Citation: Li Lei, Wang Juejun, Chen Mengting, Chen Yong, Xiao Wangchuan, Chen Dongyang, Lin Meijin. The impact of vertical π-extension on redox mechanisms of aromatic diimide dyes[J]. Chinese Chemical Letters, ;2019, 30(12): 2254-2258. doi: 10.1016/j.cclet.2019.05.040 shu

The impact of vertical π-extension on redox mechanisms of aromatic diimide dyes

Li Lei ^a ,
Wang Juejun ^a ,
Chen Mengting ^a ,
Chen Yong ^a,*, ,
Xiao Wangchuan ^c ,
Chen Dongyang ^b ,
Lin Meijin ^a,*,

a.
College of Chemistry, Fuzhou University, Fuzhou 350116, China
b.
College of Materials Science and Engineering, Fuzhou University, Fuzhou 350116, China
c.
School of Resources and Chemical Engineering, Sanming Institute of Fluorochemical Industry, Sanming University, Sanming 365004, China

heishh@fzu.edu.cn

meijin_lin@fzu.edu.cn

Received Date: 22 March 2019
Revised Date: 30 April 2019
Accepted Date: 21 May 2019
Available Online: 24 December 2019

Figures(6)

Aromatic diimide dyes are an attractive class of redox-active organic molecules for lithium-ion batteries, whose battery performances (stabilities, conductivities and cyclicities) are strongly dependent on the sizes of their π-systems. However, due to the different Clar's structures possessed, three vertically π-extended aromatic diimides, namely, naphthalene diimide (two one-electron reductions), perylene diimide and terrylene diimide (two one-electron reductions), exhibit different electronic redox mechanisms when served as cathode materials in organic lithium-ion batteries. Herein, we have studied carefully the different electrochemical characteristics of the three aromatic diimides through experimental and theoretical calculations. Their battery present different shape of charge/discharge curves resulting from stability of their reduction state during charge/discharge process. Terrylene diimide shows better cycle and rate capacities than those of naphthalene diimide and perylene diimide, which could be attributed to the more energies released during terrylene diimide combining with lithium ions than those of other two diimides.
- Aromatic diimides,
- Lithium-ion batteries,
- π-Systems,
- Redox mechanisms,
- Clar's structures
1. [1]
  (a) M. Armand, J.M. Tarascon, Nature 451 (2008) 652-657;
  (b) M. Li, J. Lu, Z. Chen, et al., Adv. Mater. 30 (2018) 1800561;
  (c) Y. Tang, Y. Zhang, W. Li, et al., Chem. Soc. Rev. 44 (2015) 5926-5940.
2. [2]
  (a) M. Zhu, Y. Huang, Y. Huang, et al., Adv. Funct. Mater. 26 (2016) 4481-4490;
  (b) K. Sharma, K. Pareek, R. Rohan, et al., Angew. Chem. Int. Ed. 43 (2019) 604-611;
  (c) W. Li, F. Gao, X. Wang, et al., Angew. Chem. Int. Ed. 55 (2016) 9196-9201;
  (d) H. Zhang, X. Zhang, Y. Ma, Electrochim. Acta 184 (2015) 347-355.
3. [3]
  (a) Sh. Dai, F. Zhao, Q. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 1336-1343;
  (b) Z. Zhang, Z. Yang, J. Deng, et al., Small 11 (2015) 675-680;
  (c) T.B.Song, T.Yokoyama, C.C.Stoumpos, et al., J.Am.Chem.Soc.139 (2017)836-842;
  (d) Y. Lin, Q. He, F. Zhao, et al., J. Am. Chem. Soc.138 (2016) 2973-2976;
  (e) H. Imahori, T. Umeyama, S. Ito, Acc. Chem. Res. 42 (2009) 1809-1818.
4. [4]
  (a) Zh. Song, H. Zhou, Energy Environ. Sci. 6 (2013) 2280-2301;
