利用金属-自由基相互作用调控自由基的定向转化

doi:10.1016/S1872-2067(22)64181-0

催化学报 ›› 2023, Vol. 45: 120-131.DOI: 10.1016/S1872-2067(22)64181-0

利用金属-自由基相互作用调控自由基的定向转化

黄志鹏^a^,^b^,¹, 杨阳^c^,¹, 穆骏驹^a, 李根恒^a^,^d, 韩建宇^a^,^b, 任濮宁^a^,^b, 张健^a, 罗能超^a, 韩克利^c, 王峰^a^,^*()

^a中国科学院大连化学物理研究所, 催化国家重点实验室, 辽宁大连116023
^b中国科学院大学, 北京100049
^c中国科学院大连化学物理研究所, 分子反应动力学国家重点实验室, 辽宁大连116023
^d大连理工大学张大煜化学学院, 辽宁大连116024

收稿日期:2022-09-22 接受日期:2022-10-09 出版日期:2023-02-18 发布日期:2023-01-10
通讯作者: 王峰
作者简介:第一联系人：
¹共同第一作者
基金资助:
国家重点研发计划-中国和意大利政府间合作项目(2018YFE0118100);国家自然科学基金(22025206);国家自然科学基金(21721004);国家自然科学基金(21991090);国家自然科学基金(22002159);国家自然科学基金(22088102);国家自然科学基金(21833009);辽宁省“兴辽英才计划”项目(XLYC2002012);辽宁省“兴辽英才计划”项目(XLYC1802126);中国科学院洁净能源创新研究院-榆林学院联合基金(YLU-DNL Fund 2021019);中国科学院科研仪器设备研制项目(YJKYYQ20190003);大连市科技创新基金(2019J12GX031);大连化物所创新研究基金(DICP I202009)

Controlling the reactions of free radicals with metal-radical interaction

Zhipeng Huang^a^,^b^,¹, Yang Yang^c^,¹, Junju Mu^a, Genheng Li^a^,^d, Jianyu Han^a^,^b, Puning Ren^a^,^b, Jian Zhang^a, Nengchao Luo^a, Ke-Li Han^c, Feng Wang^a^,^*()

^aState Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences,Dalian 116023, Liaoning, China
^bUniversity of Chinese Academy of Sciences, Beijing 100049, China
^cState Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^dZhang Dayu School of Chemistry, Dalian University of Technology, Dalian 116024, Liaoning, China

Received:2022-09-22 Accepted:2022-10-09 Online:2023-02-18 Published:2023-01-10
Contact: Feng Wang
About author:First author contact:
¹Contributed equally to this work.
Supported by:
Ministry of Science and Technology of the People's Republic of China(2018YFE0118100);National Natural Science Foundation of China(22025206);National Natural Science Foundation of China(21721004);National Natural Science Foundation of China(21991090);National Natural Science Foundation of China(22002159);National Natural Science Foundation of China(22088102);National Natural Science Foundation of China(21833009);Liaoning Revitalization Talents Program(XLYC2002012);Liaoning Revitalization Talents Program(XLYC1802126);Joint Fund of the Yulin University and the Dalian National Laboratory for Clean Energy(YLU-DNL Fund 2021019);Scientific Instrument Developing Project of the Chinese Academy of Sciences(YJKYYQ20190003);Dalian Science and Technology Innovation Fund(2019J12GX031);Dalian Institute of Chemical Physics, Chinese Academy of Sciences(DICP I202009)

