Boronic esters: a simple route to discotic liquid crystals that are electron deficient

Abstract

The formation of boronic esters lowers the LUMO energy of hexamethoxytriphenylene by ∼1 V, converting the discotic core archetype from electron-rich to electron-deficient. Cyclic voltammetry gives E1/2 reduction values (ca. −1.2 V vs. Fc/Fc+) that are comparable to that of C60, the standard electron acceptor in organic electronics. Suitable peripheral functionalization imparts large mesophase temperature ranges. Homeotropic, columnar hexagonal phases with good charge carrier mobilities (up to 8 × 10−2 cm2 V−1 s−1) are observed.