  (b) M.E. Bhosale, K. Krishnamoorthy, Chem. Mater. 27 (2015) 2121-2126;
  (c) I.A. Rodríguez-Pérez, Z. Jian, P.K. Waldenmaier, et al., ACS Energy Lett. 1 (2016) 719-723.
5. [5]
  (a) M.Kolek, F.Otteny, P.Schmidt, et al., EnergyEnviron.Sci.10 (2017)2334-2341;
  (b)J.Winsberg, T.Hagemann, T.Janoschka, et al., Angew.Chem.Int.Ed.55 (2016) 2-28;
  (c) T. Sun, Z.j. Li, H.g. Wang, et al., Angew. Chem.Int. Ed.55 (2016) 10662-10666.
6. [6]
  (a) L. Chen, S. Liu, L. Zhao, et al., Electrochim. Acta 258 (2017) 677-683;
  (b) W. Huang, Zh. Zhu, L. Wang, et al., Angew. Chem. Int. Ed. 52 (2013) 9162-9166;
  (c) Q. Zhao, Zh. Zhu, J. Chen, Adv. Mater. 29 (2017) 1607007;
  (d) H.g. Wang, Sh. Yuan, Zh. Sia, et al., Energy Environ. Sci. 8 (2015) 3160-3165;
  (e) H.g. Wang, X.b. Zhang, Chem. -Eur. J. 24 (2018) 18235-18245.
7. [7]
  (a) S.K.M. Nalluri, Zh. Liu, Y. Wu, et al., J. Am. Chem. Soc.138 (2016) 5968-5977;
  (b) Zh. Luo, L. Liu, Q. Zhao, et al., Angew. Chem. Int. Ed. 56 (2017) 12561-12565.
8. [8]
  (a) D. Chen, A.J. Avestro, Z. Chen, et al., Adv. Mater. 27 (2015) 2907-2912;
  (b) Ch. Wang, Y. Xu, Y. Fang, et al., J. Am. Chem. Soc. 137 (2015) 3124-3130.
9. [9]
  (a) L. Li, Y.J. Hong, D.Y. Chen, et al., Electrochim. Acta 254 (2017) 255-261;
  (b) L. Li, Y.J. Hong, D.Y. Chen, et al., Chem. -Eur. J. 23 (2017) 16612-16620;
  (c) L. Li, H.X. Gong, D.Y. Chen, et al., Chem. -Eur. J. 24 (2018) 13188-13196.
10. [10]
  (a) F. Nolde, J. Qu, Ch. Kohl, et al., Chem. -Eur. J. 11 (2005) 3959-3967;
  (b) M. Kremer, M. Kersten, Höger S, Org. Chem. Front. 5 (2018) 1825-1829.
11. [11]
  (a) L. Li, Y.J. Hong, Y. Lin, et al., Chem. Commun. 54 (2018) 11941-11944;
  (b) S. Seifert, K. Shoyama, D. Schmidt, et al., Angew. Chem. Int. Ed. 55 (2016) 6390-6395.
12. [12]
  (a) D. Wu, Z. Xie, Z. Zhou, et al., J. Mater. Chem. A 3 (2015) 19137-19143;
  (b) J.O. Oña-Ruales, Y. Ruiz-Morales, J. Phys. Chem. A 118 (2014) 12262-12273;
  (c) A.D. Zdetsis, E.N. Economou, J. Phys. Chem. C 119 (2015) 16991-17003.
13. [13]
  (a) L. Fedélé, F. Sauvage, M. Bécuwe, J. Mater. Chem. A 2 (2014) 18225-18228;
  (b) H.g. Wang, Sh. Yuan, Zh. Sia, et al., Energy Environ. Sci. 8 (2015) 3160-3165.
14. [14]
  (a) H. Ke, L. Wang, Y. Chen, et al., J. Mol. Catal. A: Chem. 385 (2014) 26-30;
  (b) M. Marchini, A. Gualandi, L. Mengozzi, et al., Phys. Chem. Chem. Phys. 20 (2018) 8071-8076;
  (c) F. Nolde, J. Qu, Ch. Kohl, et al., Chem. -Eur. J. 11 (2005) 3959-3967.
15. [15]
  (a) J. Seibt, P. Marquetand, V. Engel, et al., Chem. Phys. 328 (2006) 354-362;
  (b) M.Chen, Y.J. Bae, C.M. Mauck, et al., J. Am. Chem.Soc.140 (2018) 9184-9192.
16. [16]
  (a) S. Guha, F.S. Goodson, L.J. Corson, et al., J. Am. Chem. Soc. 134 (2012) 13679-13691;
  (b) F.S. Goodson, D.K. Panda, S. Ray, et al., Org. Biomol. Chem. 11 (2013) 4797-4803;
  (c) K. Ida, H. Sakai, K. Ohkubo, et al., J. Phys. Chem. C 118 (2014) 7710-7720.
17. [17]
  (a) Y. Wu, M. Frasconi, D.M. Gardner, et al., Angew. Chem. Int. Ed. 53 (2014) 9476-9481;
  (b) S.T. Schneebeli, M. Frasconi, Zh. Liu, et al., Angew. Chem. Int. Ed. 52 (2013) 13100-13104;
  (c) Y. Wu, R.M. Young, M. Frasconi, et al., J. Am. Chem. Soc. 137 (2015) 13236-13239.
18. [18]
  (a) Y. Ding, Y. Li, G. Yu, Chemistry 1 (2016) 790-801;
  (b) Y. Liang, P. Zhang, J. Chen, Chem. Sci. 4 (2013) 1330-1337.
