Development of Organic Field-Effect Transistors Based on Chiral Perylene Diimides for Advanced Optoelectronics
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Helicenes can detect circularly polarized light (CPL) due to their strong chiroptical activity. But their complicity for synthesis and loosely solid-state packing limit their practical application. This study introduces a chiral induction strategy towards large-scale synthesis of helicene derivatives, tetrachlorinated diperylene diimides ((SSSS)-4CldiPDI or (RRRR)-4CldiPDI). By incorporating the chiral location group, (S/R)-1-cyclohexylethyl (Cy), the chirality directly transferred to the π-aromatic core and forms the PP- or MM-[4]helicene subunit. Notably, (SSSS)-Cy induces preferred PP helicity while (RRRR)-Cy leads to the MM helicity in monomers. The maximum photocurrent dissymmetry factor gph of +0.16 for (RRRR)-4CldiPDI and −0.15 for (SSSS)-4CldiPDI. This study shows a novel chiral induction strategy for designing helicene-based materials with both high dissymmetry factor and large charge carrier mobility.