COF-based electrochromic materials and devices

Yunye Wang; Zuo Xiao; Shanxin Xiong; Liming Ding

doi:10.1088/1674-4926/43/9/090202

J. Semicond. > 2022, Volume 43?>?Issue 9?> 090202

RESEARCH HIGHLIGHTS

COF-based electrochromic materials and devices

Yunye Wang¹, Zuo Xiao², Shanxin Xiong^1, and Liming Ding^2,

+ Author Affiliations

1. College of Chemistry and Chemical Engineering, Xi’an University of Science and Technology, Xi’an 710054, China
2. Center for Excellence in Nanoscience (CAS), Key Laboratory of Nanosystem and Hierarchical Fabrication (CAS), National Center for Nanoscience and Technology, Beijing 100190, China

Author Bio:

Yunye Wang is a master student at Xi’an University of Science and Technology under the supervision of Prof. Shanxin Xiong. His current research focuses on electrochromic materials and devices.

Zuo Xiao got his BS and PhD from Peking University under the supervision of Prof. Liangbing Gan. He did postdoctoral research in Eiichi Nakamura Lab at the University of Tokyo. In March 2011, he joined Liming Ding Group at National Center for Nanoscience and Technology as an associate professor. In April 2020, he was promoted to be a full professor. His current research focuses on organic solar cells.

Shanxin Xiong got his PhD from Sichuan University in 2004 under the supervision of Prof. Qi Wang. In 2005-2011, he worked as Research Scientist in Nanyang Technological University and University of California, Los Angeles, studying electrochromic materials and their application in camouflage field. Now he is a professor in Xi’an University of Science and Technology. His research focuses on organic/inorganic electrochromic materials and devices.

Liming Ding got his PhD from University of Science and Technology of China (was a joint student at Changchun Institute of Applied Chemistry, CAS). He started his research on OSCs and PLEDs in Olle Ingan?s Lab in 1998. Later on, he worked at National Center for Polymer Research, Wright-Patterson Air Force Base and Argonne National Lab (USA). He joined Konarka as a Senior Scientist in 2008. In 2010, he joined National Center for Nanoscience and Technology as a full professor. His research focuses on innovative materials and devices. He is RSC Fellow, the nominator for Xplorer Prize, and the Associate Editor for Journal of Semiconductors.

Corresponding author: Shanxin Xiong, xiongsx@xust.edu.cn; Liming Ding, ding@nanoctr.cn

