Enhanced photoelectric properties and photocatalytic CO2 conversion by D-A conjugated polymerization

doi:10.16085/j.issn.1000-6613.2023-1463

Abstract

Abstract:

Herein, two anthraquinone-functionalized donor-acceptor (D-A) conjugated polymeric catalysts (AQ-TEA and AQ-TEB), were prepared via Sonogashira cross-coupling of 2,6-dibromoanthraquinone (AQ) with tris(4-ethynylphenyl)amine (TEA) and 1,3,5-triethynylbenzene (TEB), respectively. The chemical structures and morphologies of the catalysts were characterized by FTIR, XPS, XRD and TEM. The optical and electronic properties of two catalysts were investigated by solid UV/Vis diffuse reflectance spectroscopy, steady-state fluorescence spectroscopy, time-resolved fluorescence spectroscopy, and electrochemical characterization. The results indicated that AQ-TEA derived from 2,6-dibromoanthraquinone and tris(4-ethynylphenyl)amine exhibited stronger visible-light absorption and charge-transfer performance. The catalytic performance of two photocatalysts for the photoreduction of CO₂ in the presence of H₂O was studied. AQ-TEA showed better performance, with a CO production rate of 392μmol/(g·h), which was 1.8 times that of AQ-TEB. Based on the results of experiments and theoretical calculations, we deduced that the strong intramolecular charge transfer (ICT) in the conjugated polymers could promote their light absorption, photoelectric conversion and photocatalytic performance. This work provides a new insight into design and fabrication of active conjugated polymeric catalysts with high photocatalytic efficiency for solar-energy conversion.

Key words: polymers, catalyst, photochemistry, carbon dioxide

摘要：

2,6-二溴蒽醌（2,6-dibromoanthraquinone，AQ）分别与三(4-乙炔苯基)胺（tris(4-ethynylphenyl)amine，TEA）和1,3,5-三乙炔基苯（1,3,5-triethynylbenzene，TEB），通过Sonogashira偶联反应制备得到两种蒽醌功能化的给体-受体（D-A）共轭聚合物催化剂（AQ-TEA和AQ-TEB）。采用FTIR、XPS、XRD和TEM 对其化学结构和形貌进行了表征。通过固体紫外/可见漫反射光谱、稳态荧光光谱、时间分辨荧光光谱和电化学表征探究了两种催化材料的光学和电学性能。结果表明，三(4-乙炔苯基)胺与2,6-二溴蒽醌构筑的AQ-TEA表现出更强的可见光吸收和电荷转移性能。研究了两种光催化剂在H₂O环境下光还原CO₂的催化性能。特别是AQ-TEA表现出更好的光催化性能，其CO的生成速率为392μmol/(g·h)，是AQ-TEB的1.8倍。基于实验和理论计算的结果，推测共轭聚合物中强的分子内电荷转移（intramolecular charge transfer，ICT）可促进其光吸收、光电转换和光催化效率的提升。本研究为设计和制备高效的光催化活性共轭聚合物催化剂提供了新的思路。

关键词: 聚合物, 催化剂, 光化学, 二氧化碳

CLC Number:

O643.3

YU Xiaoxiao, CHAO Yanhong, LIU Haiyan, ZHU Wenshuai, LIU Zhichang. Enhanced photoelectric properties and photocatalytic CO₂ conversion by D-A conjugated polymerization[J]. Chemical Industry and Engineering Progress, 2024, 43(1): 292-301.

于笑笑, 巢艳红, 刘海燕, 朱文帅, 刘植昌. D-A共轭聚合强化光电性能及光催化CO₂转化[J]. 化工进展, 2024, 43(1): 292-301.

