三亚吡嗪材料能源应用研究进展

doi:10.6023/cjoc202105031

摘要/Abstract

三亚吡嗪(HAT)是一种缺电子刚性平面芳香族盘状结构, 具有出色的π-π堆叠能力. 由于独特的拓扑结构和电子特征, HAT已被广泛用于构筑超分子材料、共价有机框架材料(COFs)、多孔氢键有机框架材料(HOFs)、金属有机框架材料(MOFs)等. HAT衍生物在催化、半导体、单分子磁体、水氧化、质子传导等方面也表现出巨大的应用潜能. 近年来, 由于能源需求的激增, 科学家们基于HAT衍生物在能源领域中的应用进行了大量的研究. 在跟踪了HAT衍生物在能源领域的研究进展的基础上, 综述了该领域研究的最新进展.

关键词: 三亚吡嗪(HAT)衍生物, 能源应用, 共价有机框架

Hexaazatriphenylene (HAT) is an electron deficient, rigid, planar, aromatic discotic molecule with three fused pyrazine rings and excellent π-π stacking ability. Due to its excellent topology and electronic properties, HAT has been exploited as structural motifs of supramolecules, covalent organic frameworks (COFs), porous hydrogen-bonded organic frameworks (HOFs), and metal organic frameworks (MOFs). HAT derivatives have been utilized in catalysis, semiconductors, monomolecular magnets, water oxidation, proton conduction, etc. In recent years, motivated by the increasing energy demand, scientists have intensively studied the energy applications of HAT derivatives. In this paper, the recent progress of HAT derivatives in the field of energy has been reviewed.

Key words: tripyrazine (HAT) derivatives, energy application, covalent organic framework

引用此文

崔超慧, 刘玉婷, 杜亚. 三亚吡嗪材料能源应用研究进展[J]. 有机化学, 2021, 41(11): 4167-4179.

Chaohui Cui, Yuting Liu, Ya Du. Recent Advancements of Hexaazatriphenylene-Based Materials for Energy Applications[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4167-4179.

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图/表 13

图式1. HAT的结构

Scheme 1. Structure of HAT

图1. HATN的电化学性能测试[22]

Figure 1. HATN electrochemical performance test (a) Electrode CVs; (b) chargedischarge cycles for HATN

图2. 3Q充放电机理探究[23]

Figure 2. Research on the charging and discharging mechanism of 3Q (a) The predicted lithiated structures of 3Q during the discharging process. (b) The galvanostatic charge/discharge profile of 3Q/Li cycled at a rate of 20 mA/g during the second cycle and ex-situ 15N and 13C solid-state NMR spectra, respectively, of the electrode materials cycled to different charge states, as marked on the corresponding electrochemical profiles. (c) The lithiation pathway obtained from simulations

图3. HATN-CMP的结构及电化学性能表征[25]

Figure 3. Characterization of structure and electrochemical performance of HATN-CMP (a) Schematic representation of the synthesis of hexaazatrinaphthalene CMP (HATN-CMP), the elementary pore structure and the photos of HATN-CMP electrodes and lithium batteries thus fabricated. (b) Cycle stability of HATN-CMP. (c) Capacity retention ratio of HATN-CMP (filled circle) and monomer (open circle) cathode electrodes

图4. HATNPFs的结构及它们的电化学性能表征[26]

Figure 4. Structure of HATNPFs and their electrochemical performance characterization (a) The structure and theoretical specific capacity of HATNPF1 and HATNPF2; (b) charge-discharge curve of HATNPF1; (c) comparison of cyclic stability of HATNPF1 and HATNPF2

图5. 具备低LUMO-HOMO间隙的聚合物NSHATN和N2-HATN[29-30]

Figure 5. Polymers NSHATN and N2-HATN with low LUMO-HOMO gap (a) The two-step synthesis of nanoporous sulfur-bridged hexaazatrinaphthylene polymer (NSHATN); (b) molecular structures and HOMO/LUMO energy levels of HATN and NSHATN; (c) nitrogen-linked HATN polymer (N2-HATN) and its two-step synthesis approach; (d) FT-IR spectra and UV-vis spectra of N2-HATN polymer before and after heat treatment

图6. 原位复合CNT制备高导电性的电极材料及电化学性能表征[31]

Figure 6. In-situ composite CNT to prepare highly conductive electrode materials and their electrochemical performance characterization (a) Scheme for the synthesis of 2D CCP-HATN and 2D C=N HATN from HATN-6CHO; (b) TEM images of 2D CCP-HATN and 2D CCP HATN@CNT; (c) CV curve of 2D C=N HATN, 2D CCP-HATN and 2D CCP-HATN@CNT, charge-discharge profiles of 2D CCP-HATN@CNT at different current densities