DOI: 10.1088/1674-4926/43/9/090202

References

[1]	Thakur V K, Ding G, Ma J, et al. Hybrid materials and polymer electrolytes for electrochromic device applications. Adv Mater, 2012, 24, 4071 doi: 10.1002/adma.201200213
[2]	Gu H, Ming S, Lin K, et al. Isoindigo as an electron-deficient unit for high-performance polymeric electrochromics. Electrochim Acta, 2018, 260, 772 doi: 10.1016/j.electacta.2017.12.033
[3]	Arockiam J B, Son H, Han S H, et al. Iron phthalocyanine incorporated metallo-supramolecular polymer for superior electrochromic performance with high coloration efficiency and switching stability. ACS Appl Energy Mater, 2019, 2, 8416 doi: 10.1021/acsaem.9b01022
[4]	Xie Y X, Zhao W N, Li G C, et al. A naphthalenediimide-based metal-organic framework and thin film exhibiting photochromic and electrochromic properties. Inorg Chem, 2016, 55, 549 doi: 10.1021/acs.inorgchem.5b02480
[5]	Furukawa S, Ashburne J. Greater porosity with redox reaction speeds up MOF color change. Chem, 2016, 1, 186 doi: 10.1016/j.chempr.2016.07.002
[6]	Geng K, He T, Liu R, et al. Covalent organic frameworks: design, synthesis, and functions. Chem Rev, 2020, 120, 8814 doi: 10.1021/acs.chemrev.9b00550
[7]	Cao S, Li B, Zhu R, et al. Design and synthesis of covalent organic frameworks towards energy and environment fields. Chem Eng J, 2019, 355, 602 doi: 10.1016/j.cej.2018.08.184
[8]	Chen X, Geng K, Liu R, et al. Covalent organic frameworks: chemical approaches to designer structures and built-in functions. Angew Chem Int Ed, 2020, 59, 5050 doi: 10.1002/anie.201904291
[9]	Bessinger D, Muggli K, Beetz M, et al. Fast-switching vis-IR electrochromic covalent organic frameworks. J Am Chem Soc, 2021, 143, 7351 doi: 10.1021/jacs.0c12392
[10]	Segura J L, Manche?o M J, Zamora F. Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications. Chem Soc Rev, 2016, 45, 5635 doi: 10.1039/C5CS00878F
[11]	Yang L, Guo Q, Kang H, et al. Self-controlled growth of covalent organic frameworks by repolymerization. Chem Mater, 2020, 32, 5634 doi: 10.1021/acs.chemmater.0c01140
[12]	Hao Q, Li Z J, Lu C, el al. Oriented two-dimensional covalent organic framework films for near-infrared electrochromic application. J Am Chem Soc, 2019, 141, 19831 doi: 10.1021/jacs.9b09956
[13]	Yen H J, Liou G S. Recent advances in triphenylamine-based electrochromic derivatives and polymers. Polym Chem, 2018, 9, 3001 doi: 10.1039/C8PY00367J
[14]	Xiong S, Wang Y, Wang X, et al. Schiff base type conjugated organic framework nanofibers: Solvothermal synthesis and electrochromic properties. Sol Energy Mater Sol Cells, 2020, 209, 110438 doi: 10.1016/j.solmat.2020.110438
[15]	Yu F, Liu W, Ke S W, et al. Electrochromic two-dimensional covalent organic framework with a reversible dark-to-transparent switch. Nat Commun, 2020, 11, 5534 doi: 10.1038/s41467-020-19315-6
[16]	Hao Q, Li Z J, Bai B, et al. A covalent organic framework film for three-state near-infrared electrochromism and a molecular logic gate. Angew Chem Int Ed, 2021, 133, 12606 doi: 10.1002/ange.202100870
[17]	Lv F, Xiong S, Zhang J, et al. Enhanced electrochromic properties of 2,6-diaminoanthraquinone and 1,3,5-triformylresorcinol (DAAQ-TFP) covalent organic framework/functionalized graphene oxide composites containing anthraquinone active unit. Electrochim Acta, 2021, 398, 139301 doi: 10.1016/j.electacta.2021.139301
[18]	Xiong S, Zhang Y, Zhang J, et al. Solvothermal synthesis and enhanced electrochromic properties of covalent organic framework/functionalized carbon nanotubes composites electrochromic materials with anthraquinonoid active unit. Sol Energy Mater Sol Cells, 2022, 235, 111489 doi: 10.1016/j.solmat.2021.111489

Fig. 1. (Color online) (a) Chemical structures for TAPA, TTDA, and COF_TAPA-TTDA. (b) Schematic for the electrochromic phenomenon of oriented COF_TAPA-TTDA thin film. Reprinted with permission^[12], Copyright 2019, American Chemical Society. (c) The preparation of COF_TAPA-TFPA nanofibers. Reprinted with permission^[14], Copyright 2020, Elsevier.

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Fig. 2. (Color online) (a) Schematic for the redox process of COF_TAPA-TFPA nanofibers. Reprinted with permission^[14], Copyright 2020, Elsevier. (b) Synthetic route for COF_TPBD-BTDD. Reprinted with permission^[15], Copyright 2020, Springer Nature.

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Fig. 3. (Color online) (a) Color switching of COF_TPBD-BTDD device. Reprinted with permission^[15], Copyright 2020, Springer Nature. (b) Chemical structures for TPDA, PDA, and COF_TPDA-PDA. (c) The three-state electrochromic behavior of COF_TPDA-PDA thin film. Reprinted with permission^[16], Copyright 2021, Wiley.

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Table 1. Electrochromic properties of COF-based EC materials.

EC material	λ_max (nm)	t_c/t_b (s)	Coloration efficiency (cm²/C)	?T (%)	Ref.
COF_TAPA_-TTDA	610 1300	17.5/10.5 18/13	102 152	21 41	[12]
COF_TAPA-TFPA	530	4.5/4.9	115	30	[14]
COF_TPBD-BTDD	574 730	1.8/7.2 2.6/3.5	284 246	33 12	[15]
COF_Py-ttTII	550 660 880	0.38/0.2 0.29/0.14 –	318 620 858	– – –	[9]
COF_TPDA-PDA	1050 740	1.3/0.7 3.4/1.8	320 227	52 57	[16]