Figures/Tables 11

References 44

1	LI Xin, YU Jiaguo, Jaroniec Mietek, et al. Cocatalysts for selective photoreduction of CO₂ into solar fuels[J]. Chemical Reviews, 2019, 119(6): 3962-4179.
2	CHU Steven. Carbon capture and sequestration[J]. Science, 2009, 325(5948): 1599.
3	WANG Zhoujun, SONG Hui, LIU Huimin, et al. Coupling of solar energy and thermal energy for carbon dioxide reduction: Status and prospects[J]. Angewandte Chemie International Edition, 2020, 59(21): 8016-8035.
4	WANG Changli, LV Zunhang, YANG Wenxiu, et al. A rational design of functional porous frameworks for electrocatalytic CO₂ reduction reaction[J]. Chemical Society Reviews, 2023,52(4): 1382-1427.
5	HU Canyu, CHEN Xing, Jingxiang LOW, et al. Near-infrared-featured broadband CO₂ reduction with water to hydrocarbons by surface plasmon[J]. Nature Communications, 2023, 14: 221.
6	ADACHI Taiki, KITAZUMI Yuki, SHIRAI Osamu, et al. Recent progress in applications of enzymatic bioelectrocatalysis[J]. Catalysts, 2020, 10(12): 1413.
7	GERARDO Grasso, DANIELA Zane, ROBERTO Dragone. Microbial nanotechnology: Challenges and prospects for green biocatalytic synthesis of nanoscale materials for sensoristic and biomedical applications[J]. Nanomaterials, 2019, 10(1): 11.
8	YUAN Lan, QI Mingyu, TANG Zirong, et al. Coupling strategy for CO₂ valorization integrated with organic synthesis by heterogeneous photocatalysis[J]. Angewandte Chemie International Edition, 2021, 60(39): 21150-21172.
9	霍景沛, 林冲, 陈桂煌. 光催化二氧化碳还原催化体系研究进展[J]. 化学推进剂与高分子材料, 2020, 18(3): 8-14.
	HUO Jingpei, LIN Chong, CHEN Guihuang. Research progress in photocatalytic reduction catalyst system of carbon dioxide[J]. Chemical Propellants & Polymeric Materials, 2020, 18(3): 8-14.
10	GUO Zhenguo, CHEN Gui, COMETTO Claudio, et al. Selectivity control of CO versus HCOO-production in the visible-light-driven catalytic reduction of CO₂ with two cooperative metal sites[J]. Nature Catalysis, 2019, 2(9): 801-808.
11	TAKEDA Hiroyuki, COMETTO Claudio, ISHITANI Osamu, et al. Electrons, photons, protons and earth-abundant metal complexes for molecular catalysis of CO₂ reduction[J]. ACS Catalysis, 2017, 7(1): 70-88.
12	PARASTAEV Alexander, MURAVEV Valery, OSTA Elisabet Huertas, et al. Breaking structure sensitivity in CO₂ hydrogenation by tuning metal-oxide interfaces in supported cobalt nanoparticles[J]. Nature Catalysis, 2022, 5(11): 1051-1060.
13	WANG Ting, SUN Fuli, LIU Shoujie, et al. Dioxygen-enhanced CO₂ photoreduction on TiO₂ supported Cu single-atom sites[J]. Applied Catalysis B: Environmental, 2023, 325: 122339.
14	WU Dongxue, LIANG Qian, SI Honglin, et al. Self-assembly of a heterogeneous microreactor with carbon dots embedded in Ti-MOF derived ZnIn₂S₄/TiO₂ microcapsules for efficient CO₂ photoreduction[J]. Journal of Materials Chemistry A, 2022, 10(46): 24519-24528.
15	王英杰, 董辰, 谢亚勃, 等. MOF基材料绿色催化CO₂还原研究进展[J]. 北京工业大学学报, 2022, 48(3): 261-272, 305.
	WANG Yingjie, DONG Chen, XIE Yabo, et al. Research progress of CO₂ reduction catalyzed by MOF-based materials[J]. Journal of Beijing University of Technology, 2022, 48(3): 261-272, 305.
16	DAI Chunhui, LIU Bin. Conjugated polymers for visible-light-driven photocatalysis[J]. Energy & Environmental Science, 2020, 13(1): 24-52.