图7. 高理论比容量BQ1-COF的设计合成[32]

Figure 7. Scheme for the synthesis of BQ1-COF

图8. HAT聚合物的合成及电化学表征[33]

Figure 8. Synthesis and electrochemical characterization of HAT polymers (a) Synthetic route of PTBH-NO2 and PTBH; (b) the charge and discharge test, rate test and cycle stability test of PTBH-NO2 and PTBH in sequence

图9. TQBQ-COF的化学结构和可能的电化学氧化还原机理[38]

Figure 9. Chemical structure and possible electrochemical redox mechanism of TQBQ-COF

材料名称 (电压窗口)	电极组成及电解液		原始和稳定时容量及氧化还原利用率	循环稳定性		速率能力		文献
3Q (1.2~3.9 V)	3Q∶graphene∶PVDF (3∶6∶1) 1.0 mol/L LiTFSI-DOL/DME		0.4 mA/g: 395 mAh/g; 94% (1th) 324 mAh/g; 77% (200th)	8 A/g: 82% (2000) 80% (6000) 67% (10000)		0.4 A/g: 394 mAh/g 0.8 A/g: 334 mAh/g 1.6 A/g: 290 mAh/g 2.4 A/g: 268 mAh/g 3.2 A/g: 255 mAh/g 4 A/g: 242 mAh/g 8 A/g: 218 mAh/g		[23]
HATN/GO (1.5~4.0 V)	HATN/GO∶GO∶PVDF (5∶4∶1) 1 mol/L LiPF₆-EC/DEC		0.05 A/g: 410 mAh/g; 98% (1th) 226 mAh/g; 54% (90th)	0.5 A/g 80% (2000)		0.1 A/g: 270 mAh/g 0.2 A/g: 227 mAh/g 0.3 A/g: 211 mAh/g 0.4 A/g: 186 mAh/g 0.5 A/g: 167 mAh/g 1 A/g: 92 mAh/g		[24]
HATNTA/GO (1.5~4.0 V)	HATNTA/GO∶GO∶PVDF (5∶4∶1) 1 mol/L LiPF₆-EC/DEC		0.05 A/g: 226 mAh/g; 73% (1th) 193 mAh/g; 62% (50th)	0.5 A/g 86% (2000)		0.1 A/g: 215 mAh/g 0.2 A/g: 193 mAh/g 0.3 A/g: 183 mAh/g 0.4 A/g: 170 mAh/g 0.5 A/g: 133 mAh/g 1 A/g: 114 mAh/g		[24]
HATN-CMP (1.5~4.0 V)	HATN-CMP∶acetylene black∶PVDF (6∶3∶2) 1 mol/L LiPF₆-EC/DMC		0.1 A/g: 147 mAh/g; 71% (1th) 91 mAh/g; 43% (50th)	0.1 A/g: 62% (50)		0.1 A/g: 147 mAh/g 0.5 A/g: 65 mAh/g		[25]
HATNPF1 (1.5~4.0 V)	HATNPF1∶GO∶PVDF (4∶5∶1) LiCF₃SO₃/G4		0.05 A/g: 309 mAh/g; 74% (1th) 290 mAh/g; 69% (130th)	0.5 A/g 92% (1200)		0.1 A/g: 267 mAh/g 2 A/g: 174 mAh/g		[26]
HATNPF2 (1.5~4.0 V)	HATNPF2∶GO∶PVDF (4∶5∶1) LiCF₃SO₃/G4		0.05 A/g: 205 mAh/g; 51% (1th) 115 mAh/g; 29% (130th)	0.5 A/g 66% (1200)		0.1 A/g: 200 mAh/g 2 A/g: 112 mAh/g		[26]
