Synthesis and Properties of Donor-Acceptor Type Electrochromic Materials Based on Triphenylamine and Quinoxaline

doi:10.6023/cjoc202001027

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2513-2519.DOI: 10.6023/cjoc202001027 Previous Articles Next Articles

基于给体-受体型三苯胺喹喔啉类电致变色材料的合成及性能研究

汪文源^a,b, 陈洪进^a, 张纲^a, 张蕤^a,b, 刘建^a,b,c

a 南京林业大学化学工程学院江苏省生物质绿色燃料与化学品重点实验室南京 210037;
b 江苏省林业资源高效加工利用协同创新中心南京 210037;
c 江苏省生物质能源与材料重点实验室南京 210037

收稿日期:2020-01-18 修回日期:2020-05-21 发布日期:2020-06-10
通讯作者: 张蕤, 刘建 E-mail:liu.jian@njfu.edu.cn;zhangrui@njfu.edu.cn
基金资助:
江苏省生物质能源与材料重点实验室开放基金（No.JSBEM202014）、江苏省自然科学基金（No.BK20191385）和南京林业大学高层次（高学历）人才科研启动基金（No.GXL20180033）资助项目.

Synthesis and Properties of Donor-Acceptor Type Electrochromic Materials Based on Triphenylamine and Quinoxaline

Wang Wenyuan^a,b, Chen Hongjin^a, Zhang Gang^a, Zhang Rui^a,b, Liu Jian^a,b,c

a College of Chemical Engineering, Jiangsu Key Laboratory of Biomass-Based Green Fuels and Chemicals, Nanjing Forestry University, Nanjing 210037;
b Jiangsu Co-innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing 210037;
c Jiangsu Key Laboratory of Biomass Energy and Materials, Nanjing 210037

Received:2020-01-18 Revised:2020-05-21 Published:2020-06-10
Supported by:
Project supported by the Open Funding of Jiangsu Key Laboratory of Biomass Energy and Materials (No. JSBEM202014), the Natural Science Foundation of Jiangsu Province (No. BK20191385) and the High Level Talent Project of Nanjing Forestry University (No. GXL2018003).

1. cjoc202001027.pdf(1890KB)

Abstract

Recently, electrochromic devices based on donor-acceptor (D-A) type conjugated polymers have received great attention, owing to their fast response rate, tunable color, good cycle stability, and so on. Two novel donor-acceptor-donor (D-A-D) type monomers N-(4-(5-(4-(diphenylamino)phenyl)-2,3-dimethylquinoxalin-8-yl)phenyl)-N-phenylbenzenamine (Q1) and N-(4-(6-(4-(diphenylamino)phenyl)-1,2,3,4-tetrahydrophenazin-9-yl)phenyl)-N-phenylbenzenamine (Q2) using triphenylamine as electron donor and quinoxaline-based moiety as electron acceptors were designed, which were further electrochemical polymerized to prepare D-A type electrochromic polymers poly(N-(4-(5-(4-(diphenylamino)phenyl)-2,3-dimethyl-quinoxalin-8-yl)phenyl)-N-phenylbenzenamine) (PQ1) and poly(N-(4-(6-(4-(diphenylamino)phenyl)-1,2,3,4-tetrahydrophe-nazin-9-yl)phenyl)-N-phenylbenzenamine) (PQ2), respectively. The as-prepared D-A type polymers exhibited pale yellow in the neutral state, and multicolor change with the increase of the applied potentials. These novel electrochromic materials showed fast switch rate, good cycle stability as well as good coloration efficiency. Moreover, the highest contrast ratio of both exceeded 70% around 780 nm, which guaranteed their potential practical applications.

Key words: donor-acceptor (D-A) type, triphenylamine, quinoxaline, electrochemical polymerization, electrochromic

