Recent Advances of Polycyclic Aromatic Compounds Containing Four-Membered Rings

doi:10.6023/cjoc202008036

Abstract

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

Cite this article

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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Fig. & Tab. 12

Scheme 1. Synthesis of compounds 4a and 4b

Scheme 2. Synthesis of compounds 13a and 13b

Scheme 3. Synthesis of compounds 17a~17c

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

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

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

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

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

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

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

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

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

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