NSHATN (1.5~4.0 V)	NSHATN∶GO∶PVDF (5∶4∶1) LiCF₃SO₃/G4		0.05 A/g: 320 mAh/g; 86% (1th) 234 mAh/g; 63% (100th)	0.5 A/g 83% (1500)		0.1 A/g: 270 mAh/g 8 A/g: 100 mAh/g		[29]
2D CCP-HATN @CNT (1.2~3.9 V)	2D CCP-HATN @CNT∶Super P∶Alg (8∶1∶1) 1 mol/L LiTFSI-DOL/DME		0.1 A/g: 116 mAh/g; 73% (1th) 114 mAh/g; 73% (50th)	0.5 A/g 91.2% (1000)		0.1 A/g: 116 mAh/g 1 A/g: 94 mAh/g		[31]
BQ1-COF (1.2~3.5 V)	BQ1-COF∶Super P∶PVDF (5∶4∶1) 1 mol/L LiTFSI-DOL/DME		0.039 A/g 502 mAh/g; 65% (2th)	1.54 A/g 81% (1000)		0.039 A/g: 502 mAh/g 7.73 A/g: 171mAh/g		[32]
PHATN(Na) (1.0~3.5 V)	PHATN∶Ketjenblack∶PVDF (6∶3∶1) 4 or 1 mol/L NaPF₆-DME		0.05 A/g: 220 mAh/g (2th) 205 mAh/g (100th)	2A/g 89.2% (10000) 10 A/g 83.8% (50000)		0.05 A/g: 220 mAh/g 2 A/g: 164 mAh/g 4.8 A/g: 138 mAh/g 10 A/g: 105 mAh/g		[37]
PHATN(Mg) (0.5~2.3 V)	PHATN: Ketjenblack: PTFE (6∶3∶1)		0.02 A/g: 146 mAh/g (1th) 110 mAh/g (200th)	0.02 A/g 89% (200)		0.02 A/g: 125 mAh/g 0.2 A/g: 60 mAh/g		[37]
材料名称 (电压窗口)		电极组成及电解液	原始和稳定时容量及氧化还原利用率	循环稳定性	速率能力		文献
PHATN(Al) (0.2~1.2 V)		PHATN∶Ketjenblack∶PTFE (6∶3∶1) AlCl₃-[BMIm]Cl离子液体	0.05 A/g: 145 mAh/g (1th) 92 mAh/g (100th)	0.05 A/g 87% (100)			[37]
Zn-HATN (0.2~1.2 V)		Zn-HATN∶Super P∶PVDF (6∶3.5∶0.5) 2 mol/L ZnSO₄	0.1 A/g: 405 mAh/g; 96% (1th) 320 mAh/g; 76% (150th)	5 A/g 93.3% (5000)	0.1 A/g: 370 mAh/g 20 A/g: 123 mAh/g		[41]
TQBQ-COF (Na) (1.0~3.6 V)		TQBQ-COF∶Super P∶PVDF (5∶4∶1) 1.0 mol/L NaPF₆-DEGDME	0.02 A/g: 452 mAh/g; 88% (1th) 352 mAh/g; 68% (100th)	1 A/g 96% (1000)	0.3 A/g: 278 mAh/g 1.0 A/g: 234 mAh/g 5.0 A/g: 181 mAh/g 10 A/g: 134 mAh/g		[38]
HAT550@ZTC (Na离子电容器) (0.5~2.5 V)		HAT550@ZTC∶Super P∶羧甲基纤维素钠/聚丙烯酸(8∶1∶1) 1.0 mol/L NaClO₄-EC/PC/FEC	0.1 A/g: 448 mAh/g; (1th) 343 mAh/g; (40th)	0.5 A/g 90% (1300)	0.1 A/g: 343 mAh/g 20 A/g: 124 mAh/g		[48]