17	HUANG Kuan, ZHANG Jia Yin, LIU Fujian, et al. Synthesis of porous polymeric catalysts for the conversion of carbon dioxide[J]. ACS Catalysis, 2018, 8(10): 9079-9102.
18	SPRICK Reiner Sebastian, JIANG Jiaxing, BONILLO Baltasar, et al. Tunable organic photocatalysts for visible-light-driven hydrogen evolution[J]. Journal of the American Chemical Society, 2015, 137(9): 3265-3270.
19	YANG Sizhuo, HU Wenhui, ZHANG Xin, et al. 2D covalent organic frameworks as intrinsic photocatalysts for visible light-driven CO₂ reduction[J]. Journal of the American Chemical Society, 2018, 140(44): 14614-14618.
20	刘雨菲, 张蜜, 路猛, 等. 共价有机框架材料在光催化CO₂还原中的应用[J]. 化学进展, 2023, 35(3): 349-359.
	LIU Yvfei, ZHANG Mi, LU Meng, et al. Covalent organic frameworks for photocatalytic CO₂ reduction[J]. Progress in Chemistry, 2023, 35(3): 349-359.
21	WANG Shengyao, Xiao HAI, DING Xing, et al. Intermolecular cascaded π-conjugation channels for electron delivery powering CO₂ photoreduction[J]. Nature Communications, 2020, 11: 1149.
22	Surya DAS, HAZRA CHOWDHURY Ipsita, HAZRA CHOWDHURY Arpita, et al. Metal-free covalent organic framework for facile production of solar fuel via CO₂ reduction[J]. Industrial & Engineering Chemistry Research, 2022, 61(46): 17044-17056.
23	LEENAERS Pieter J, MAUFORT Arthur J L A, WIENK Martijn M, et al. Impact of π-conjugated linkers on the effective exciton binding energy of diketopyrrolopyrrole-dithienopyrrole copolymers[J]. The Journal of Physical Chemistry C, 2020, 124(50): 27403-27412.
24	YU Xiaoxiao, TIAN Shuyao, ZHANG Fengtao, et al. Tailoring the exciton binding energy of 2D conjugated polymers for powering metal-free CO₂ photoreduction[J]. ACS Sustainable Chemistry & Engineering, 2022, 10(49): 16182-16188.
25	LAN Zhian, ZHANG Guigang, CHEN Xiong, et al. Reducing the exciton binding energy of donor-acceptor-based conjugated polymers to promote charge-induced reactions[J]. Angewandte Chemie (International Ed in English), 2019, 58(30): 10236-10240.
26	CUI Lin, YU Shilong, GAO Wenqiang, et al. Tetraphenylenthene-based conjugated microporous polymer for aggregation-induced electrochemiluminescence[J]. ACS Applied Materials & Interfaces, 2020, 12(7): 7966-7973.
27	YU Fengtao, ZHU Zhiqiang, LI Chuangye, et al. A redox-active perylene-anthraquinone donor-acceptor conjugated microporous polymer with an unusual electron delocalization channel for photocatalytic reduction of uranium (‍Ⅵ) in strongly acidic solution[J]. Applied Catalysis B: Environmental, 2022, 314: 121467.
28	LUO Lianwei, MA Wenyan, DONG Peihua, et al. Synthetic control of electronic property and porosity in anthraquinone-based conjugated polymer cathodes for high-rate and long-cycle-life Na-organic batteries[J]. ACS Nano, 2022, 16(9): 14590-14599.
29	QIAN Yunyang, LI Dandan, HAN Yulan, et al. Photocatalytic molecular oxygen activation by regulating excitonic effects in covalent organic frameworks[J]. Journal of the American Chemical Society, 2020, 142(49): 20763-20771.
30	LI Xiaojiao, SUN Hong-Bin, SUN Xudong. Polysulfone grafted with anthraquinone-hydroanthraquinone redox as a flexible membrane electrode for aqueous batteries[J]. Polymer, 2021, 234: 124245.
