Synthesis of a versatile pentacyclic building block for organic electronics. Issue 16 (14th June 2017)

• Record Type: Journal Article
• Authors: McDearmon, Brenden; Lim, Eunhee; O'Hara, Kathryn; Nakayama, Hidenori; Luo, Yingdong; Chabinyc, Michael L.; Hawker, Craig J.
• Is Part Of: Journal of polymer science. Volume 55:Issue 16(2017)
• Page Start: 2618
• Page End: 2628
• Publication Date: 2017-06-14
• Subjects: conjugated polymers -- copolymers -- organic electronics -- polycyclic building blocks -- redox polymers; 547
• DOI: 10.1002/pola.28656
• Languages: English
• ISSNs: 0887-624X

Abstract

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. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem.2017, 55, 2618–2628 Abstract : One‐step synthesis of a versatile pentacyclic quinone building block with redox active and electron‐accepting character is described. Reductive alkylation of this pentacyclic quinone yields an electron‐rich donor‐type unit with both systems subsequently incorporated into a diverse series of organic electronic materials.