亚酞菁的合成、性质与应用研究进展

doi:10.6023/cjoc202211020

摘要/Abstract

亚酞菁是酞菁缩环衍生物的典型代表, 表现出新颖的锥形结构、优异的发光性质和丰富的可调控性, 是一类有研究前景的新型荧光染料. 研究证明通过对亚酞菁轴向、外围或中心环结构的简单修饰, 可以有效调控其物理化学性质, 如溶解性、吸收/荧光发射、荧光量子产率、单线态氧产率等, 近年来引起了化学工作者的广泛关注. 介绍了亚酞菁的结构、性质和研究意义, 重点综述了亚酞菁的合成、结构和性质的关系及其在生物化学、材料化学和环境化学等领域的应用进展. 最后对亚酞菁的发展现状做了简要总结, 并对亚酞菁的发展进行了展望.

关键词: 亚酞菁, 结构, 光电性质, 应用

Subphthalocyanine, as a typical contracted analogue of phthalocyanine, exhibits novel cone structure, excellent luminescent properties and high flexibility of modification, which enables it as a new type of fluorescent dye with great research prospects. It has been proved that simple modifications of the axial, peripheral or central ring structure of subphthalocyanine can effectively regulate its physical and chemical properties, such as solubility, absorption/fluorescence emission, fluorescence quantum yield and singlet oxygen yield, and these properties have attracted extensive attentions from chemists in recent years. This review introduces the structures, properties and research significance of subphthalocyanine. Then, the progress in the synthesis, the relationship between properties and molecular structure of subphthalocyanin, and their applications in the area of biochemistry, material chemistry and environmental chemistry are reviewed emphatically. Finally, the development status of subphthalocyanine is summarized, and the further development of subphthalocyanine is discussed and proposed.

Key words: subphthalocyanine, structures, photoelectric properties, application

引用此文

周姝彤, 涂胜男, 高子健, 王叶梅, 孙莎莎. 亚酞菁的合成、性质与应用研究进展[J]. 有机化学, 2023, 43(8): 2628-2646.

Shutong Zhou, Shengnan Tu, Zijian Gao, Yemei Wang, Shasha Sun. Research Progress in Synthesis, Properties and Application of Subphthalocyanine[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2628-2646.

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图/表 34

图1. 酞菁、金属酞菁和亚酞菁的结构

Figure 1. Structures of phthalocyanine, metal-phthalocyanine and subphthalocyanine

图2. 共晶体1, 2和包合物3的结构[24-25]

Figure 2. Structures of co-crystal 1, 2 and inclusion compound 3 Reprinted with permission from Ref. [24]. Copyright ? 2018, American Chemical Society and from Ref. [25]. Copyright ? The Royal Society of Chemistry 2022.

图3. 酞菁与亚酞菁典型的紫外吸收谱图

Figure 3. Typical UV/vis absorption spectra of Pc and SubPc

图4. C3或C1对称的手性亚酞菁5~8结构

Figure 4. Structures of C3 or C1-symmetric SubPcs 5~8

图5. 亚酞菁9~11的结构

Figure 5. Structures of SubPc 9~11

图6. 亚酞菁12和13的结构

Figure 6. Structures of SubPc 12 and 13

图式1. 通过形成中间体SubPc-OTf 14合成轴向取代的亚酞菁

Scheme 1. Synthesis of axially substituted SubPcs via a triflate-SubPc 14 intermediate

图7. 亚酞菁15~18的结构

Figure 7. Structures of SubPc 15~18

图式2. 通过形成中间体SubPc(Cl)?AlCl3 19合成轴向取代的亚酞菁

Scheme 2. Synthesis of axially substituted SubPcs via a SubPc(Cl)?AlCl3 19 intermediate

图8. 亚酞菁20~24的结构

Figure 8. Structures of SubPc 20~24

图式3. 通过形成中间体SubPc(Cl)?Me3SiNu 25合成轴向取代的亚酞菁

Scheme 3. Synthesis of axially substituted SubPcs via a SubPc(Cl)?Me3SiNu 25 intermediate

