含四元环的多环芳香化合物的研究进展

doi:10.6023/cjoc202008036

摘要/Abstract

含四元环的多环芳香化合物通常能够表现出独特的光物理和化学性质, 在很多领域具有潜在应用价值. 分别针对线型、角型、螺旋型和环型含四元环多环芳香化合物的合成方法、分子堆积方式、光电性质及载流子迁移率等方面进行归纳总结. 研究表明, 表面合成法更利于制得规则形貌的多环芳香化合物; 线型类分子表现出了较高的载流子迁移率; 角型分子通常显示出更高的反芳香性; 螺旋型分子具有好的旋光性及更大的光学带隙, 且该类材料中四元环的个数及其所在分子中的位置对材料的光电性质有着决定性的影响.

关键词: 多环芳香化合物, 有机共轭化合物, 四元环, 反芳香性

Polycyclic aromatic compounds containing four-membered rings usually exhibit unique photophysical and chemical properties, and have potential application value in many fields. The synthesis methods, intermolecular stacking behaviors, photoelectric properties and carrier mobilities of linear, angular, helical, and ring-shaped polycyclic aromatic compounds containing four-membered rings are reviewed. The research shows that the surface synthesis method is more conducive to the preparation of regular-shaped polycyclic aromatic compounds, linear molecules show higher carrier mobilities, angular molecules usually show higher anti-aromaticity, and helical molecules have optical rotation properties and a larger optical band gap. It should be emphasized that the numbers of four-membered rings and its position in molecules have a decisive influence on their photoelectric properties.

Key words: polycyclic aromatic compound, organic conjugated compound, four-membered ring, anti-aromaticity

引用此文

崔英翠, 夏德斌. 含四元环的多环芳香化合物的研究进展[J]. 有机化学, 2021, 41(3): 907-918.

Yingcui Cui, Debin Xia. Recent Advances of Polycyclic Aromatic Compounds Containing Four-Membered Rings[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 907-918.

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图/表 12

图式1. 化合物4a和4b的合成

Scheme 1. Synthesis of compounds 4a and 4b

图式2. 化合物13a和13b的合成

Scheme 2. Synthesis of compounds 13a and 13b

图式3. 化合物17a~17c的合成

Scheme 3. Synthesis of compounds 17a~17c

图1. 化合物17a~17c和18的紫外-可见光谱[20]

Figure 1. UV-Vis spectra of compounds 17a~17c and 18[20]

图2. 化合物17'和18'的核独立化学位移谱图[20]

Figure 2. NICS-XY scans of compounds 17' and 18'[20]

图3. 化合物31和32的紫外-可见光谱和发射光谱[31]

Figure 3. UV-Vis and emission spectra of compounds 31 and 32[31]

图4. 化合物35和36的化学结构式及它们的单晶结构[35]

Figure 4. Chemical structures of compounds 35, 36 and their single crystal structures[35]

图5. 化合物37的单晶结构及其合成化合物38的过程[39]

Figure 5. Single crystal structure of compound 37 and its synthesis process of compound 38[39]

图6. 化合物40的化学结构式及表面形成多孔网络的STM图像[45]

Figure 6. Chemical structure of compounds 30 and STM image of a porous network formed on the surface[45]

图7. 一个由化学结构叠加而成的[2+2]环结构的STM图像[46]

Figure 7. STM image of one formal [2+2] ring structure superimposed by the chemical structure[46]

图8. 化合物42~45的化学结构式[50-51]

Figure 8. Chemical structures of compounds 42~45[50-51]

图9. 化合物46的化学结构式及其单晶结构、晶体堆积[53]

Figure 9. Chemical structure of compounds 46 and its single crystal structure and crystal packing[53]

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