无机手性纳米结构的可控构筑及其催化研究进展

doi:10.6023/A22070308

化学学报 ›› 2022, Vol. 80 ›› Issue (11): 1507-1523.DOI: 10.6023/A22070308 上一篇下一篇

综述

无机手性纳米结构的可控构筑及其催化研究进展

马进越^a^,^b, 黄露霏^a, 周宝文^c, 姚琳^a^,^*()

a 上海交通大学中英国际低碳学院上海 201306
b 中国矿业大学(北京) 化学与环境工程学院北京 100083
c 上海交通大学机械与动力工程学院上海 200240

投稿日期:2022-07-18 发布日期:2022-08-25
通讯作者: 姚琳

作者简介:

马进越, 1999年出生, 中国矿业大学(北京)化学与环境工程学院在读硕士研究生, 目前在上海交通大学中英国际低碳学院进行手性催化剂的光、电及热催化方面的研究.

黄露霏, 2000年出生, 硕士研究生. 2022年在中央民族大学生命与环境科学学院获得理学学士学位. 2022年起就读于上海交通大学中英国际低碳学院, 导师为姚琳副教授, 主要研究领域为手性催化剂的光、电及热催化.

周宝文, 上海交通大学副教授, 博士生导师, 国家海外高层次人才, 2016年在中国科学院化学研究所获博士学位. 2017年6月~2020年12月在加拿大McGill大学和美国密歇根大学电气工程与计算机科学系从事博士后研究. 研究兴趣为III-nitrides/Si人工光合作用集成器件与系统、清洁能源与动力和环境污染物控制.

姚琳, 上海交通大学副教授, 博士生导师. 2015年获得中国科学院理化技术研究所理学博士学位, 2018年~2020年在美国密歇根大学做访问学者和研究助理. 主要研究兴趣为光/热智能功能材料、无机手性材料的可控制备及其在低碳和能源领域的应用.

基金资助:
国家自然科学基金(51902318); 上海交通大学启动项目资助.

Construction and Catalysis Advances of Inorganic Chiral Nanostructures

Jinyue Ma^a^,^b, Lufei Huang^a, Baowen Zhou^c, Lin Yao^a()

a China-UK Low Carbon College, Shanghai Jiao Tong University, Shanghai 201306
b School of Chemical and Environmental Engineering, China University of Mining and Technology (Beijing), Beijing 100083
c School of Mechanical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2022-07-18 Published:2022-08-25
Contact: Lin Yao
Supported by:
National Natural Science Foundation of China(51902318); start-up project of Shanghai Jiaotong University.

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摘要/Abstract

具有强烈光学活性的无机手性结构因其具有独特的物理化学性质, 可将手性信号扩展至可见和近红外区域, 对于手性的检测与分析、手性合成、手性传感及相关光电领域的研究具有重要意义. 在过去的二十年里, 人们对无机手性结构进行了大量的研究, 从合成方法、手性起源理论到实际应用都取得了长足的进展. 重点聚焦具有手性催化应用潜力的无机手性纳米材料, 首先介绍了单个无机手性纳米粒子独特的手性效应、常用的构筑方法和手性起源机理, 并简要概述了无机纳米粒子作为构筑单元形成手性多级纳米结构的组装方法. 重点关注了无机手性纳米材料在手性催化领域的应用, 讨论了手性金属纳米结构、手性半导体纳米结构、手性陶瓷纳米结构及手性磁性纳米粒子用于手性催化的相关机理, 并对有代表性的最新进展进行了分析. 最后, 梳理了目前无机手性结构及其催化性能存在的不足和面临的挑战, 并对未来的研究方向进行了展望.

关键词: 手性起源, 纳米结构, 不对称催化, 光学活性, 表面等离子体共振

Inorganic chiral structures with outstanding optical activity can extend optical signals to visible and near infrared regions due to their unique physical and chemical properties, which are of great significance for the detection and analysis of chirality, chiral synthesis, chiral sensing and related photoelectronic research. In the past two decades, the studies have been extensively carried out on inorganic chiral structures, and great progress has been made from synthesis methods, origins of chirality and practical applications. This review focuses on inorganic chiral nanomaterials with potential applications in chiral catalysis. Firstly, the unique chiral effect, common construction methods and chiral origin mechanism of single inorganic chiral nanoparticles are introduced, and the assembly methods of chiral hierarchical nanostructures using inorganic nanoparticles as the building blocks are briefly summarized. The applications of inorganic chiral materials in the field of chiral catalysis are emphasized. The related mechanisms of chiral metal nanostructures, chiral semiconductor nanostructures, chiral nanoceramics and chiral magnetic nanoparticles in chiral catalysis are discussed, and the latest representative progress is analyzed. At the end, the shortcomings and challenges of the existed inorganic chiral structures and catalytic performance are reviewed, and the future research direction is prospected.

