Synthesis of a versatile pentacyclic building block for organic electronics

TitleSynthesis of a versatile pentacyclic building block for organic electronics
Publication TypeJournal Article
Year of Publication2017
AuthorsMcDearmon, Brenden, Eunhee Lim, Kathryn O'Hara, Hidenori Nakayama, Yingdong Luo, Michael L. Chabinyc, and Craig J. Hawker
JournalJournal of Polymer Science Part A: Polymer Chemistry
Volume55
Issue16
Start Page2618
Pagination2628
Abstract

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.