摘要/Abstract

摘要：

近年来光催化研究的兴起极大地促进了传统自由基化学的发展. 在光照下, 被激发的光催化剂会与底物发生电荷转化, 从而在非常温和的条件下产生自由基中间体. 自由基物种非常活泼, 可快速地发生各类C-C偶联或者断键反应, 但自由基的高活性同时意味着难以实现其可控的转化. 特别是在多相光催化体系中, 实现自由基物种的定向转化仍非常困难. 光照条件下, 半导体光催化剂的光生电子或空穴可以活化底物产生各种活泼的自由基物种, 但往往在随后的自由基转化反应中扮演着旁观者的角色. 即产生的自由基中间体可以自由地扩散和反应, 它们会彼此碰撞发生自由基-自由基偶联反应, 与表面活性氢物种反应, 或者进一步被氧化为相应的碳正离子进而转化为一系列复杂的产物. 因此, 多相光催化剂表面不受控的自由基反应限制了其在很多重要领域(例如合成化学以及生物质转化等)的进一步应用.
本文提出在半导体催化剂表面构建特定的金属位点, 利用金属-自由基相互作用来调控在半导体表面产生的自由基物种的定向转化. 以苯乙酸在金属/TiO₂催化剂上的光催化脱羧为模型反应进行研究.光照条件下, 苯乙酸在TiO₂上被光生空穴氧化发生脱羧反应, 产生苄基自由基. 若该自由基物种能被稳定在负载的金属颗粒表面, 就会优先与金属上光生电子还原质子产生的活性氢物种反应, 选择性地生成甲苯, 否则将会自由地碰撞反应, 得到联苄和甲苯的混合物. 结果表明, Pd/TiO₂能高选择性地催化苯乙酸脱羧产生甲苯, 得到与其它金属/TiO₂催化剂截然不同的产物分布. 同时, 利用瞬态吸收光谱可原位地观测产生的苄基自由基在金属/TiO₂催化剂上转化. 研究发现, 苄基自由基的Pd/TiO₂催化剂上的转化遵循准一级的反应动力学行为, 而非完全自由的自由基转化路径. 基于以上结果, 推测Pd纳米颗粒能够将在TiO₂上产生的自由基稳定在其表面, 并调控自由基的后续转化. DFT计算表明, Pd与自由基物种存在强电子相互作用, 使其对自由基具有很强的亲和力. 这种强金属-自由基相互作用为高效自由基转化体系的设计提供了可能. 在催化剂表面构建特定的金属位点, 例如Pd纳米颗粒, 可将在半导体光催化剂上产生的自由基物种稳定在表面, 避免其发生无序的自由基反应, 同时进一步修饰金属位点, 即可促进表面稳定的自由基物种的定向转化.

关键词: 金属-自由基相互作用, 自由基反应, 光催化, 反应机理, 金属催化剂

Abstract:

Radicals are key intermediates in numerous reactions. Their high reactivity enables various transformations to occur under mild conditions, however, also brings great challenges to control their reactions especially over heterogeneous catalysts. Here we propose to use metal nanoparticles to directly steer the conversion of free radical species. Results from photocatalytic reactions, in situ transient absorption spectroscopy, and theoretical simulation demonstrate that supported Pd nanoparticles can efficiently stabilize free radical species generated from photo-excited TiO₂, and thus manipulate their conversion on catalyst surface, owing to the enhanced electronic interactions between metal and radical species. These understandings are crucial for the design of advanced heterogeneous catalytic systems with controllable radical reactions.

Key words: Metal-radical interaction, Radical reaction, Photocatalysis, Catalytic mechanism, Metal catalysis

黄志鹏, 杨阳, 穆骏驹, 李根恒, 韩建宇, 任濮宁, 张健, 罗能超, 韩克利, 王峰. 利用金属-自由基相互作用调控自由基的定向转化[J]. 催化学报, 2023, 45: 120-131.

Zhipeng Huang, Yang Yang, Junju Mu, Genheng Li, Jianyu Han, Puning Ren, Jian Zhang, Nengchao Luo, Ke-Li Han, Feng Wang. Controlling the reactions of free radicals with metal-radical interaction[J]. Chinese Journal of Catalysis, 2023, 45: 120-131.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(22)64181-0

https://www.cjcatal.com/CN/Y2023/V45/I2/120

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Fig. 1. (a) Reaction network of phenylacetic acid conversion over metal/TiO2 catalyst. (b) Photocatalytic conversion of phenylacetic acid and 2-phenylisobutyric acid over metal/TiO2 catalysts. Reaction conditions: substrate (0.15 mmol), photocatalyst (5 mg), acetonitrile (1.2 mL), Ar (0.1 MPa), room temperature (30 ± 5 ?°C), LEDs (365 nm, 18 W) irradiation for 3 h. Conversion and selectivity were determined by GC analysis.

Fig. 2. TA spectra averaged over 0.25-0.35 μs in the presence (blue) and absence (orange) of phenylacetic acid over Pt/TiO2 (a), Au/TiO2 (b), Rh/TiO2 (c), Ni/TiO2 (d), and Pd/TiO2 (e) catalysts. Transient decay of benzyl radical absorption signal at selected wavelength over Pt/TiO2 (f), Au/TiO2 (g), Rh/TiO2 (h), Ni/TiO2 (i), and Pd/TiO2 (j) catalysts. △Abs, the change in absorbance after laser pulse excitation; a, the kinetic weight coefficient; R2, the coefficient of fitting determination. Curves drawn on top of the data are guides to the eye.

Fig. 3. (a) The calculated binding energy of benzyl radical on different metal surfaces. The calculated partial density of states for benzyl radical binding on Pd (111) (b) and Pt (111) (c).

Scheme 1. Hydrodecarboxylation of carboxylic acids over Pd/TiO2. Yields were determined by GC analysis. a Isolated yield. b NMR yield. c HPLC yield. d Reaction was carried out on a 3.75 mmol (0.863 g) scale, reaction time (18 h).

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利用金属-自由基相互作用调控自由基的定向转化

Controlling the reactions of free radicals with metal-radical interaction

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