Key words: origin of chirality, nanostructure, asymmetric catalysis, optical activity, surface plasmon resonance

引用此文

马进越, 黄露霏, 周宝文, 姚琳. 无机手性纳米结构的可控构筑及其催化研究进展[J]. 化学学报, 2022, 80(11): 1507-1523.

Jinyue Ma, Lufei Huang, Baowen Zhou, Lin Yao. Construction and Catalysis Advances of Inorganic Chiral Nanostructures[J]. Acta Chimica Sinica, 2022, 80(11): 1507-1523.

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图/表 19

图1. 典型的手性分子及具有相似结构的无机手性材料 (a)具有四面体手性碳原子的氨基酸分子和金纳米粒子形成的手性四面体[12]; (b) DNA分子的双螺旋结构和金螺旋结构[14]; (c)胆甾相液晶结构及金纳米棒和纤维素纳米晶体形成的手性等离子体薄膜[13]

Figure 1. Typical chiral molecules and inorganic chiral materials with similar structures (a) An amino acid molecules with a tetrahedral chiral carbon atom and a chiral tetrahedron formed by Au nanoparticles[12]; (b) DNA double helix and gold helix[14]; (c) Cholesteric liquid crystal structure, chiral plasmonic films formed by gold nanorods and cellulose nanocrystals[13]

图2. Web of Science关于无机手性结构及其手性催化应用的相关研究检索结果

Figure 2. Retrieved result of inorganic chiral structures and their chiral catalytic applications in Web of Science

图3. 纳米粒子的手性来源示意图 (a) 无机核自身具有手性形状; (b)纳米粒子表面的不对称性[41]; (c)手性场效应[40]

Figure 3. Schematic diagram of chiral origin of nanoparticles (a) Inorganic core has chiral shape; (b) surface asymmetry of nanoparticles[41]; (c) chiral field effect[40]

图4. 合成手性金团簇的不同方法[54]

Figure 4. Different methods for synthesis of chiral gold clusters[54]

图5. (a)纳米粒子作为催化活性中心和(b)纳米粒子作为催化剂载体

Figure 5. (a) Nanoparticles as catalytic active parts and (b) nanoparticles as catalyst supports

图6. 辛可尼丁修饰的铂纳米粒子催化丙酮酸甲酯的不对称氢化反应

Figure 6. Asymmetric hydrogenation of methyl pyruvate catalyzed by cinchonidine-modified Pt nanoparticles

图7. 手性BINAP修饰的铂纳米粒子催化苯乙烯与三氯硅烷的不对称加氢硅烷化反应

Figure 7. Asymmetric hydrosilylation of styrene with trichlorosilane catalyzed by BINAP-modified Pt nanoparticles

图8. (a)手性印迹介孔铂的合成示意图及(b)苯乙醛酸还原为扁桃酸的对映选择性机理[88]

Figure 8. (a) Schematic illustration of the synthesis of chiral-imprinted mesoporous Pt and (b) illustration of the concept of enantioselectivity for the reduction of PGA to MA[88]

图9. (a)包封在手性自组装单分子膜/介孔二氧化硅载体中的金纳米团簇的制备示意图和形成单层膜的五种手性分子的化学结构、(b, c) Au@SAM/MCF-17催化的分子间环丙烷化和分子内环丙烷化反应[35]、(d) CeO2负载催化剂上苯乙酮的不对称加氢反应和(e, f) (R)-NOBIN在氧化铈负载的铱纳米团簇上的吸附、苯乙酮在多相手性催化剂上的吸附和对映选择性机理示意图[93]

Figure 9. (a) Preparation of Au nanoclusters encapsulated in chiral SAM/mesoporous MCF-17 support and chemical structures of five chiral molecules for SAM, (b, c) Au@SAM/MCF-17 catalyzed intermolecular cyclopropane synthesis and intramolecular cyclopropane synthesis[35], (d) hydrogenation of acetophenone over CeO2-supported catalysts, and (e, f) schematic diagram of adsorption of (R)-NOBIN on Ir10/CeO2, adsorption and enantioselectivity of acetophenone on heterogeneous chiral catalysts[93]