材料名称 (电压窗口)	电极组成及电解液		原始和稳定时容量及氧化还原利用率	循环稳定性		速率能力		文献
3Q (1.2~3.9 V)	3Q∶graphene∶PVDF (3∶6∶1) 1.0 mol/L LiTFSI-DOL/DME		0.4 mA/g: 395 mAh/g; 94% (1th) 324 mAh/g; 77% (200th)	8 A/g: 82% (2000) 80% (6000) 67% (10000)		0.4 A/g: 394 mAh/g 0.8 A/g: 334 mAh/g 1.6 A/g: 290 mAh/g 2.4 A/g: 268 mAh/g 3.2 A/g: 255 mAh/g 4 A/g: 242 mAh/g 8 A/g: 218 mAh/g		[23]
HATN/GO (1.5~4.0 V)	HATN/GO∶GO∶PVDF (5∶4∶1) 1 mol/L LiPF₆-EC/DEC		0.05 A/g: 410 mAh/g; 98% (1th) 226 mAh/g; 54% (90th)	0.5 A/g 80% (2000)		0.1 A/g: 270 mAh/g 0.2 A/g: 227 mAh/g 0.3 A/g: 211 mAh/g 0.4 A/g: 186 mAh/g 0.5 A/g: 167 mAh/g 1 A/g: 92 mAh/g		[24]
HATNTA/GO (1.5~4.0 V)	HATNTA/GO∶GO∶PVDF (5∶4∶1) 1 mol/L LiPF₆-EC/DEC		0.05 A/g: 226 mAh/g; 73% (1th) 193 mAh/g; 62% (50th)	0.5 A/g 86% (2000)		0.1 A/g: 215 mAh/g 0.2 A/g: 193 mAh/g 0.3 A/g: 183 mAh/g 0.4 A/g: 170 mAh/g 0.5 A/g: 133 mAh/g 1 A/g: 114 mAh/g		[24]
HATN-CMP (1.5~4.0 V)	HATN-CMP∶acetylene black∶PVDF (6∶3∶2) 1 mol/L LiPF₆-EC/DMC		0.1 A/g: 147 mAh/g; 71% (1th) 91 mAh/g; 43% (50th)	0.1 A/g: 62% (50)		0.1 A/g: 147 mAh/g 0.5 A/g: 65 mAh/g		[25]
HATNPF1 (1.5~4.0 V)	HATNPF1∶GO∶PVDF (4∶5∶1) LiCF₃SO₃/G4		0.05 A/g: 309 mAh/g; 74% (1th) 290 mAh/g; 69% (130th)	0.5 A/g 92% (1200)		0.1 A/g: 267 mAh/g 2 A/g: 174 mAh/g		[26]
HATNPF2 (1.5~4.0 V)	HATNPF2∶GO∶PVDF (4∶5∶1) LiCF₃SO₃/G4		0.05 A/g: 205 mAh/g; 51% (1th) 115 mAh/g; 29% (130th)	0.5 A/g 66% (1200)		0.1 A/g: 200 mAh/g 2 A/g: 112 mAh/g		[26]
NSHATN (1.5~4.0 V)	NSHATN∶GO∶PVDF (5∶4∶1) LiCF₃SO₃/G4		0.05 A/g: 320 mAh/g; 86% (1th) 234 mAh/g; 63% (100th)	0.5 A/g 83% (1500)		0.1 A/g: 270 mAh/g 8 A/g: 100 mAh/g		[29]
2D CCP-HATN @CNT (1.2~3.9 V)	2D CCP-HATN @CNT∶Super P∶Alg (8∶1∶1) 1 mol/L LiTFSI-DOL/DME		0.1 A/g: 116 mAh/g; 73% (1th) 114 mAh/g; 73% (50th)	0.5 A/g 91.2% (1000)		0.1 A/g: 116 mAh/g 1 A/g: 94 mAh/g		[31]
BQ1-COF (1.2~3.5 V)	BQ1-COF∶Super P∶PVDF (5∶4∶1) 1 mol/L LiTFSI-DOL/DME		0.039 A/g 502 mAh/g; 65% (2th)	1.54 A/g 81% (1000)		0.039 A/g: 502 mAh/g 7.73 A/g: 171mAh/g		[32]
PHATN(Na) (1.0~3.5 V)	PHATN∶Ketjenblack∶PVDF (6∶3∶1) 4 or 1 mol/L NaPF₆-DME		0.05 A/g: 220 mAh/g (2th) 205 mAh/g (100th)	2A/g 89.2% (10000) 10 A/g 83.8% (50000)		0.05 A/g: 220 mAh/g 2 A/g: 164 mAh/g 4.8 A/g: 138 mAh/g 10 A/g: 105 mAh/g		[37]
PHATN(Mg) (0.5~2.3 V)	PHATN: Ketjenblack: PTFE (6∶3∶1)		0.02 A/g: 146 mAh/g (1th) 110 mAh/g (200th)	0.02 A/g 89% (200)		0.02 A/g: 125 mAh/g 0.2 A/g: 60 mAh/g		[37]
材料名称 (电压窗口)		电极组成及电解液	原始和稳定时容量及氧化还原利用率	循环稳定性	速率能力		文献
PHATN(Al) (0.2~1.2 V)		PHATN∶Ketjenblack∶PTFE (6∶3∶1) AlCl₃-[BMIm]Cl离子液体	0.05 A/g: 145 mAh/g (1th) 92 mAh/g (100th)	0.05 A/g 87% (100)			[37]
Zn-HATN (0.2~1.2 V)		Zn-HATN∶Super P∶PVDF (6∶3.5∶0.5) 2 mol/L ZnSO₄	0.1 A/g: 405 mAh/g; 96% (1th) 320 mAh/g; 76% (150th)	5 A/g 93.3% (5000)	0.1 A/g: 370 mAh/g 20 A/g: 123 mAh/g		[41]
TQBQ-COF (Na) (1.0~3.6 V)		TQBQ-COF∶Super P∶PVDF (5∶4∶1) 1.0 mol/L NaPF₆-DEGDME	0.02 A/g: 452 mAh/g; 88% (1th) 352 mAh/g; 68% (100th)	1 A/g 96% (1000)	0.3 A/g: 278 mAh/g 1.0 A/g: 234 mAh/g 5.0 A/g: 181 mAh/g 10 A/g: 134 mAh/g		[38]
HAT550@ZTC (Na离子电容器) (0.5~2.5 V)		HAT550@ZTC∶Super P∶羧甲基纤维素钠/聚丙烯酸(8∶1∶1) 1.0 mol/L NaClO₄-EC/PC/FEC	0.1 A/g: 448 mAh/g; (1th) 343 mAh/g; (40th)	0.5 A/g 90% (1300)	0.1 A/g: 343 mAh/g 20 A/g: 124 mAh/g		[48]

