Advances in Perylene Diimide-Based Macrocycles

doi:10.6023/cjoc202410014

Abstract

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

Cite this article

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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Fig. & Tab. 26

Figure 1. Molecular structure and reactive sites of perylene diimide

Figure 2. Synthesis of PDI macrocycle 1 by sulfur extrusion

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

Figure 4. Oligothiophene-bridged PDI macrocycles 4~8

Figure 5. Triangular PDI macrocycles 9 and 10

Figure 6. Pyridinium-containing PDI macrocycles 11 and 12

Figure 7. Chiral PDI macrocycle 13

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

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

Figure 10. Structurally rigid PDI macrocycles 21 and 22

Figure 11. Triangular PDI macrocycle 23

Figure 12. Alkyne-bridged PDI macrocycles 24 and 25

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

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

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

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

Figure 17. Oligothiophene-PDI macrocycle 37

Figure 18. PDI macrocycles 38 and 39

Figure 19. PDI-embedded chiral conjugated macrocycle 40

Figure 20. Stereoselective synthesis of chiral PDI macrocycle 41

Figure 21. Conjugated bis-PDI macrocycle 42

Figure 22. Bis-PDI macrocycle 43

Figure 23. PDI chiral carbaporphyrin macrocycle 44

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

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

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

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