图9. 亚酞菁26和27的结构

Figure 9. Structures of SubPc 26 and 27

图10. 亚酞菁28和29的结构

Figure 10. Structures of SubPc 28 and 29

图11. 亚酞菁30~32的结构

Figure 11. Structures of SubPc 30~32

图12. 亚酞菁33~36的结构

Figure 12. Structures of SubPc 33~36

图13. 亚酞菁38~40的结构

Figure 13. Structures of SubPc 38~40

图14. (a)亚酞菁41和42的结构; (b)亚酞菁41和42的模型及手性柱状聚合物[48]

Figure 14. (a) Structures of SubPc 41 and 42; (b) model of 41 and 42, and the corresponding homochiral columnar stacks Reprinted with permission from Ref. [48]. Copyright ? 2020, American Chemical Society.

图15. 亚酞菁43~46的结构

Figure 15. Structures of SubPc 43~46

图16. 亚酞菁47~51的结构

Figure 16. Structures of SubPc 47~51

图17. (a)铜酞菁或者(b)亚酞菁4作为供电子层的器件能级示意图[62]

Figure 17. Schematic energy level diagram for devices with (a) CuPc or (b) SubPc 4 as the donor layer Reprinted with permission from Ref. [62]. Copyright ? 2006, American Chemical Society.

Compound	X	λ_abs/nm	λ_em/nm
4	Cl	564	569
52	F	562	568
53	Br	566	572
54		561	570
55		564	571
56		567	575
57		569	577
58		566	581
59		562	571
60		563	592

表1. 亚酞菁4和52~60的结构及吸收/发射波长

Table 1. Structures of SubPcs 4 and 52~60, and their absorption/emission wavelength

图18. 亚酞菁30和61的结构

Figure 18. Structures of SubPc 30 and 61

图19. (a)亚酞菁4, 亚萘菁62和α-6T的结构; (b) α-6T/SubPc/SubNc体系结构示意图

Figure 19. (a) Structures of SubPc 4, SubNc 62 and α-6T; (b) Schematic representation of α-6T/SubPc/SubNc architecture

图20. 亚酞菁30和63~65的结构

Figure 20. Structures of SubPc 30 and 63~65

图21. 亚酞菁66和67的结构

Figure 21. Structures of SubPc 66 and 67

图22. 亚酞菁68、69和PBDBT-2F的结构

Figure 22. Structures of SubPc 68, 69 and PBDBT-2F

图23. 亚酞菁70~74的结构

Figure 23. Structures of SubPc 70~74

图24. 亚酞菁75~77的结构

Figure 24. Structures of SubPc 75~77

图25. 亚酞菁78~85的结构

Figure 25. Structures of SubPc 78~85

图26. 亚酞菁86的结构

Figure 26. Structures of SubPc 86

图27. (a)亚酞菁87~89的结构; (b)亚酞菁87~89及各种亚细胞荧光探针与HeLa细胞孵育4 h后的细胞内的荧光

Figure 27. (a) Structures of SubPc 87~89; (b)Visualization of the intracellular fluorescence of SubPc 87~89 (after incubation for 4 h) and various subcellular trackers in HeLa cells The corresponding bright-field and merged images are given in lines 1 and 5, respectively. The figures in line 2 show the fluorescence intensity profiles of 87~89 and the corresponding images of Hoechst 33342 and Lyso Tracker Green DND-26 in lines 3 and 4, respectively. Scale bar: 5 μm.

图28. 亚酞菁90的结构

Figure 28. Structures of SubPc 90

图29. (a)亚酞菁91的结构; (b)亚酞菁91溶液中加入四氟化丁胺(TBAF)后的吸收光谱变化; (c)亚酞菁91中加入不同阴离子后在696和565 nm处的吸收光谱的比值; (d)亚酞菁91溶液中加入不同阴离子后的归一化吸收光谱[80]

Figure 29. (a) Structures of SubPc 91; (b) The absorption spectral change of SubPc 91 upon addition of tetrabutylammonium fluoride (TBAF); (c) Absorption ratio of SubPc 91 between 696 nm and 565 nm to the anions; (d) Normalized absorption spectra of 91 in the presence of anions Reprinted with permission from Ref. [80]. Copyright ? 2007 The Chemical Society of Japan.

图30. 亚酞菁92的结构

Figure 30. Structures of SubPc 92

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