有机纳米环/格的研究进展

doi:10.6023/A22110480

化学学报 ›› 2023, Vol. 81 ›› Issue (3): 289-308.DOI: 10.6023/A22110480 上一篇下一篇

综述

有机纳米环/格的研究进展

魏颖, 周平, 陈鑫, 包秋景, 解令海^*()

南京邮电大学分子系统与有机器件研究中心(CMSOD) 信息材料与纳米技术研究院有机电子与信息显示国家重点实验室南京 210023

投稿日期:2022-11-30 发布日期:2023-01-03

作者简介:

魏颖, 南京邮电大学材料科学与工程学院副研究员、硕士生导师. 2005至2009年就读于吉林化工学院, 获得学士学位. 2009至2014年就读于东北师范大学化学学院, 获得博士学位. 主要研究方向为有机方法学以及有机/聚合物光电材料的合成及其性能.

解令海, 南京邮电大学信息材料与纳米技术研究院/材料科学与工程学院教授、博士生导师, 国家百千万人才工程人选, 享受国务院政府特殊津贴. 2000年和2003年分别获得东北师范大学学士学位和汕头大学硕士学位. 2003至2006年就读于复旦大学先进材料研究院, 获得博士学位. 长期从事有机智能与第四代半导体研究, 涉及柔性电子、人工化学智能与智能化学、智能机器人化学家等未来领域的基础研究.

基金资助:
国家自然科学基金(22071112); 国家自然科学基金(22275098); 江苏省高校自然科学研究面上项目(20KJB150038); 有机电子与信息显示国家重点实验室资助项目(GDX2022010005); 有机电子与信息显示国家重点实验室资助项目(GZR2022010011)

Research Progress on Organic Nanohoops/Nanogrids

Ying Wei, Ping Zhou, Xin Chen, Qiujing Bao, Linghai Xie()

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, Nanjing 210023, China

Received:2022-11-30 Published:2023-01-03
Contact: *E-mail: iamlhxie@njupt.edu.cn
Supported by:
National Natural Science Foundation of China(22071112); National Natural Science Foundation of China(22275098); Natural Science Research Project of Universities in Jiangsu Province(20KJB150038); Project of State Key Laboratory of Organic Electronics and Information Displays, Nanjing University of Posts and Telecommunications(GDX2022010005); Project of State Key Laboratory of Organic Electronics and Information Displays, Nanjing University of Posts and Telecommunications(GZR2022010011)

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摘要/Abstract

径向共轭的碳纳米环作为碳纳米管的纳米片段, 在合成化学、立体化学、超分子化学和材料科学领域引起了极大的关注. 从几何结构角度来看, 纳米环的结构分为单环纳米环和多环纳米环. 其中, 单环纳米环的构建模块主要有苯或多环芳烃以及大环, 与以苯或多环芳烃为模块构造的单环纳米环相比, 以大环为构建模块的单环纳米环和多环纳米环不仅具有特殊的拓扑结构还具有较高的荧光量子产率、较大的空腔等特点. 目前这类具有拓扑结构的纳米环分子在主客体掺杂、储能材料、多孔和有机光电材料等领域体现出重要的研究价值. 因此本综述将重点对卟啉类单环纳米环、“8”字型纳米环、纳米格以及更复杂的碳纳米笼的合成方法进行全面的综述.

关键词: 纳米环, 多环, 合成方法, 大环, 纳米格

Radial conjugated carbon nanohoops, as nanofragments of carbon nanotubes, have attracted great attention in the fields of synthetic chemistry, stereochemistry, supramolecular chemistry and materials science. The structure of nanohoops can be divided into monocyclic and multicyclic nanohoops according to the geometric angle. The main building blocks of monocyclic nanohoops are benzene, polycyclic aromatic hydrocarbons and macrocycles, the monocyclic nanohoops with macrocycle as the building blocks and multicyclic nanohoops not only have special topological structure but also have the characteristics of high fluorescence quantum yield and large cavity. At present, such nanohoops with topological structure have important research value in the fields of host-guest doping, energy storage materials, porous and organic optoelectronic materials. Therefore, this review will focus on the synthetic methods of porphyrin monocyclic nanohoops with macrocycle as building blocks, figure-of-eight nanohoops and nanogrids, and more complex carbon nanocages.

