CdS纳米棒/含Ni多钨氧酸盐光催化苯硫酚氧化偶联耦合制氢

doi:10.1016/S1872-2067(24)60025-2

催化学报 ›› 2024, Vol. 61: 312-321.DOI: 10.1016/S1872-2067(24)60025-2

CdS纳米棒/含Ni多钨氧酸盐光催化苯硫酚氧化偶联耦合制氢

任梦真^a, 刘天府^a, 董媛媛^a^,^*(), 李正^a, 杨嘉新^a^,^b, 刁振恒^b, 吕红金^a^,^*(), 杨国昱^a

^a北京理工大学化学与化工学院, 原子分子簇科学教育部重点实验室, 光电转换材料北京市重点实验室, 北京 102488
^b长春工业大学化学工程学院, 吉林长春 130012

收稿日期:2024-02-15 接受日期:2024-03-26 出版日期:2024-06-18 发布日期:2024-06-20
通讯作者: * 电子信箱: dyy1111@bit.edu.cn (董媛媛),hlv@bit.edu.cn (吕红金).
基金资助:
国家自然科学基金(21871025);国家自然科学基金(21831001);国家自然科学基金(21706080);国家海外高层次人才引进计划青年项目;北理工高层次人才科研启动计划项目

Near-unity photocatalytic dehydrocoupling of thiophenols into disulfides and hydrogen using coupled CdS Nanorods and Ni-containing polyoxometalate

Mengzhen Ren^a, Tianfu Liu^a, Yuanyuan Dong^a^,^*(), Zheng Li^a, Jiaxin Yang^a^,^b, Zhenheng Diao^b, Hongjin Lv^a^,^*(), Guo-Yu Yang^a

^aMOE Key Laboratory of Cluster Science, Beijing Key Laboratory of Photoelectric/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 102488, China
^bSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, Jilin, China

Received:2024-02-15 Accepted:2024-03-26 Online:2024-06-18 Published:2024-06-20
Contact: * E-mail: E-mail: dyy1111@bit.edu.cn (Y. Dong), hlv@bit.edu.cn (H. Lv).
Supported by:
National Natural Science Foundation of China(21871025);National Natural Science Foundation of China(21831001);National Natural Science Foundation of China(21706080);Recruitment Program of Global Experts (Young Talents);BIT Excellent Young Scholars Research Fund

