Syntheses, structures, and luminescent properties of dipyridylamine-functionalized anthracene and its complexes.
A novel multidentate ligand with 2,2'-dipyridylamine functionalities, 1,8-bis[4-(2,2'-dipyridylamino)phenylacetylenyl]anthracene (1), has been synthesized through a double Sonogashira coupling reaction and characterized by NMR spectroscopic, elemental, and X-ray diffraction analyses. Compound 1 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 1 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 1 shows no luminescence, the two zinc complexes of 1 display blue luminescence with quantum efficiencies slightly lower than that of 1. Organic light-emitting devices (OLEDs) using 1 as the emitter show a maximum current efficiency of 7 cd/A.
Davenport Chemical Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Runyu
R
Tan
Zhi-Bin
ZB
Wang
Yu
Y
Li
Daniel J
DJ
Kozera
Zheng-Hong
ZH
Lu
Datong
D
Song
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000737:chemistry; D000873:Anthracenes / Q000138:chemical synthesis / Q000737:chemistry*; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D049449:Luminescence; D008958:Models, Molecular; D015394:Molecular Structure
D000873:Anthracenes; D056831:Coordination Complexes; D008024:Ligands; D015082:2,2'-Dipyridyl; C034020:anthracene; C048062:2,2'-dipyridylamine