Key words: nanohoop, multicyclic, synthetic method, macrocycle, nanogrid

引用此文

魏颖, 周平, 陈鑫, 包秋景, 解令海. 有机纳米环/格的研究进展[J]. 化学学报, 2023, 81(3): 289-308.

Ying Wei, Ping Zhou, Xin Chen, Qiujing Bao, Linghai Xie. Research Progress on Organic Nanohoops/Nanogrids[J]. Acta Chimica Sinica, 2023, 81(3): 289-308.

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图/表 49

图1. 卟啉单体通过Glaser偶联制备卟啉多聚体

Figure 1. Synthesis of porphyrin multimers via Glaser coupling from porphyrin monomers

图2. 通过Suzuki-Miyaura偶联反应制备了meso-meso连接的环状卟啉八聚体

Figure 2. Meso-meso-linked cyclic porphyrin octamer was synthesized via Suzuki-Miyaura coupling reaction

图3. 在两个卟啉的meso位用二联噻吩桥连的环状卟啉的合成

Figure 3. Synthesis of cyclic porphyrin connected by thiophene bridges at the meso position of two porphyrins

图4. 在两个卟啉的β位用噻吩桥连的环状卟啉的合成

Figure 4. Synthesis of cyclic porphyrin connected by thiophene bridges at the β position of two porphyrins

图5. meso-β位直接连接的环状卟啉合成

Figure 5. meso-β directly linked cyclic porphyrin was synthesized

图6. 通过Sonogashira偶联反应制备环状卟啉三聚体

Figure 6. Cyclic porphyrin trimers was synthesized via Sonogashira coupling reaction

图7. 通过Sonogashira偶联反应制备乙炔基连接的锌/钴卟啉

Figure 7. Ethynyl-linked Zn/Co porphyrin was synthesized via Sonogashira coupling reaction

图8. 通过Yamamoto偶联反应制备环状卟啉拓扑大环

Figure 8. Cyclic porphyrin topological macrocycles were synthesized via Yamamoto coupling reaction

图9. 以联吡啶和三嗪为模板制备环状卟啉拓扑结构

Figure 9. Bipyridine and triazine were used as templates to synthesize cyclic porphyrin topologies

图10. 线性卟啉二聚体以T6为模板制备环状卟啉六聚体

Figure 10. Cyclic porphyrin hexamer was synthesized from linear porphyrin dimer under T6 template

图11. 卟啉单体在T6模板下制备环状卟啉六聚体

Figure 11. Cyclic porphyrin hexamer was synthesized from porphyrin monomer under T6 template

图12. 线性卟啉三聚体在T6模板下制备环状卟啉六聚体c-P6Cu2

Figure 12. Cyclic porphyrin hexamer c-P6Cu2 was synthesized from linear porphyrin trimer under T6 template

图13. 线性卟啉六聚体在T6模板下制备环状卟啉六聚体

Figure 13. Cyclic porphyrin hexamer was synthesized from linear porphyrin hexamer under T6 template

图14. 线性的卟啉六聚体分别在T6和T6*模板制备环状卟啉六聚体

Figure 14. Cyclic porphyrin hexamers were synthesized from linear porphyrin hexamer under T6 and T6* templates, respectively

图15. 卟啉单体在T4, T6模板下制备环状卟啉拓扑结构

Figure 15. Cyclic porphyrin topologies were synthesized from porphyrin monomer under T4 and T6 templates, respectively

图16. 卟啉单体在环糊精模板下制备环状卟啉拓扑结构

Figure 16. Cyclic porphyrin topologies were synthesized from porphyrin monomer under cyclodextrin templates

图17. 卟啉单体以二茂铁基和心环烯模板制备环状卟啉拓扑结构

Figure 17. Cyclic porphyrin topologies were synthesized from porphyrin monomer using ferrocene-based and cardiocycline templates

图18. 游标模板法合成12-卟啉纳米环

Figure 18. Synthesis of a 12-porphyrin nano-ring by vernier templating

图19. 经典模板法合成12-卟啉纳米环

Figure 19. Synthesis of a 12-porphyrin nano-ring by classic template

图20. 分别以T6和T8为模板制备卟啉纳米24-卟啉纳米环

Figure 20. Synthesis of a 24-porphyrin nano-ring under T4, T6 templates, respectively