19. [19]
  M. Park, D.S. Shin, J. Ryu, et al., Adv. Mater. 27 (2015) 5141-5146. doi: 10.1002/adma.201502329
20. [20]
  K.Ch. Kim, T. Liu, S.W. Lee, et al., J. Am. Chem. Soc 138 (2016) 2374-2382. doi: 10.1021/jacs.5b13279
21. [21]
  (a) D.J. Kim, K.R. Hermann, A. Prokofjevs, et al., J. Am. Chem. Soc. 139 (2017) 6635-6643;
  (b) T. Ma, Z. Pan, L. Miao, et al., Angew. Chem. Int. Ed. 57 (2018) 3158-3162.
22. [22]
  S. Fujii, T. Enoki, Angew. Chem. Int. Ed. 51 (2012) 7236-7241. doi: 10.1002/anie.201202560
1. [1]
  Mei-Chen Liu , Qing-Song Liu , Yi-Zhou Quan , Jia-Ling Yu , Gang Wu , Xiu-Li Wang , Yu-Zhong Wang . Phosphorus-silicon-integrated electrolyte additive boosts cycling performance and safety of high-voltage lithium-ion batteries. Chinese Chemical Letters, 2024, 35(8): 109123-. doi: 10.1016/j.cclet.2023.109123
2. [2]
  Guihuang Fang , Ying Liu , Yangyang Feng , Ying Pan , Hongwei Yang , Yongchuan Liu , Maoxiang Wu . Tuning the ion-dipole interactions between fluoro and carbonyl (EC) by electrolyte design for stable lithium metal batteries. Chinese Chemical Letters, 2025, 36(1): 110385-. doi: 10.1016/j.cclet.2024.110385
3. [3]
  Zhong-Hui Sun , Yu-Qi Zhang , Zhen-Yi Gu , Dong-Yang Qu , Hong-Yu Guan , Xing-Long Wu . CoPSe nanoparticles confined in nitrogen-doped dual carbon network towards high-performance lithium/potassium ion batteries. Chinese Chemical Letters, 2025, 36(1): 109590-. doi: 10.1016/j.cclet.2024.109590
4. [4]
  Xingang Kong , Yabei Su , Cuijuan Xing , Weijie Cheng , Jianfeng Huang , Lifeng Zhang , Haibo Ouyang , Qi Feng . Facile synthesis of porous TiO₂/SnO₂ nanocomposite as lithium ion battery anode with enhanced cycling stability via nanoconfinement effect. Chinese Chemical Letters, 2024, 35(11): 109428-. doi: 10.1016/j.cclet.2023.109428
5. [5]
  Hui Gu , Mingyue Gao , Kuan Shen , Tianli Zhang , Junhao Zhang , Xiangjun Zheng , Xingmei Guo , Yuanjun Liu , Fu Cao , Hongxing Gu , Qinghong Kong , Shenglin Xiong . F127 assisted fabrication of Ge/rGO/CNTs nanocomposites with three-dimensional network structure for efficient lithium storage. Chinese Chemical Letters, 2024, 35(9): 109273-. doi: 10.1016/j.cclet.2023.109273
6. [6]
  Peng Zhou , Ziang Jiang , Yang Li , Peng Xiao , Feixiang Wu . Sulphur-template method for facile manufacturing porous silicon electrodes with enhanced electrochemical performance. Chinese Chemical Letters, 2024, 35(8): 109467-. doi: 10.1016/j.cclet.2023.109467
7. [7]
  Guihuang Fang , Wei Chen , Hongwei Yang , Haisheng Fang , Chuang Yu , Maoxiang Wu . Improved performance of LiMn_0.8Fe_0.2PO₄ by addition of fluoroethylene carbonate electrolyte additive. Chinese Chemical Letters, 2024, 35(6): 108799-. doi: 10.1016/j.cclet.2023.108799
8. [8]
  Wendi Dou , Guangying Wan , Tiefeng Liu , Lin Han , Wu Zhang , Chuang Sun , Rensheng Song , Jianhui Zheng , Yujing Liu , Xinyong Tao . Conductive composite binder for recyclable LiFePO₄ cathode. Chinese Chemical Letters, 2024, 35(11): 109389-. doi: 10.1016/j.cclet.2023.109389
9. [9]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2023.100335
10. [10]
  Xin-Tong Zhao , Jin-Zhi Guo , Wen-Liang Li , Jing-Ping Zhang , Xing-Long Wu . Two-dimensional conjugated coordination polymer monolayer as anode material for lithium-ion batteries: A DFT study. Chinese Chemical Letters, 2024, 35(6): 108715-. doi: 10.1016/j.cclet.2023.108715