图10. l-脯氨酸修饰的ZnS量子点催化不对称羟醛缩合反应的反应机理[94]

Figure 10. Reaction mechanism of asymmetric Aldol condensation catalyzed by l-proline modified ZnS quantum dots[94]

图11. (a) CdSe量子点催化的4-乙烯苯甲酸类底物的同分子或异分子间[2＋2]环加成反应[99]、(b) SiO2@Au和SiO2@Au@TiO2纳米带的CD谱图以及(c) l-手性杂化催化剂与左旋/右旋圆偏振光之间的不对称相互作用原理图[101]

Figure 11. (a) Homo- and hetero-intermolecular [2＋2] photocycloadditions of 4-vinylbenzoic acid derivatives catalyzed by CdSe quantum dots[99], (b) CD spectra of the SiO2@Au and SiO2@Au@TiO2 nanoribbons and (c) asymmetric interaction between a left (l)-handed hybrid and LCP/RCP light[101]

图12. 圆偏振光照射下手性CdTe量子点选择性切割DNA的剪切模型(其中蓝色箭头表示断裂的键)[103]

Figure 12. DNA shearing model of Cys-CdTe quantum dots under circularly polarized light irradiation (the blue arrow indicates the cleaved bond)[103]

图13. 以手性介孔二氧化硅为多相固体催化剂对映选择性合成5-嘧啶基烷醇[114]

Figure 13. Enantioselective synthesis of 5-pyrimidinyl alkanol using chiral mesoporous silica as heterogeneous solid catalyst[114]

图14. (a) 苯丙氨酸修饰的氧化铈纳米粒子立体选择性催化氧化DOPA对映体的示意图和(b)苯丙氨酸与DOPA分子间的连接示意图[116]

Figure 14. (a) Illustration of stereoselective catalytic oxidation of the DOPA enantiomers by the phenylalanine-modified CeNP and (b) schematic diagram of the connection between phenylalanine and DOPA molecules[116]

图15. 手性胺-POMs催化剂的制备策略及手性二胺-H3PW12O40催化丙酮和对硝基苯甲醛的羟醛反应[126]

Figure 15. Preparation strategy of chiral amine-POMs catalyst and Aldol reaction of acetone with p-nitrobenzaldehyde catalyzed by chiral diamine-H3PW12O40[126]

图16. (a)手性离子液体-Mg3Al-POMs二维手性复合催化剂的合成示意图以及(b)二维手性复合催化剂催化不对称环氧化反应的机理示意图[127]

Figure 16. (a) Schematic illustration of the synthetic procedures of a series of chiral catalysts CILs-Mg3Al-POMs and (b) schematic illustration of the mechanism of enantioselective epoxidation[127]

图17. (a) 多形体-A、多形体-B和多形体-C的通道特性[131]、(b)用有机结构导向剂合成手性分子筛的示意图以及(c)环氧化物及分子筛螺旋孔的相对尺寸示意图[130]

Figure 17. (a) Channel characteristics of polymorph-A, polymorph-B, and polymorph-C[131], (b) schematic diagram of synthesis of chiral molecular sieve with organic structure-directing agent and (c) schematic diagram of relative size of epoxides and spiral holes of molecular sieves[130]

图18. (a)手性钌络合物修饰的磁铁矿纳米粒子及其催化的芳香酮不对称加氢反应[139]以及(b)手性BINAP配体修饰的FePd磁性纳米粒子作为不对称偶联反应的可回收催化剂[141]

Figure 18. (a) Chiral Ru complexes modified magnetite nanoparticles and its application in the asymmetric hydrogenation of aromatic ketones[139] and (b) FePd magnetic nanoparticles modified with chiral BINAP ligand as a recoverable catalyst for the asymmetric coupling reaction[141]

图19. (a) Fe3O4-l-脯氨酸纳米粒子的制备示意图和其催化的苯甲醛、苯胺和环己酮的一锅三组分不对称Mannich反应及(b) l-脯氨酸-Fe3O4手性催化剂催化Mannich反应的机理[142]

Figure 19. (a) Schematic procedure for the preparation of Fe3O4-l-proline nanoparticles and its catalytic one-pot, three-component Mannich reaction of benzaldehyde, aniline and cyclohexanone, and (b) proposed mechanism of Mannich reaction catalyzed by Fe3O4-l-proline[142]

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无机手性纳米结构的可控构筑及其催化研究进展

Construction and Catalysis Advances of Inorganic Chiral Nanostructures

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