Liquid–crystalline perylene tetracarboxylic acid bisimide bearing oligosiloxane chains with high electron mobility and solubility

Liquid–crystalline perylene tetracarboxylic acid bisimide derivatives 1 and 2 bearing 1,1,1,2,2,3,3-heptamethyltrisiloxane chains at the end of alkyl side-chains have been synthesized. Compound 1 having four trisiloxane chains exhibits a hexagonal columnar phase at room temperature. Time-of-flight measurement reveals that the electron mobility in the columnar phase of compound 1 exceeds 10−3 cm2 V−1 s−1 at room temperature. In contrast, compound 2 bearing two trisiloxane chains is not mesomorphic. These two compounds are soluble in various organic solvents except for alcohols and thin films can be produced by a spin-coating method.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► New n-type perylene tetracarboxylic acid bisimide (PTCBI) derivatives were synthesized. ► The semiconductors have trisiloxane moieties at the end of their alkyl side chains. ► A PTCBI compound bearing four trisiloxane chains exhibits a columnar phase at room temperature. ► The electron mobility in the columnar phase is on the order of 10−3 cm2 V−1 s−1. ► These compounds are solution-processable and thin films can be produced by a spin-coating method.