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When the substituents of cyclopenta[hi]aceanthrylene change from trimethylsilyl to a cyano group, we observed reduced anti-aromaticity, decreased LUMO level from −2.49 to −3.59 eV, and inverted charge transport polarity from p type to n type, shedding light on the development of organic semiconductors based on cyclopenta-fused polycyclic aromatic hydrocarbons.

Graphical abstract: Substituent tailoring anti-aromaticity and charge transport polarity of cyclopenta[hi]aceanthrylenes

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