Introducing an orthogonally polarized electron-rich alkene: synthesis of a zwitterionic boron-containing π-conjugated system

The synthesis of an alkene is reported which is concurrently twisted (twist angle = 86.6(8)°), push-pull (dipole moment = 7.48 D), and electron-rich (E1/2 = -1.45 V and -0.52 V vs. Fc/Fc+) in nature, comprising a unique trinity combination for the alkene class of compounds. Subsequently, this newly synthesized alkene-motif was used as a donor for the synthesis of a zwitterionic boron-containing π-conjugated compound (dipole moment = 12.17 D) through an intramolecular charge transfer process exploiting the π-conjugated donor-acceptor system.