摘要/Abstract

摘要：

二硫化物是生物和药学有机分子合成的重要中间体, 并已广泛用于蛋白质功能化、药物传递系统和智能材料等领域. 然而, 在传统的合成策略中, 常使用昂贵或者有毒的有机氧化剂, 这不仅增加了合成成本并造成环境污染, 而且合成过程中容易出现选择性差、过度氧化等问题. 光催化硫醇/硫酚氧化偶联生成二硫化物是一种环境友好的生产路线, 但存在催化活性低以及光生载流子不完全利用等问题. 因此, 开发一种环境友好、成本低廉以及光生电子-空穴高效利用的光催化体系, 用于催化硫醇/硫酚氧化偶联并耦合制氢, 具有重要的基础研究意义和潜在应用价值.
本文构筑了一种Ni₄P₂/CdS耦合光催化体系, 该耦合体系由硫化镉纳米棒(CdS NRs)和含镍的多钨酸盐(Na₆K₄[Ni₄(H₂O)₂(PW₉O₃₄)₂]·32H₂O, 简称Ni₄P₂)组成. 在光催化氧化4-甲氧基苯硫酚(4-MTP)偶联生成二硫化物的同时, 能够释放出氢气, 并展现出较好的反应活性. 反应4 h后, 4-MTP的转化率高达98.39%, 二硫化物的选择性为95.0%, 二硫化物的收率达24.45 μmol, H₂的收率为25.96 μmol. 该耦合体系还展现出了良好的普适性, 以-NH₂, -C₂H₅, -CH₃, -Cl和-F作为取代基, 取代4-甲氧基苯硫酚中的甲氧基并作为底物进行反应, 生成相应二硫化物的选择性均超过97%. 透射电子显微镜(TEM)和高分辨率X射线光电子能谱(XPS)结果表明, CdS NRs在反应前后形貌保持不变, 稳定性较好. X射线光电子能谱表征发现, 反应后的CdS NRs表面没有检测到Ni元素的XPS信号峰, 说明Ni₄P₂催化剂附着在CdS NRs的表面, 并且能够在反应过程中保持分子的完整性. 红外光谱进一步证实了析氢催化剂Ni₄P₂催化剂的稳定性. 此外, 荧光光谱、寿命衰减以及光电流测试等系列实验结果表明, CdS NRs与Ni₄P₂之间存在协同作用, Ni₄P₂的存在明显地促进光生电子-空穴对的分离和迁移. 通过一系列对比实验, 证实了可见光在反应中的必要性, 以及电子和空穴在反应过程中的关键作用. 通过顺磁共振(EPR)检测到了•SC₆H₄(OCH₃)自由基中间体的存在, 证实了偶联产物是通过硫中心自由基生成的. EPR测试还显示, 加入Ni₄P₂催化剂后, 自由基中间体信号增强, 进一步验证了Ni₄P₂可以促进光生电子-空穴对的分离和迁移. 基于上述实验和表征结果, 我们提出了以下反应机理: 在可见光的照射下, 4-MTP被空穴氧化脱氢, 生成•SC₆H₄(OCH₃)自由基. 随后, 两个•SC₆H₄(OCH₃)自由基偶联生成二硫化物. 同时, Ni₄P₂捕获活性氢物种, 促进了氢气的析出, 最终实现了4-MTP氧化偶联生成二硫化物并耦合制氢的光催化循环.
综上所述, 本研究成功构筑了Ni₄P₂/CdS光催化反应体系, 实现了有机底物4-MTP的氧化增值与催化制氢的耦合反应. 该体系不仅显示出良好的催化活性, 还具备较好的稳定性和普适性, 为太阳能驱动下的化学转化提供了有效的途径, 并为太阳能的可持续利用提供了参考.

关键词: 脱氢偶联, 多金属氧酸盐, 硫化镉, 析氢, 光催化

Abstract:

Simultaneously harnessing the photogenerated electrons and holes to convert thiols into the value-added disulfides with the concomitant formation of H₂ represents a highly promising strategy for maximizing the conversion of solar energy into chemical energy. Herein, we report an effective catalytic system comprising CdS nanorods (NRs) and Ni-containing polyoxometalate (Na₆K₄[Ni₄(H₂O)₂(PW₉O₃₄)₂] (Ni₄P₂)) (Ni₄P₂/CdS), which exhibited efficient photocatalytic activities towards the near-unity dehydrocoupling of 4-methoxythiophenol (4-MTP) into disulfide and H₂ evolution. The photooxidative dehydrocoupling of 4-MTP can be finished after 4 h photocatalysis, leading to 98.39% conversion of 4-MTP with the yield of disulfide and H₂ reaching 24.45 and 25.96 μmol, respectively. The Ni₄P₂/CdS catalytic system also showed good photocatalytic recycling stability. Comprehensive experimental and characterization results indicated that the synergistic cooperation between CdS NRs and Ni₄P₂ facilitated the separation and migration of the photogenerated electron-hole pairs, thereby improving the photocatalytic dehydrocoupling of 4-MTP to disulfide coupling with hydrogen production.

Key words: Dehydrocoupling, Polyoxometalate, CdS, Hydrogen evolution, Photocatalysis

任梦真, 刘天府, 董媛媛, 李正, 杨嘉新, 刁振恒, 吕红金, 杨国昱. CdS纳米棒/含Ni多钨氧酸盐光催化苯硫酚氧化偶联耦合制氢[J]. 催化学报, 2024, 61: 312-321.