31	KIM Wonbin, AHMAD Zubair, LEE Hong-Joon, et al. Electrochemical properties of anthraquinone-containing polymer nanocomposite by nano-level molecular ordering[J]. Polymer Chemistry, 2021, 12(42): 6154-6160.
32	RUIZ-MUELLE Ana Belén, Rafael CONTRERAS-CÁCERES, Pascual OÑA-BURGOS, et al. Polyacrylic acid polymer brushes as substrates for the incorporation of anthraquinone derivatives. Unprecedented application of decorated polymer brushes on organocatalysis[J]. Applied Surface Science, 2018, 428: 566-578.
33	GUO Shien, XIAO Yuting, JIANG Baojiang. Encapsulation of Pd nanoparticles in covalent triazine frameworks for enhanced photocatalytic CO₂ conversion[J]. ACS Sustainable Chemistry & Engineering, 2021, 9(37): 12646-12654.
34	Kyung-Lyul BAE, KIM Jinmo, Chan Kyu LIM, et al. Colloidal zinc oxide-copper(‍‍Ⅰ) oxide nanocatalysts for selective aqueous photocatalytic carbon dioxide conversion into methane[J]. Nature Communications, 2017, 8: 1156.
35	YU Xiaoxiao, GONG Ke, TIAN Shuyao, et al. A hydrophilic fully conjugated covalent organic framework for photocatalytic CO₂ reduction to CO nearly 100% using pure water[J]. Journal of Materials Chemistry A, 2023, 11(11): 5627-5635.
36	GUO Liping, NIU Yingli, XU Haitao, et al. Engineering heteroatoms with atomic precision in donor-acceptor covalent triazine frameworks to boost photocatalytic hydrogen production[J]. Journal of Materials Chemistry A, 2018, 6(40): 19775-19781.
37	WANG Congyong, ZHANG Zhicheng, ZHU Yating, et al. 2D covalent organic frameworks: From synthetic strategies to advanced optical-electrical-magnetic functionalities[J]. Advanced Materials, 2022, 34(17): e2102290.
38	ZHENG Bing, QI Feng, ZHANG Yu, et al. Over 14% efficiency single-junction organic solar cells enabled by reasonable conformation modulating in naphtho[2, 3-b: 6, 7-b']difuran based polymer[J]. Advanced Energy Materials, 2021, 11(13): 2003954.
39	BARMAN Soumitra, SINGH Ashish, RAHIMI Faruk Ahamed, et al. Metal-free catalysis: A redox-active donor-acceptor conjugated microporous polymer for selective visible-light-driven CO₂ reduction to CH₄ [J]. Journal of the American Chemical Society, 2021, 143(39): 16284-16292.
40	CHEN Bo, CHEN Wanru, WANG Miao, et al. Unravelling the multiple synergies in MOF/CMP supramolecular heterojunction for enhanced artificial photosynthesis[J]. Advanced Materials Interfaces, 2023, 10(6): 2201971.
41	WANG Lujie, WANG Ruilei, ZHANG Xiao, et al. Improved photoreduction of CO₂ with water by tuning the valence band of covalent organic frameworks[J]. ChemSusChem, 2020, 13(11): 2973-2980.
42	YE Wenqiang, WANG Yuepeng, JI Guipeng, et al. Carbazolic conjugated organic polymers for visible-light-driven CO₂Photoreduction with H₂O to CO with high efficiency and selectivity[J]. ChemSusChem, 2022, 15(16): e202200759.
43	CHOE Min Su, CHOI Sunghan, LEE Hyun Seok, et al. Sustainable carbon dioxide reduction of the P3HT polymer-sensitized TiO₂/Re(Ⅰ) photocatalyst[J]. ACS Applied Materials & Interfaces, 2022, 14(45): 50718-50730.
44	YU Zhen, XIAO Yuting, GUO Shien, et al. Visible light-driven selective reduction of CO₂ by acetylene-bridged cobalt porphyrin conjugated polymers[J]. ChemSusChem, 2022, 15(12): e202200424.

