Polyaromatic molecules for OLEC applications

Abstract

The synthesis of several novel extended aromatic and heteroaromatic molecules is reported, for potential applications in organic electronics such as Organic Light-Emitting Diodes (OLEDs) and Organic Light-Emitting Electrochemical Cells (OLECs). Initially, naphthalene containing polyaromatics were synthesized following a synthetic route previously developed in our group. A three-step synthetic strategy was followed to obtain a key naphthalene containing intermediate, which was then coupled with various aromatic and heteroaromatic components via a Suzuki-coupling reaction in a bidirectional synthetic sequence, followed by a bidirectional base-catalyzed cyclization reaction to afford the final polyaromatics. A similar approach was followed for the synthesis of carbazole containing polyaromatics. A four-step synthetic strategy previously developed in our group was followed to obtain a key carbazole containing intermediate which was then coupled in a bidirectional manner with various aromatic and heteroaromatic components via a Suzuki-coupling reaction. A bidirectional base-catalyzed cyclization reaction afforded the final polyaromatics. As the function of OLECs depends on the use of charged species, the formation of final naphthalene and carbazole containing polyaromatic salts was achieved either by the bis-methylation of nitrogen atoms in the heteroaryl substituents within the conjugated system, or by introducing alkyl side chains bearing charged imidazoliums. The final charged polyaromatics were tested by our collaborators at the School of Electronics and Computer Science (University of Southampton) for potential use in OLECs. Finally, short nitrogen-containing polyaromatics and carbazole-containing polyaromatics were synthesized via a Mallory type photochemically induced cyclization of stilbene-like precursors.

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Identifiers

ORCID for Richard Whitby: orcid.org/0000-0002-9891-5502

ORCID for David Harrowven: orcid.org/0000-0001-6730-3573

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