Cite this article

Wang Wenyuan, Chen Hongjin, Zhang Gang, Zhang Rui, Liu Jian. Synthesis and Properties of Donor-Acceptor Type Electrochromic Materials Based on Triphenylamine and Quinoxaline[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2513-2519.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wang, M.; Xing, X.; Perepichka, I. F.; Shi, Y.; Zhou, D.; Wu, P.; Meng, H. Adv. Energy Mater. 2019, 1900433.
[2] Wang, Y.; Wang, S.; Wang, X.; Zhang, W.; Zheng, W.; Zhang, Y.-M.; Zhang, S. X.-A. Nat. Mater. 2019, 18, 1335.
[3] Liu, J.; Luo, G.; Mi, S.; Zheng, J.; Xu, C. Sol. Energy Mater. Sol. Cells 2018, 177, 82.
[4] Cong, S.; Wang, Z.; Gong, W.; Chen, Z.; Lu, W.; Lombardi, J. R.; Zhao, Z. Nat. Commun. 2019, 10, 678.
[5] Yen, H.-J.; Liou, G.-S. Polym. Chem. 2018, 9, 3001.
[6] Madasamy, K.; Velayutham, D.; Suryanarayanan, V.; Kathiresan, M.; Ho, K.-C J. Mater. Chem. C 2019, 7, 4622.
[7] Ma, D.; Wang, J. Sci. China:Chem. 2017, 60, 54.
[8] Pan, J.; Wang, Y.; Zheng, R.; Wang, M.; Wan, Z.; Jia, C.; Weng, X.; Xie, J.; Deng, L. J. Mater. Chem. A 2019, 7, 13956.
[9] Li, Z.-J.; Yao, C.-J.; Zhong, Y.-W. Sci. China:Chem. 2019, 6, 1675.
[10] Radosław Banasz, R.; Wałesa-Chorab, M. Coordin. Chem. Rev. 2019, 389, 1.
[11] Wu, W.; Wang, M.; Ma, J.; Cao, Y.; Deng, Y. Adv. Electron. Mater. 2018, 4, 1800185.
[12] Li, Y.; Zhou, M.; Yang, Z.; Li, Y. J. Mater. Sci. 2018, 53, 15600.
[13] Zeng, J.; Wan, Z.; Li, H.; Liu, P.; Deng, W. Sol. Energy Mater. Sol. Cells 2018, 178, 223.
[14] Zheng, R.; Fan, Y.; Wang, Y.; Wan, Z.; Jia, C.; Weng, X.; Xie, J.; Deng, L. Electrochim. Acta 2018, 286, 296.
[15] Zhang, P.; Xing, X.; Wang, Y.; Murtaza, I.; He, Y.; Cameron, J.; Ahmed, S.; Skabara, P. J.; Meng, H. J. Mater. Chem. C 2019, 7, 9467.
[16] Meng, J.; Li, X.; Qin, M.; Pei, Y.; Yang, S.; Lan, Y.; Wang, R.; Chen, G. Org. Electron. 2017, 50, 16.
[17] Xiong, S.; Li, S.; Zhang, X.; Wang, R.; Zhang, R.; Wang, X.; Wu. B.; Gong, M.; Chu, J. J. Electron. Mater. 2018, 47, 1167.
[18] Nie, G.; Wang, L.; Liu, C. J. Mater. Chem. C 2015, 3, 11318.
[19] Lu, Q.; Zhang, X.; Cai, W.; Wang, Y.; Yang, C.; Chen, Y.; Zhang, W.; Zhang, Z.; Niu, H.; Wang, W. Sol. Energy Mater. Sol. Cells 2019, 200, 109979.
[20] Wang, M.; Wang, K.; Liu, B.; Lu, H.; Huang, M.; Yang, J. Synth. Met. 2019, 251, 15.
[21] Sun, T.-G.; Li, Z-J.; Shao, J.-Y.; Zhong, Y-W. Polymers 2019, 11, 73.
[22] Zhang, Y.; Chen, S.; Zhang, Y.; Du, H.; Zhao, J. Polymers 2019, 11, 1626.
[23] Savitha, G.; Moussallem, C.; Allain, M.; Gohier, F.; FrHre, P. Chem.-Asian J. 2017, 12, 1935.
[24] Sonmez, G.; Shen, C. K. F.; Rubin, Y.; Wudl, F. Angew. Chem., Int. Ed. 2004, 43, 1498.
[25] Teran, N. B.; Reynolds, J. R. Chem. Mater. 2017, 29, 1290.
[26] Gunbas, G. E.; Durmus, A.; Toppare, L. Adv. Mater. 2008, 20, 691.
[27] Kanazawa, K.; Uemura, S. Eur. Polym. J. 2019, 119, 322.
[28] Szeghalmi, A. V.; Erdmann, M.; Engel, V. J. Am. Chem. Soc. 2004, 126, 7834.
[29] Fang, J.; Shao, J.; Gong, Z.; Zhong, Y. Chin. J. Org. Chem. 2016, 36, 2407(in Chinese). (冯骏, 邵将洋, 龚忠亮, 钟羽武, 有机化学, 2016, 36, 2407.)
[30] Shen, J.-J.; Shao, J.-Y.; Zhu, X.; Zhong, Y.-W. Org. Lett. 2016, 18, 256.
[31] Hsiao, S. H.; Liao, W. K.; Liou, G. S. Polymers 2017, 9, 511.
[32] Blouin, N.; Michaud, A.; Leclerc, M. Adv. Mater. 2007, 19, 2295.