催化剂	波长/nm	添加剂	产CO效率/ μmol·g^-1·h^-1	参考文献
40NU@FNBZ	>420	H₂O	18.78	[40]
TAPBB-COF	>200, 60℃	H₂O	24.6	[41]
CB-COP-mpd	>420	H₂O	191.46	[42]
P₃HT/TiO₂/RePc226	>500	H₂O，16.7% TEOA（体积分数）	138.9	[43]
CoPor-DBBP	>400	H₂O∶MeCN∶TEA= 4∶1∶2	286.7	[44]
AQ-TEA	>300	H₂O，16.7% TEOA（体积分数）	392	本工作

催化剂	波长/nm	添加剂	产CO效率/ μmol·g^-1·h^-1	参考文献
40NU@FNBZ	>420	H₂O	18.78	[40]
TAPBB-COF	>200, 60℃	H₂O	24.6	[41]
CB-COP-mpd	>420	H₂O	191.46	[42]
P₃HT/TiO₂/RePc226	>500	H₂O，16.7% TEOA（体积分数）	138.9	[43]
CoPor-DBBP	>400	H₂O∶MeCN∶TEA= 4∶1∶2	286.7	[44]
AQ-TEA	>300	H₂O，16.7% TEOA（体积分数）	392	本工作

[1]	WANG Darui, SUN Hongmin, WANG Yiyan, TANG Zhimou, LI Rui, FAN Xueyan, YANG Weimin. Recent progress in zeolite for efficient catalytic reaction process [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 1-18.
[2]	LUO Fen, YANG Xiaoqi, DUAN Fanglin, LI Xiaojiang, WU Liang, XU Tongwen. Recent advances in the bipolar membrane and its applications [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 145-163.
[3]	GAI Hongwei, ZHANG Chenjun, QU Jingying, SUN Huailu, TUO Yongxiao, WANG Bin, JIN Xu, ZHANG Xi, FENG Xiang, CHEN De. Research progress on catalytic dehydrogenation process intensification for liquid organic hydride carrier hydrogen storage [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 164-185.
[4]	ZHANG Jiahao, LI Yingying, XU Yanlin, YIN Jiabin, ZHANG Jisong. Research advancement of continuous reductive amination in microreactors [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 186-197.
[5]	HENG Linyu, DENG Zhuoran, CHENG Daojian, WEI Bin, ZHAO Liqiang. Progress of high-throughput synthesis device for process reinforcement of metal catalyst preparation [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 246-259.
[6]	WANG Yiyan, WANG Darui, SHEN Zhenhao, HE Junlin, SUN Hongmin, YANG Weimin. Preparation and catalytic performance of fully crystalline MCM-22 zeolite catalyst [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 285-291.
[7]	ZHANG Mingyan, LIU Yan, ZHANG Xueting, LIU Yake, LI Congju, ZHANG Xiuling. Research progress of non-noble metal bifunctional catalysts in zinc-air batteries [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 276-286.
[8]	SHI Yongxing, LIN Gang, SUN Xiaohang, JIANG Weigeng, QIAO Dawei, YAN Binhang. Research progress on active sites in Cu-based catalysts for CO₂ hydrogenation to methanol [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 287-298.
[9]	XIE Luyao, CHEN Songzhe, WANG Laijun, ZHANG Ping. Platinum-based catalysts for SO₂ depolarized electrolysis [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 299-309.
[10]	YANG Xiazhen, PENG Yifan, LIU Huazhang, HUO Chao. Regulation of active phase of fused iron catalyst and its catalytic performance of Fischer-Tropsch synthesis [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 310-318.
[11]	ZHENG Qian, GUAN Xiushuai, JIN Shanbiao, ZHANG Changming, ZHANG Xiaochao. Photothermal catalysis synthesis of DMC from CO₂ and methanol over Ce_0.25Zr_0.75O₂ solid solution [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 319-327.
[12]	WANG Lele, YANG Wanrong, YAO Yan, LIU Tao, HE Chuan, LIU Xiao, SU Sheng, KONG Fanhai, ZHU Canghai, XIANG Jun. Influence of spent SCR catalyst blending on the characteristics and deNO _x performance for new SCR catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 489-497.
[13]	DENG Liping, SHI Haoyu, LIU Xiaolong, CHEN Yaoji, YAN Jingying. Non-noble metal modified vanadium titanium-based catalyst for NH₃-SCR denitrification simultaneous control VOCs [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 542-548.
[14]	SUN Yuyu, CAI Xinlei, TANG Jihai, HUANG Jingjing, HUANG Yiping, LIU Jie. Optimization and energy-saving of a reactive distillation process for the synthesis of methyl methacrylate [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 56-63.
[15]	YANG Hanyue, KONG Lingzhen, CHEN Jiaqing, SUN Huan, SONG Jiakai, WANG Sicheng, KONG Biao. Decarbonization performance of downflow tubular gas-liquid contactor of microbubble-type [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 197-204.

Enhanced photoelectric properties and photocatalytic CO₂ conversion by D-A conjugated polymerization

D-A共轭聚合强化光电性能及光催化CO₂转化

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 11

References 44

Related Articles 15

Recommended Articles

Metrics

Comments