An electron-poor bowl-shaped naphthalimide-annulated corannulene with branched alkyl residues in the imide position was synthesized by a palladium-catalyzed cross-coupling annulation sequence. This dipolar compound exhibits strong absorption in the visible range along with a low-lying LUMO level at –3.85 eV, enabling n-type charge transport in organic thin-film transistors. Furthermore, we processed inverted bulk-heterojunction solar cells in combination with the two donor polymers PCE–10 and PM6 to achieve open-circuit voltages up to 1.04 V. By using a blend of the self-assembled naphthalimide-annulated corannulene and PCE–10, we were able to obtain a power conversion efficiency of up to 2.1%, which is to the best of our knowledge the highest reported value for a corannulene-based organic solar cell to date.

通过钯催化的交叉耦合环化序列，合成了在亚胺位置带有支链烷基残基的贫电子碗形萘酰亚胺环化的环戊二烯。这种偶极化合物在可见光范围内具有很强的吸收能力，在–3.85 eV处具有较低的LUMO能级，从而可以在有机薄膜晶体管中进行n型电荷传输。此外，我们结合两种供体聚合物PCE-10和PM6处理了反向体-异质结太阳能电池，以实现高达1.04 V的开路电压。通过使用自组装的萘二甲酰亚胺-环戊二烯和PCE-10的混合物，我们能够获得高达2.1％的功率转换效率，据我们所知，这是迄今为止基于Corannulene的有机太阳能电池的最高报道价值。