Perylene-based semiconductors and methods of preparation and use thereof

摘要

Provided are semiconductors prepared from an enantiomerically enriched mixture of a nitrogen-functionalized rylene bis(dicarboximide) compound. Specifically, the enantiomerically enriched mixture has unexpected electron-transport efficiency compared to the racemate or either of the enantiomers in optically pure form.

主权项

1. A thin film semiconductor comprising an enantiomerically enriched mixture of a compound of formula I: wherein: R1 and R2 are identical or substantially identical and are selected from the group consisting of a branched C4-40 alkyl group, a branched C4-40 alkenyl group, and a branched C4-40 haloalkyl group; wherein the branched C4-40 alkyl group, the branched C4-40 alkenyl group, and the branched C4-40 haloalkyl group have a formula selected from the group consisting of: wherein R′ is a C1-20 alkyl group or a C1-20 haloalkyl group; R″ is different from R′ and is selected from the group consisting of a C1-20 alkyl group, a C2-20 alkenyl group, and a C1-20 haloalkyl group; and an asterisk (*) denotes a stereogenic center such that R1 and R2 have either an R- or S-configuration; and wherein a ratio of (R,R)-stereoisomers:(S,S)-stereoisomers or a ratio of (S,S)-stereoisomers:(R,R)-stereoisomers of the compound of formula I in the enantiomerically enriched mixture is between about 0.8:0.2 and about 0.98:0.02.