表1. 基于HAT衍生物的有机电极的组成及电化学性能对比

Table 1. Comparison of the composition and electrochemical performance of organic electrodes based on HAT derivatives

表1. 基于HAT衍生物的有机电极的组成及电化学性能对比

Table 1. Comparison of the composition and electrochemical performance of organic electrodes based on HAT derivatives

图10. HAT衍生物用于钙钛矿太阳能电池[44-45]

Figure 10. HAT derivatives are used in perovskite solar cells (a) The structure of HATNASOC7-CS, the J-V curve comparison chart of PVSC prepared with ETM and their PCE; (b) three HAT derivative structures prepared by Li's group

图11. Aza-CMP的结构及合成[47]

Figure 11. Structure and synthesis of Aza-CMP

参考文献 50

[1]	Nasielski-Hinkens, R.; Benedek-Vamos, M.; Maetens, D.; Nasielski, J. J. Organomet. Chem. 1981, 217, 179. doi: 10.1016/S0022-328X(00)85778-2
[2]	(a) Deng, H. L.; Luo, X. S.; Li, Z. H.; Zhao, J. Y.; Huang, M. H. Chin. J. Org. Chem. 2021, 41, 624. (in Chinese) doi: 10.6023/cjoc202005070
	(邓汉林, 罗贤升, 李志华, 赵江颖, 黄木华, 有机化学, 2021, 41, 624.) doi: 10.6023/cjoc202005070
	(b) Pang, C. M.; Luo, S. H.; Hao, Z. F.; Gao, J.; Huang, Z. H.; Yu, J. H.; Yu, S. M.; Wang, Z. Y. Chin. J. Org. Chem. 2018, 38, 2606. (in Chinese) doi: 10.6023/cjoc201804009
	(庞楚明, 罗时荷, 郝志峰, 高健, 黄召昊, 余家海, 余思敏, 汪朝阳, 有机化学, 2018, 38, 2606.) doi: 10.6023/cjoc201804009
[3]	(a) Kitagawa, S.; Masaoka, S. Coord. Chem. Rev. 2003, 246, 73. doi: 10.1016/S0010-8545(03)00109-7 pmid: 26168289
	(b) Segura, J. L.; Juárez, R.; Ramos, M.; Seoane, C. Chem. Soc. Rev. 2015, 44, 6850. doi: 10.1039/c5cs00181a pmid: 26168289
	(c) Yan, X.-Y.; Lin, M.-D.; Zheng, S.-T.; Zhan, T.-G.; Zhang, X.; Zhang, K.-D.; Zhao, X. Tetrahedron Lett. 2018, 59, 592. doi: 10.1016/j.tetlet.2018.01.004 pmid: 26168289
[4]	(a) Liu, R.; von Malotki, C.; Arnold, L.; Koshino, N.; Higashimura, H.; Baumgarten, M.; Müllen, K. J. Am. Chem. Soc. 2011, 133, 10372. doi: 10.1021/ja203776f
	(b) Ibáñez, S.; Poyatos, M.; Peris, E. Chem. Commun. 2017, 53, 3733. doi: 10.1039/C7CC00525C
[5]	Ramimoghadam, D.; Gray, E. M.; Webb, C. J. Int. J. Hydrogen Energy 2016, 41, 16944. doi: 10.1016/j.ijhydene.2016.07.134
[6]	(a) Lee, J.-S. M.; Cooper, A. I. Chem. Rev. 2020, 120, 2171. doi: 10.1021/acs.chemrev.9b00399
	(b) Xu, Y.; Jin, S.; Xu, H.; Nagai, A.; Jiang, D. Chem. Soc. Rev. 2013, 42, 8012. doi: 10.1039/c3cs60160a
[7]	(a) Hisaki, I.; Suzuki, Y.; Gomez, E.; Cohen, B.; Tohnai, N.; Douhal, A. Angew. Chem., Int. Ed. 2018, 57, 12650. doi: 10.1002/anie.201805472
