016/j.cclet.2023.108599
6. [6]
  Wenda WANG , Jinku MA , Yuzhu WEI , Shuaishuai MA . Waste biomass-derived carbon modified porous graphite carbon nitride heterojunction for efficient photodegradation of oxytetracycline in seawater. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 809-822. doi: 10.11862/CJIC.20230353
7. [7]
  Peng Wang , Daijie Deng , Suqin Wu , Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2023.100199
8. [8]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
9. [9]
  Kezhen Qi , Shu-yuan Liu , Ruchun Li . Selective dissolution for stabilizing solid electrolyte interphase. Chinese Chemical Letters, 2024, 35(5): 109460-. doi: 10.1016/j.cclet.2023.109460
10. [10]
  Yuchen Wang , Yaoyu Liu , Xiongfei Huang , Guanjie He , Kai Yan . Fe nanoclusters anchored in biomass waste-derived porous carbon nanosheets for high-performance supercapacitor. Chinese Chemical Letters, 2024, 35(8): 109301-. doi: 10.1016/j.cclet.2023.109301
11. [11]
  Zongyi Huang , Cheng Guo , Quanxing Zheng , Hongliang Lu , Pengfei Ma , Zhengzhong Fang , Pengfei Sun , Xiaodong Yi , Zhou Chen . Efficient photocatalytic biomass-alcohol conversion with simultaneous hydrogen evolution over ultrathin 2D NiS/Ni-CdS photocatalyst. Chinese Chemical Letters, 2024, 35(7): 109580-. doi: 10.1016/j.cclet.2024.109580
12. [12]
  Xuexia Lin , Yihui Zhou , Jiafu Hong , Xiaofeng Wei , Bin Liu , Chong-Chen Wang . Facile preparation of ZIF-8/ZIF-67-derived biomass carbon composites for highly efficient electromagnetic wave absorption. Chinese Chemical Letters, 2024, 35(9): 109835-. doi: 10.1016/j.cclet.2024.109835
13. [13]
  Jiao Li , Chenyang Zhang , Chuhan Wu , Yan Liu , Xuejian Zhang , Xiao Li , Yongtao Li , Jing Sun , Zhongmin Su . Defined organic-octamolybdate crystalline superstructures derived Mo₂C@C as efficient hydrogen evolution electrocatalysts. Chinese Chemical Letters, 2024, 35(6): 108782-. doi: 10.1016/j.cclet.2023.108782
14. [14]
  Shihong Wu , Ronghui Zhou , Hang Zhao , Peng Wu . Sonoafterglow luminescence for in vivo deep-tissue imaging. Chinese Chemical Letters, 2024, 35(10): 110026-. doi: 10.1016/j.cclet.2024.110026
15. [15]
  Zhenyang Lin . A classification scheme for inorganic cluster compounds based on their electronic structures and bonding characteristics. Chinese Journal of Structural Chemistry, 2024, 43(5): 100254-100254. doi: 10.1016/j.cjsc.2024.100254
16. [16]
  Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
17. [17]
  Shengfei Dong , Ziyu Liu , Xiaoyi Yang . Hydrothermal liquefaction of biomass for jet fuel precursors: A review. Chinese Chemical Letters, 2024, 35(8): 109142-. doi: 10.1016/j.cclet.2023.109142
18. [18]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
19. [19]
  Jun-Ming Cao , Kai-Yang Zhang , Jia-Lin Yang , Zhen-Yi Gu , Xing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304
20. [20]
  Yuxiang Zhang , Jia Zhao , Sen Lin . Nitrogen doping retrofits the coordination environment of copper single-atom catalysts for deep CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100415-100415. doi: 10.1016/j.cjsc.2024.100415

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(745)
HTML views(45)

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