Synthesis of a versatile pentacyclic building block for organic electronics

McDearmon, B., Lim, E., O'Hara, K., Nakayama, H., Luo, Y., Chabinyc, M. L., Hawker, C. J.
J. Polym. Sci., Part A: Polym. Chem.
2017
55, 2618–2628

A new pentacyclic building block, benzodibenzofuranquinone (BDBFQ), is synthesized in a single step from the inexpensive and readily available feedstocks chloranil and 3-bromophenol. This versatile repeat unit is incorporated into a series of conjugated materials as either the redox active quinone form or as an electron-rich dialkylated benzodibenzofuran (BDBF) unit. To illustrate the performance that can be obtained from these systems, optical and electrochemical properties were studied via UV–vis–NIR spectroscopy and cyclic voltammetry. Thin-film morphology was characterized via grazing incidence wide-angle X-ray scattering with thin-film field-effect transistor measurements further demonstrating the utility of this system.