	(b) Hisaki, I.; Suzuki, Y.; Gomez, E.; Ji, Q.; Tohnai, N.; Nakamura, T.; Douhal, A. J. Am. Chem. Soc. 2019, 141, 2111. doi: 10.1021/jacs.8b12124
[8]	(a) Côté, A. P.; Benin, A. I.; Ockwig, N. W.; Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166. doi: 10.1126/science.1120411
	(b) Ding, S.-Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548. doi: 10.1039/C2CS35072F
	(c) Huang, Z.; Xu, Q.; Hu, X. Chin. Chem. Lett. 2020, 31, 2495. doi: 10.1016/j.cclet.2020.06.017
[9]	Meng, Z.; Aykanat, A.; Mirica, K. A. Chem. Mater. 2019, 31, 819. doi: 10.1021/acs.chemmater.8b03897
[10]	(a) Yuan, F.; Li, J.; Namuangruk, S.; Kungwan, N.; Guo, J.; Wang, C. Chem. Mater. 2017, 29, 3971. doi: 10.1021/acs.chemmater.7b00353
	(b) Tahir, N.; Wang, G.; Onyshchenko, I.; De Geyter, N.; Leus, K.; Morent, R.; Van Der Voort, P. J. Catal. 2019, 375, 242. doi: 10.1016/j.jcat.2019.06.001
	(c) Huang, H.; Zhao, Y.; Bai, Y.; Li, F.; Zhang, Y.; Chen, Y. Adv. Sci. 2020, 7, 2000012. doi: 10.1002/advs.v7.9
	(d) Xiao, R.; Tobin, J. M.; Zha, M.; Hou, Y.-L.; He, J.; Vilela, F.; Xu, Z. J. Mater. Chem. A 2017, 5, 20180. doi: 10.1039/C7TA05534J
	(e) Bai, C.; Wang, H.; Ning, F.; Fu, J.; Wei, J.; Lu, G.; Shen, Y.; Zhou, X. ChemCatChem 2020, 12, 4024. doi: 10.1002/cctc.v12.16
[11]	(a) Liu, X.-Y.; Usui, T.; Hanna, J. Chem.-Eur. J. 2014, 20, 14207. doi: 10.1002/chem.v20.44 pmid: 25744355
	(b) Mahmood, J.; Lee, E. K.; Jung, M.; Shin, D.; Jeon, I.-Y.; Jung, S.-M.; Choi, H.-J.; Seo, J.-M.; Bae, S.-Y.; Sohn, S.-D.; Park, N.; Oh, J. H.; Shin, H.-J.; Baek, J.-B. Nat. Commun. 2015, 6, 6486. doi: 10.1038/ncomms7486 pmid: 25744355
[12]	Gould, C. A.; Darago, L. E.; Gonzalez, M. I.; Demir, S.; Long, J. R. Angew. Chem., Int. Ed. 2017, 56, 10103. doi: 10.1002/anie.v56.34
[13]	Walczak, R.; Kurpil, B.; Savateev, A.; Heil, T.; Schmidt, J.; Qin, Q.; Antonietti, M.; Oschatz, M. Angew. Chem., Int. Ed. 2018, 57, 10765. doi: 10.1002/anie.v57.33
[14]	Kurpil, B.; Savateev, A.; Papaefthimiou, V.; Zafeiratos, S.; Heil, T.; Özenler, S.; Dontsova, D.; Antonietti, M. Appl. Catal., B 2017, 217, 622. doi: 10.1016/j.apcatb.2017.06.036
[15]	Poizot, P.; Gaubicher, J.; Renault, S.; Dubois, L.; Liang, Y.; Yao, Y. Chem. Rev. 2020, 120, 6490. doi: 10.1021/acs.chemrev.9b00482
[16]	Liang, Y.; Yao, Y. Joule 2018, 2, 1690. doi: 10.1016/j.joule.2018.07.008
[17]	(a) Chen, R.; Luo, R.; Huang, Y.; Wu, F.; Li, L. Adv. Sci. 2016, 3, 1600051. doi: 10.1002/advs.v3.10