基于给体-受体型三苯胺喹喔啉类电致变色材料的合成及性能研究

Synthesis and Properties of Donor-Acceptor Type Electrochromic Materials Based on Triphenylamine and Quinoxaline

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Maocai Xu, Jiazhuang Tian, Yanhua Yang, Gaozhang Gou, Fumin Li, Lin Shao, Kexin Chi. Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1824-1831.
[2]	Chunsheng Li, Xiaoqi Lian, Lianfen Chen. Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1492-1498.
[3]	Sihong Chen, Qi Chen, Shihe Luo, Xiying Cao, Guoxian Yang, Xiaoqing Zeng, Zhaoyang Wang. Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 919-933.
[4]	Yali Liu, Zhen Yang, Yang Li, Yan Liu, Ping Liu. Solvent Mediated Selective C—H Bond Iodination of Pyrrolo[1,2-a]quinoxaline [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4789-4797.
[5]	Ying Shi, Fuwen Qin, Jie Wang, Yanmei Yan. One-Pot Metal-Free Synthesis of [1,2,3]triazolo[1,5-a]-quinoxalines by Sequential Ugi-3CR/Alkyne-Azide Cycloaddition Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 297-302.
[6]	Li Yang, Dong Shiyu, Qin Hongwei, Tang Bingyue, Gao Wentao, Chen Yu. A Facile Synthesis and M. tuberculosis Leucyl-tRNA Synthetase Inhi-bitory Activity of Novel 3-Arylvinylquinoxaline-2-carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2817-2826.
[7]	Zhong Keli, Zhou Lulu, Deng Longlong, Tang Lijun, Gao Xue, Liu Xiuying, Yan Xiaomei. Synthesis of Novel 7-Hydroxytetrahydroquinoxaline-6-formaldehyde Acylhydrazone Derivative and Its Recognition for Al³⁺ [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1251-1256.
[8]	Zhou Xinyun, Xie Lingchao, Wu Kaile, Tan Songting. Synthesis and Photovoltaic Properties of Organic Dyes Containing Dendritic and 3D Triphenylamine Derivatives [J]. Chin. J. Org. Chem., 2019, 39(9): 2589-2598.
[9]	Yan Jianfeng, Zhang Ruiqi, Yuan Ye, Yuan Yaofeng. 4,4'-Dimethoxy-triphenylamine Conjugated Azobenzene Photochromic Switches:Synthesis, Electrochemical and Photoisomerization Studies [J]. Chin. J. Org. Chem., 2019, 39(7): 2009-2017.
[10]	Yu Jia, Xiao Yafang, Chen Jiaxiong. Design and Synthesis of Novel Red Thermally Activated Delayed Fluorescent Molecule Based on Acenaphtho[1,2-b]quinoxaline Electron-Acceptor [J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3460-3466.
[11]	Cong Wenxia, Wang Li, Yu Fuqiang, Li Jixing. Research Process towards the Synthesis of Pyrrolo[1,2-a] quinoxaline Compounds [J]. Chin. J. Org. Chem., 2018, 38(11): 2866-2878.
[12]	Zhang Meimei, Wang Jie, Liu Jianquan, Wang Xiangshan. One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions [J]. Chin. J. Org. Chem., 2017, 37(6): 1565-1570.
[13]	Jiang Zengqiang, Zhang Jie, Tong Yao, Shi Xuesong, Miao Dazhuang, Han Shiqing. One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives through Copper-Catalyzed Cascade Reactions [J]. Chin. J. Org. Chem., 2014, 34(9): 1845-1850.
[14]	Wu Yan, Ma Longxu, Niu Tianwei, Meng Fanling, Cui Xun, Piao Huri. Synthesis and Positive Inotropic Evaluation of 2-(4-Substituted benzyl-1,4-diazepan-1-yl)-N-(5-bromoquinoxalin-6-yl)acetamides [J]. Chin. J. Org. Chem., 2012, 32(9): 1719-1724.
[15]	Mao Lijun, Tan Qinglong, Xin Guanqiong, Han Mingliang, Zhang Xuejun. Synthesis and Study of Properties for Asymmetric Triphenylamine-Zinc Phthalocyanine [J]. Chin. J. Org. Chem., 2012, 32(12): 2315-2321.