图21. 分别以T4和T5为模板制备环状卟啉拓扑结构

Figure 21. Cyclic porphyrin topologies were synthesized under T4 and T5 templates, respectively

图22. 分别以T6和T8为模板制备不同尺寸的环状卟啉结构

Figure 22. Cyclic porphyrin structures of different sizes were synthesized using T6 and T8 as templates, respectively

图23. 各种基团连接的“8”字型纳米环

Figure 23. Figure-of-eight nanohoop connected by various groups

图24. 苯和萘桥连的CPP二聚体的合成

Figure 24. Synthesis of CPP dimers linked via benzene and naphthalene

图25. 芘衍生物桥连的CPP二聚体的合成

Figure 25. Synthesis of CPP dimers bridged via pyrene derivatives

图26. 蒽醌衍生物桥连的CPP二聚体的合成

Figure 26. Synthesis of CPP dimers bridged via anthraquinone derivatives

图27. 芘衍生物不同位置桥连的CPP二聚体的合成

Figure 27. Synthesis of CPP dimers bridging pyrene derivatives at different locations

图28. C—C单键连接的CPP二聚体的合成

Figure 28. Synthesis of CPP dimers bridged via C—C single-bond

图29. 直接连接的CPP二聚体的合成

Figure 29. Synthesis of directly linked CPP dimers

图30. 五蝶烯桥连的CPP二聚体的合成

Figure 30. Synthesis of CPP dimers bridged via pentapterene

图31. 五蝶烯衍生物桥连的CPP二聚体的合成

Figure 31. Synthesis of CPP dimers bridged via pentapterene derivatives

图32. 三蝶烯连接三个CPP类拓扑结构的合成

Figure 32. Synthesis of triptene-linked three CPP class topologies

图33. 联咔唑桥连的CPP二聚体的合成

Figure 33. Synthesis of CPP dimers linked via bicarbazole bridges

图34. 螺二芴桥连的CPP二聚体的合成

Figure 34. Synthesis of CPP dimers connected via spirobifluorene bridges

图35. 环八四噻吩桥连的CPP二聚体的合成

Figure 35. Synthesis of CPP dimers connected via cyclotetrathiophene bridges

图36. 五种类型的单元纳米格

Figure 36. Five types of the nanogrids

图37. 拓扑纳米格结构

Figure 37. Topological nanogrids structure

Figure 38. 通过傅克反应制备“日”字格 Synthesis of “日”nanogrids via Friedel-Crafts reaction

图39. 通过傅克反应制备螺二格

Figure 39. Synthesis of spirodigrid via Friedel-Crafts reaction

图40. 通过Eglington-Gaser偶联制备苯基二乙炔单元连接的分子笼

Figure 40. Molecular cages linked via Eglington-Gaser coupling into phenyldiacetylene units

图41. 低浓度下通过Eglington-Gaser偶联制备苯基二乙炔单元连接的分子笼

Figure 41. At low concentrations, molecular cages linked via Eglington-Gaser coupling into phenyldiacetylene units

图42. 炔烃复分解合成COP5

Figure 42. Synthesis of COP5 via alkyne metathesis

图43. 炔烃复分解制备四聚体分子笼

Figure 43. Synthesis of tetramer molecular cages via alkyne metathesis

图44. 炔烃复分解制备含咔唑分子笼

Figure 44. Synthesis of carbazole-containing molecular cages via alkyne metathesis

图45. 炔烃复分解制备四面体笼

Figure 45. Synthesis of tetrahedral molecular cages via alkyne metathesis

图46. 组装/还原消除策略制备3D笼

Figure 46. Synthesis of 3D cages via assembly/reduction elimination strategy

图47. 碳纳米笼的合成

Figure 47. Synthesis of carbon nanocages

图48. 通过傅克反应一步制备3D纳米格拓扑结构

Figure 48. One-step synthesis of 3D nanogrids topology via Friedel- Crafts reaction

图49. 通过傅克反应制备[4]笼和[2]笼

Figure 49. Synthesis of [4] cages and [2] cages via Friedel- Crafts reaction

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有机纳米环/格的研究进展

Research Progress on Organic Nanohoops/Nanogrids

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