	(b) Liu, J.; Zhang, J.-G.; Yang, Z.; Lemmon, J. P.; Imhoff, C.; Graff, G. L.; Li, L.; Hu, J.; Wang, C.; Xiao, J.; Xia, G.; Viswanathan, V. V.; Baskaran, S.; Sprenkle, V.; Li, X.; Shao, Y.; Schwenzer, B. Adv. Funct. Mater. 2013, 23, 929. doi: 10.1002/adfm.v23.8
[18]	Larcher, D.; Tarascon, J. M. Nat. Chem. 2015, 7, 19. doi: 10.1038/nchem.2085 pmid: 25515886
[19]	Zhang, C. M.; Huang, Z.; Yang, Y.; Wang, D.; He, D. N. Chin. J. Org. Chem. 2014, 34, 1347. (in Chinese) doi: 10.6023/cjoc201406013
	(张春明, 黄昭, 杨扬, 王丹, 何丹农, 有机化学, 2014, 34, 1347.) doi: 10.6023/cjoc201406013
[20]	Wang, R.; Okajima, T.; Kitamura, F.; Matsumoto, N.; Thiemann, T.; Mataka, S.; Ohsaka, T. J. Phys. Chem. B 2003, 107, 9452. doi: 10.1021/jp0305281
[21]	Zhu, L.; Ding, G.; Xie, L.; Cao, X.; Liu, J.; Lei, X.; Ma, J. Chem. Mater. 2019, 31, 8582. doi: 10.1021/acs.chemmater.9b03109
[22]	Takayuki, M.; Takayuki, K.; Toyonari, S.; Masaharu, S. Chem. Lett. 2011, 40, 750. doi: 10.1246/cl.2011.750
[23]	Peng, C.; Ning, G.-H.; Su, J.; Zhong, G.; Tang, W.; Tian, B.; Su, C.; Yu, D.; Zu, L.; Yang, J.; Ng, M.-F.; Hu, Y.-S.; Yang, Y.; Armand, M.; Loh, K. P. Nat. Energy 2017, 2, 17074. doi: 10.1038/nenergy.2017.74
[24]	Wang, J.; Tee, K.; Lee, Y.; Riduan, S. N.; Zhang, Y. J. Mater. Chem. A 2018, 6, 2752. doi: 10.1039/C7TA10232A
[25]	Xu, F.; Chen, X.; Tang, Z.; Wu, D.; Fu, R.; Jiang, D. Chem. Commun. 2014, 50, 4788. doi: 10.1039/C4CC01002G
[26]	Wang, J.; Chen, C. S.; Zhang, Y. ACS Sustainable Chem. Eng. 2018, 6, 1772. doi: 10.1021/acssuschemeng.7b03165
[27]	Zhang, Y.; Riduan, S. N.; Wang, J. Chem.-Eur. J. 2017, 23, 16419. doi: 10.1002/chem.v23.65
[28]	Li, Q.; Wang, H.; Wang, H.-g.; Si, Z.; Li, C.; Bai, J. ChemSusChem 2020, 13, 2449. doi: 10.1002/cssc.v13.9
[29]	Wang, J.; Lee, Y.; Tee, K.; Riduan, S. N.; Zhang, Y. Chem. Commun. 2018, 54, 7681. doi: 10.1039/C8CC03801E
[30]	Wang, J.; En, J. C. Z.; Riduan, S. N.; Zhang, Y. Chem.-Eur. J. 2020, 26, 2581. doi: 10.1002/chem.v26.12
[31]	Xu, S.; Wang, G.; Biswal, B. P.; Addicoat, M.; Paasch, S.; Sheng, W.; Zhuang, X.; Brunner, E.; Heine, T.; Berger, R.; Feng, X. Angew. Chem., Int. Ed. 2019, 58, 849. doi: 10.1002/anie.v58.3
[32]	Wu, M.; Zhao, Y.; Sun, B.; Sun, Z.; Li, C.; Han, Y.; Xu, L.; Ge, Z.; Ren, Y.; Zhang, M.; Zhang, Q.; Lu, Y.; Wang, W.; Ma, Y.; Chen, Y. Nano Energy 2020, 70, 104498. doi: 10.1016/j.nanoen.2020.104498
[33]	(a) Du, Y.; Cui, C. H.; Li, Z; Zhang, Y.; Jiang, H.; Liu, Y.CN 113292725, 2021.
	(b) Yang, Y.; Zheng, F.; Xia, G.; Lun, Z.; Chen, Q. J. Mater. Chem. A 2015, 3, 18657. doi: 10.1039/C5TA05676D