11. [11]
  Ya Song , Mingxia Zhou , Zhu Chen , Huali Nie , Jiao-Jing Shao , Guangmin Zhou . Integrated interconnected porous and lamellar structures realized fast ion/electron conductivity in high-performance lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(6): 109200-. doi: 10.1016/j.cclet.2023.109200
12. [12]
  Zhihong LUO , Yan SHI , Jinyu AN , Deyi ZHENG , Long LI , Quansheng OUYANG , Bin SHI , Jiaojing SHAO . Two-dimensional silica-modified polyethylene oxide solid polymer electrolyte to enhance the performance of lithium-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1005-1014. doi: 10.11862/CJIC.20230444
13. [13]
  Yun Wei , Lei Zhou , Wenbin Hu , Liming Yang , Guang Yang , Chaoqiang Wang , Hui Shi , Fei Han , Yufa Feng , Xuan Ding , Penghui Shao , Xubiao Luo . Recovery of cathode copper and ternary precursors from CuS slag derived by waste lithium-ion batteries: Process analysis and evaluation. Chinese Chemical Letters, 2024, 35(7): 109172-. doi: 10.1016/j.cclet.2023.109172
14. [14]
  Mianying Huang , Zhiguang Xu , Xiaoming Lin . Mechanistic analysis of Co2VO4/X (X = Ni, C) heterostructures as anode materials of lithium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100309-100309. doi: 10.1016/j.cjsc.2023.100309
15. [15]
  Xin Li , Ling Zhang , Yunyan Fan , Shaojing Lin , Yong Lin , Yongsheng Ying , Meijiao Hu , Haiying Gao , Xianri Xu , Zhongbiao Xia , Xinchuan Lin , Junjie Lu , Xiang Han . Carbon interconnected microsized Si film toward high energy room temperature solid-state lithium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109776-. doi: 10.1016/j.cclet.2024.109776
16. [16]
  Qi Li , Pingan Li , Zetong Liu , Jiahui Zhang , Hao Zhang , Weilai Yu , Xianluo Hu . Fabricating Micro/Nanostructured Separators and Electrode Materials by Coaxial Electrospinning for Lithium-Ion Batteries: From Fundamentals to Applications. Acta Physico-Chimica Sinica, 2024, 40(10): 2311030-. doi: 10.3866/PKU.WHXB202311030
17. [17]
  Yifeng Xu , Jiquan Liu , Bin Cui , Yan Li , Gang Xie , Ying Yang . “Xiao Li’s School Adventures: The Working Principles and Safety Risks of Lithium-ion Batteries”. University Chemistry, 2024, 39(9): 259-265. doi: 10.12461/PKU.DXHX202404009
18. [18]
  Haixia Wu , Kailu Guo . Iodized polyacrylonitrile as fast-charging anode for lithium-ion battery. Chinese Chemical Letters, 2024, 35(10): 109550-. doi: 10.1016/j.cclet.2024.109550
19. [19]
  Jia-hui Li , Jinkai Qiu , Cheng Lian . Lithium-ion rapid transport mechanism and channel design in solid electrolytes. Chinese Journal of Structural Chemistry, 2025, 44(1): 100381-100381. doi: 10.1016/j.cjsc.2024.100381
20. [20]
  Yue Qian , Zhoujia Liu , Haixin Song , Ruize Yin , Hanni Yang , Siyang Li , Weiwei Xiong , Saisai Yuan , Junhao Zhang , Huan Pang . Imide-based covalent organic framework with excellent cyclability as an anode material for lithium-ion battery. Chinese Chemical Letters, 2024, 35(6): 108785-. doi: 10.1016/j.cclet.2023.108785

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(507)
HTML views(9)

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