Mengzhen Ren, Tianfu Liu, Yuanyuan Dong, Zheng Li, Jiaxin Yang, Zhenheng Diao, Hongjin Lv, Guo-Yu Yang. Near-unity photocatalytic dehydrocoupling of thiophenols into disulfides and hydrogen using coupled CdS Nanorods and Ni-containing polyoxometalate[J]. Chinese Journal of Catalysis, 2024, 61: 312-321.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(24)60025-2

https://www.cjcatal.com/CN/Y2024/V61/I6/312

图/表 8

Fig. 1. (a) PXRD pattern of CdS NRs. The high-resolution Cd 3d (b) and S 2p (c) XPS spectra of CdS NRs. TEM (d) and HR-TEM (e) images of CdS NRs. (f) The lattice fringes of CdS NRs in the enlarged image of the red area in (e). The HAADF-STEM (g) and element mapping (h,i) images of CdS NRs.

Scheme 1. The equation of the dehydrocoupling of 4-MTP into 4-MPD and H2 evolution.

Fig. 2. The photocatalytic dehydrocoupling of 4-MTP as a function of usage amount of CdS NRs (a,b) and the H2O content (c,d). Standard conditions: 50 μmol 4-MTP, 10 mg CdS NRs, 6 mL CH3CN/H2O (1% vol. H2O), 10 μmol L-1 Ni4P2, under the illumination of blue LED light (450 nm) at 20 °C, 3 h, and using CH4 as an internal standard for GC quantification of H2 gas.

Fig. 3. (a) Comparison experiments using Ni4P2 and NiCl2 (40 μmol L?1, equivalent moles of Ni) as H2 evolution catalysts for 4 h photocatalysis. (b, c) The effects of the concentration of Ni4P2 on the photocatalytic activities. Standard conditions: 50 μmol 4-MTP, 10 mg CdS NRs, 6 mL CH3CN/H2O (1% vol. H2O), 10 μmol L?1 Ni4P2, under the illumination of blue LED light (450 nm) at 20 °C, 3 h, and using CH4 as an internal standard for GC quantification of H2gas. (d) The time profiles of the photooxidative dehydrocoupling of 4-MTP. (e) The photocatalytic recycling tests using fresh and isolated 10 mg CdS NRs + 10 μmol L?1 Ni4P2 catalyst. (f) FT-IR spectra of Ni4P2 before and after photocatalytic reaction.

Table 1 The photooxidative dehydrocoupling of other thiophenols using Ni4P2/CdS catalytic system a.

Entry	-R	Con.^b (%)	Sel.^c (%)	H₂ (μmol)	Disulfides (μmol)	e^-/h^{+ d}
1	-NH₂	62.75	99.64	16.59	16.81	0.99
2	-C₂H₅	62.89	97.60	15.76	15.73	1.00
3	-CH₃	77.23	98.99	19.25	19.31	1.00
4	-Cl	27.34	98.50	7.17	6.84	1.05
5	-F	32.26	98.94	7.77	7.98	0.97

Fig. 4. UV-vis spectrum (a) and the Mott-Schottky plots (b) of CdS NRs. The inset in (a) is the Tauc plots for CdS NRs. (c) The schematic potential diagram of the photooxidation of 4-MTP integrated with H2 evolution using Ni4P2/CdS catalytic system. The PL spectra (d), fittings of normalized photoluminescence decay kinetics (e), and the photocurrent tests (f) of CdS NRs, CdS NRs + Ni4P2, and CdS NRs + substrate.

Fig. 5. (a) The photocatalytic activities of control experiments. (b) The EPR signals of the reaction solution in the dark and light illustration after 5 min in the presence of CdS NRs and Ni4P2/CdS.

Scheme 2. The proposed photocatalytic mechanism of the present Ni4P2/CdS catalytic system towards the oxidative dehydrocoupling of 4-MTP and H2 evolution reaction.

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CdS纳米棒/含Ni多钨氧酸盐光催化苯硫酚氧化偶联耦合制氢

Near-unity photocatalytic dehydrocoupling of thiophenols into disulfides and hydrogen using coupled CdS Nanorods and Ni-containing polyoxometalate

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