Rearrangement of cyclotriveratrylene (CTV) diketone: 9,10-diarylanthracenes with OLED applications.

TitleRearrangement of cyclotriveratrylene (CTV) diketone: 9,10-diarylanthracenes with OLED applications.
Publication TypeJournal Article
Year of Publication2013
AuthorsSarsah SRS, Lutz MR, Zeller M, Crumrine DS, Becker DP
JournalThe Journal of organic chemistry
Volume78
Issue5
Pagination2051-8
Date Published2013 Mar 1
Abstract

Electroluminescent 9,10-diaryl anthracenes have been shown to be promising host and hole-transporting materials in organic electroluminescence due to their high thermal stability, electrochemical reversibility, and wide band gap useful for organic light-emitting diodes (OLEDs), especially blue OLEDs. Oxidation of cyclotriveratrylene (CTV) to the corresponding diketone and subsequent bromination resulted in an unexpected rearrangement to a highly functionalized 9-aryl-10-bromoanthracene derivative, which was employed in Suzuki couplings to synthesize a series of 9,10-diaryl compounds that are structural analogues of anthracene derivatives used in the preparation of OLEDs but are more highly functionalized, including electron-donating methoxy groups in addition to substitution by a carboxylic acid moiety. The UV/fluorescence solution spectra show strong emissions at 446, 438, and 479 nm, respectively, for the anthracene 10-phenyl, 10-naphthyl, and 10-pyrenyl adducts containing a benzoic acid functional group, whereas the analogues bearing the hydroxymethylene moiety from reduction of the benzoic acid to the corresponding alcohols gave much shorter emission wavelengths of 408, 417, and 476 nm, respectively, and had somewhat higher quantum yields, suggesting they are better candidates for OLED applications.

DOI10.1016/j.autrev.2012.10.007
Alternate JournalJ. Org. Chem.