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[1]	Thakur V K, Ding G, Ma J, et al. Hybrid materials and polymer electrolytes for electrochromic device applications. Adv Mater, 2012, 24, 4071 doi: 10.1002/adma.201200213
[2]	Gu H, Ming S, Lin K, et al. Isoindigo as an electron-deficient unit for high-performance polymeric electrochromics. Electrochim Acta, 2018, 260, 772 doi: 10.1016/j.electacta.2017.12.033
[3]	Arockiam J B, Son H, Han S H, et al. Iron phthalocyanine incorporated metallo-supramolecular polymer for superior electrochromic performance with high coloration efficiency and switching stability. ACS Appl Energy Mater, 2019, 2, 8416 doi: 10.1021/acsaem.9b01022
[4]	Xie Y X, Zhao W N, Li G C, et al. A naphthalenediimide-based metal-organic framework and thin film exhibiting photochromic and electrochromic properties. Inorg Chem, 2016, 55, 549 doi: 10.1021/acs.inorgchem.5b02480
[5]	Furukawa S, Ashburne J. Greater porosity with redox reaction speeds up MOF color change. Chem, 2016, 1, 186 doi: 10.1016/j.chempr.2016.07.002
[6]	Geng K, He T, Liu R, et al. Covalent organic frameworks: design, synthesis, and functions. Chem Rev, 2020, 120, 8814 doi: 10.1021/acs.chemrev.9b00550
[7]	Cao S, Li B, Zhu R, et al. Design and synthesis of covalent organic frameworks towards energy and environment fields. Chem Eng J, 2019, 355, 602 doi: 10.1016/j.cej.2018.08.184
[8]	Chen X, Geng K, Liu R, et al. Covalent organic frameworks: chemical approaches to designer structures and built-in functions. Angew Chem Int Ed, 2020, 59, 5050 doi: 10.1002/anie.201904291
[9]	Bessinger D, Muggli K, Beetz M, et al. Fast-switching vis-IR electrochromic covalent organic frameworks. J Am Chem Soc, 2021, 143, 7351 doi: 10.1021/jacs.0c12392
[10]	Segura J L, Manche?o M J, Zamora F. Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications. Chem Soc Rev, 2016, 45, 5635 doi: 10.1039/C5CS00878F
[11]	Yang L, Guo Q, Kang H, et al. Self-controlled growth of covalent organic frameworks by repolymerization. Chem Mater, 2020, 32, 5634 doi: 10.1021/acs.chemmater.0c01140
[12]	Hao Q, Li Z J, Lu C, el al. Oriented two-dimensional covalent organic framework films for near-infrared electrochromic application. J Am Chem Soc, 2019, 141, 19831 doi: 10.1021/jacs.9b09956
[13]	Yen H J, Liou G S. Recent advances in triphenylamine-based electrochromic derivatives and polymers. Polym Chem, 2018, 9, 3001 doi: 10.1039/C8PY00367J
[14]	Xiong S, Wang Y, Wang X, et al. Schiff base type conjugated organic framework nanofibers: Solvothermal synthesis and electrochromic properties. Sol Energy Mater Sol Cells, 2020, 209, 110438 doi: 10.1016/j.solmat.2020.110438
[15]	Yu F, Liu W, Ke S W, et al. Electrochromic two-dimensional covalent organic framework with a reversible dark-to-transparent switch. Nat Commun, 2020, 11, 5534 doi: 10.1038/s41467-020-19315-6
[16]	Hao Q, Li Z J, Bai B, et al. A covalent organic framework film for three-state near-infrared electrochromism and a molecular logic gate. Angew Chem Int Ed, 2021, 133, 12606 doi: 10.1002/ange.202100870
[17]	Lv F, Xiong S, Zhang J, et al. Enhanced electrochromic properties of 2,6-diaminoanthraquinone and 1,3,5-triformylresorcinol (DAAQ-TFP) covalent organic framework/functionalized graphene oxide composites containing anthraquinone active unit. Electrochim Acta, 2021, 398, 139301 doi: 10.1016/j.electacta.2021.139301
[18]	Xiong S, Zhang Y, Zhang J, et al. Solvothermal synthesis and enhanced electrochromic properties of covalent organic framework/functionalized carbon nanotubes composites electrochromic materials with anthraquinonoid active unit. Sol Energy Mater Sol Cells, 2022, 235, 111489 doi: 10.1016/j.solmat.2021.111489