Syntheses, Structures, and Luminescent Properties of Dipyridylamine-Functionalized Anthracene and Its Complexes

Abstract

A novel multidentate ligand with 2,2′-dipyridylamine functionalities, 1,8-bis­[4-(2,2′-dipyridylamino)­phenylacetylenyl]­anthracene (<b>1</b>), has been synthesized through a double Sonogashira coupling reaction and characterized by NMR spectroscopic, elemental, and X-ray diffraction analyses. Compound <b>1</b> can bind to either one metal center as a tetradentate ligand or two metal centers as a double-bidentate ligand. In the double-bidentate mode, the distance between the two metal centers may vary significantly. Compound <b>1</b> displays bright blue luminescence in the solid state and in solution with a quantum efficiency of 64% relative to 9,10-diphenylanthracene. While the dirhodium complex of <b>1</b> shows no luminescence, the two zinc complexes of <b>1</b> display blue luminescence with quantum efficiencies slightly lower than that of <b>1</b>. Organic light-emitting devices (OLEDs) using <b>1</b> as the emitter show a maximum current efficiency of 7 cd/A