Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties

While heteroatom doping serves as a powerful strategy for devising novel polycyclic aromatic hydrocarbons (PAHs), the further fine-tuning of optoelectronic properties via the precisely altering of doping patterns remains a challenge. Herein, by changing the doping positions of heteroatoms in a diindenopyrene skeleton, we report two isomeric boron, sulfur-embedded PAHs, named Anti-B2S2 and Syn-B2S2, as electron transporting semiconductors. Detailed structure-property relationship studies revealed that the varied heteroatom positions not only change their physicochemical properties, but also largely affect their solid-state packing modes and Lewis base-triggered photophysical responses. With their low-lying frontier molecular orbital levels, n-type characteristics with electron mobilities up to 1.5 × 10−3 cm2 V−1 s−1 were achieved in solution-processed organic field-effect transistors. Our work revealed the critical role of controlling heteroatom doping patterns for designing advanced PAHs. Two isomeric boron, sulfur-embedded polycyclic aromatic hydrocarbons were prepared and showed distinct heteroatom doping pattern-depedent physicochemcial and optoelectronic properties. [Display omitted]