苝酰亚胺大环的研究进展

doi:10.6023/cjoc202410014

摘要/Abstract

设计和开发具有特定结构和特殊性质的新型大环一直是超分子化学和材料科学领域的前沿研究热点. 苝酰亚胺(PDI)作为一类重要的染料分子, 具有独特的光电特性和多样性的反应位点, 使其成为构筑大环的理想基元. 近年来, 通过PDI的酰亚胺位或苝核取代, 已经得到了许多结构多样的大环. 对PDI大环的研究进展进行了总结, 概述了它们的设计、合成以及结构特征, 并讨论了它们的性质和功能. 希望本文的讨论能够为研究者提供借鉴, 从而促进PDI化学、超分子化学和材料化学等领域的发展.

关键词: 苝酰亚胺, 大环, 合成, 超分子, 材料

The creation and development of new types of macrocycles with specifically tailored structures and unique properties are always one of the cutting-edge research in supramolecular chemistry and materials science. As one of the most important dye molecules, perylene diimide (PDI) possesses fascinating optical and elecetronic features, multiple reaction sites, making it an ideal building block for the construction of macrocycles. In recent years, a plethora of structurally diverse macrocycles have been obtained by carefully selecting the imide or core-substituents of the parent PDI. In this review, the advances in research into these PDI-based macrocycles are summarized. An overview of their design, synthesis as well as structural features is presented, while their properties and functions are also discussed. We aim for this review to serve as a valuable reference for researchers in the related fields and stimulate further advances in PDI chemistry, supramolecular chemistry and materials chemistry.

Key words: perylene diimide, macrocycle, synthesis, supramolecule, material

引用此文

何华西, 周和烨, 刘彬. 苝酰亚胺大环的研究进展[J]. 有机化学, 2025, 45(7): 2265-2282.

Huaxi He, Heye Zhou, Bin Liu. Advances in Perylene Diimide-Based Macrocycles[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2265-2282.

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图/表 26

图1. 苝酰亚胺的结构和衍生化位点图

Figure 1. Molecular structure and reactive sites of perylene diimide

图2. 通过“硫挤出”策略合成PDI大环1

Figure 2. Synthesis of PDI macrocycle 1 by sulfur extrusion

图3. PDI-C60大环2和3的化学结构

Figure 3. Chemical structures of PDI-C60 macrocycles 2 and 3

图4. 寡聚噻吩桥连的PDI大环4~8

Figure 4. Oligothiophene-bridged PDI macrocycles 4~8

图5. 三角形PDI大环9和10

Figure 5. Triangular PDI macrocycles 9 and 10

图6. 含吡啶盐基元的PDI大环11和12

Figure 6. Pyridinium-containing PDI macrocycles 11 and 12

图7. 手性的PDI大环13

Figure 7. Chiral PDI macrocycle 13

图8. 基于PDI大环的[2]索烃14和[3]索烃15

Figure 8. [2] catenane 14 and [3] catenane 15 constructed from PDI macrocycle

图9. 酰亚胺位衍生的二元PDI大环16~20

Figure 9. Bis-PDI macrocycles 16~20 connected via imide positions

图10. 刚性的二元PDI大环21和22

Figure 10. Structurally rigid PDI macrocycles 21 and 22

图11. 三角形的PDI大环23

Figure 11. Triangular PDI macrocycle 23

图12. 炔烃桥连的PDI大环24和25

Figure 12. Alkyne-bridged PDI macrocycles 24 and 25

图13. 对二甲苯桥连的二元PDI大环26

Figure 13. para-Xylylene bridged bis-PDI macrocycle 26

图14. 各种具有CH2-芳基-CH2连接基团的二元PDI大环27~31

Figure 14. Bis-PDI macrocycles 27~31 with various CH2-arylene-CH2 linkers

图15. PDI大环32及其溶剂调控的折叠行为

Figure 15. PDI macrocycle 32 and its solvent-templated folding behavior

图16. 具有固有手性PDI大环35和36的合成

Figure 16. Synthesis of inherently chiral PDI macrocycles 35 and 36

图17. 聚噻吩PDI大环37

Figure 17. Oligothiophene-PDI macrocycle 37

图18. PDI大环38和39

Figure 18. PDI macrocycles 38 and 39

图19. PDI共轭手性大环40

Figure 19. PDI-embedded chiral conjugated macrocycle 40

图20. 立体选择性合成手性PDI大环41

Figure 20. Stereoselective synthesis of chiral PDI macrocycle 41

图21. 共轭的二元PDI大环42

Figure 21. Conjugated bis-PDI macrocycle 42

图22. 二元PDI大环43

Figure 22. Bis-PDI macrocycle 43

图23. PDI手性碳卟啉大环44

Figure 23. PDI chiral carbaporphyrin macrocycle 44

图24. PDI分子弓45a~45d的化学结构

Figure 24. Chemical structures of PDI Bow 45a~45d

图25. 领结形的PDI双大环主体46

Figure 25. Bowtie-shape PDI bis(macrocyclic) host 46

图26. PDI衍生的单环和双环脱氢[20]轮烯47a~47d

Figure 26. PDI-integrated monocyclic and dicyclic dehydro[20]annulenes 47a~47d

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