[34]	Cheng, X.-B.; Zhang, R.; Zhao, C.-Z.; Wei, F.; Zhang, J.-G.; Zhang, Q. Adv. Sci. 2016, 3, 1600051. doi: 10.1002/advs.v3.10
[35]	Mao, M.; Gao, T.; Hou, S.; Wang, F.; Chen, J.; Wei, Z.; Fan, X.; Ji, X.; Ma, J.; Wang, C. Nano Lett. 2019, 19, 6665. doi: 10.1021/acs.nanolett.9b02963
[36]	Poizot, P.; Gaubicher, J.; Renault, S.; Dubois, L.; Liang, Y.; Yao, Y. Chem. Rev. 2020, 14, 6490.
[37]	Mao, M.; Luo, C.; Pollard, T. P.; Hou, S.; Gao, T.; Fan, X.; Cui, C.; Yue, J.; Tong, Y.; Yang, G.; Deng, T.; Zhang, M.; Ma, J.; Suo, L.; Borodin, O.; Wang, C. Angew. Chem., Int. Ed. 2019, 58, 17820. doi: 10.1002/anie.v58.49
[38]	Shi, R.; Liu, L.; Lu, Y.; Wang, C.; Li, Y.; Li, L.; Yan, Z.; Chen, J. Nat. Commun. 2020, 11, 178. doi: 10.1038/s41467-019-13739-5
[39]	Liang, Y.; Jing, Y.; Gheytani, S.; Lee, K.-Y.; Liu, P.; Facchetti, A.; Yao, Y. Nat. Mater. 2017, 16, 841. doi: 10.1038/nmat4919
[40]	Wu, X.; Hong, J. J.; Shin, W.; Ma, L.; Liu, T.; Bi, X.; Yuan, Y.; Qi, Y.; Surta, T. W.; Huang, W.; Neuefeind, J.; Wu, T.; Greaney, P. A.; Lu, J.; Ji, X. Nat. Energy 2019, 4, 123. doi: 10.1038/s41560-018-0309-7
[41]	Tie, Z.; Liu, L.; Deng, S.; Zhao, D.; Niu, Z. Angew. Chem., Int. Ed. 2020, 59, 4920. doi: 10.1002/anie.v59.12
[42]	(a) Ye, H. Y.; Li, W.; Li, W. S. Chin. J. Org. Chem. 2012, 32, 266. (in Chinese) doi: 10.6023/cjoc1104062
	(叶怀英, 李文, 李维实, 有机化学, 2012, 32, 266.) doi: 10.6023/cjoc1104062
	(b) Shao, J. Y.; Zhong, Y. W. Chin. J. Org. Chem. 2021, 41, 1447. (in Chinese) doi: 10.6023/cjoc202009033
	(邵将洋, 钟羽武, 有机化学, 2021, 41, 1447.) doi: 10.6023/cjoc202009033
[43]	Choudhary, S.; Gozalvez, C.; Higelin, A.; Krossing, I.; Melle- Franco, M.; Mateo-Alonso, A. Chem.-Eur. J. 2014, 20, 1525. doi: 10.1002/chem.201304071 pmid: 24323954
[44]	Zhao, D.; Zhu, Z.; Kuo, M.-Y.; Chueh, C.-C.; Jen, A. K.-Y. Angew. Chem., Int. Ed. 2016, 55, 8999. doi: 10.1002/anie.v55.31
[45]	Zhu, R.; Li, Q.-S.; Li, Z.-S. ACS Appl. Mater. Inter. 2020, 12, 38222. doi: 10.1021/acsami.0c10996
[46]	Zhang, L. L.; Zhao, X. S. Chem. Soc. Rev. 2009, 38, 2520. doi: 10.1039/b813846j pmid: 19690733
[47]	Kou, Y.; Xu, Y.; Guo, Z.; Jiang, D. Angew. Chem., Int. Ed. 2011, 50, 8753. doi: 10.1002/anie.201103493
[48]	Yan, R.; Leus, K.; Hofmann, J. P.; Antonietti, M.; Oschatz, M. Nano Energy 2020, 67, 104240. doi: 10.1016/j.nanoen.2019.104240
[49]	Manthiram, A.; Song, B.; Li, W. Energy Stor. Mater. 2017, 6, 125.
[50]	Jerng, S. E.; Chang, B.; Shin, H.; Kim, H.; Lee, T.; Char, K.; Choi, J. W. ACS Appl. Mater. Inter. 2020, 12, 10597. doi: 10.1021/acsami.0c00643