Research Progress on Organic Nanohoops/Nanogrids

doi:10.6023/A22110480

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (3): 289-308.DOI: 10.6023/A22110480 Previous Articles Next Articles

Review

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)

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

Cite this article

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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Fig. & Tab. 49

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Figure 25. Synthesis of CPP dimers bridged via pyrene derivatives

Figure 26. Synthesis of CPP dimers bridged via anthraquinone derivatives

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

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

Figure 29. Synthesis of directly linked CPP dimers

Figure 30. Synthesis of CPP dimers bridged via pentapterene

Figure 31. Synthesis of CPP dimers bridged via pentapterene derivatives

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

Figure 33. Synthesis of CPP dimers linked via bicarbazole bridges

Figure 34. Synthesis of CPP dimers connected via spirobifluorene bridges

Figure 35. Synthesis of CPP dimers connected via cyclotetrathiophene bridges

Figure 36. Five types of the nanogrids

Figure 37. Topological nanogrids structure

Figure 39. Synthesis of spirodigrid via Friedel-Crafts reaction

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

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

Figure 42. Synthesis of COP5 via alkyne metathesis

Figure 43. Synthesis of tetramer molecular cages via alkyne metathesis

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

Figure 45. Synthesis of tetrahedral molecular cages via alkyne metathesis

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

Figure 47. Synthesis of carbon nanocages

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

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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