14752-00-2Relevant articles and documents
Theoretical and experimental studies on the fluorescence properties of aluminum(III), cadmium(II), zinc(II), and copper(II) complexes of substituted 8-hydroxyquinoline
Hongli, Chen,Hongrui, Cheng,Menglin, Ma,Qingrong, Sun,Weiqing, Yang,Yuanyuan, Zhang
, p. 623 - 634 (2020/12/14)
Fifty-five 8-hydroxyquinoline (8-HQ) derivatives are synthesized and the corresponding aluminum(III), cadmium(II), copper(II), and zinc(II) metal complexes are prepared and their fluorescent activities are evaluated. The results indicate that the aluminum complexes have the best fluorescence properties, followed by zinc and cadmium complexes, while almost no fluorescence is observed with the copper complexes. The relationship between the fluorescence properties and complex structure is summarized and a predictive three-dimensional quantitative structure–property relationship model is established using the multifit molecular alignment rule of Sybyl program. With the introduction of groups at the C-2 position or electron-withdrawing groups to the 8-hydroxyquinoline framework, fluorescence wavelength blue shifts are observed with the zinc, aluminum, and cadmium complexes. At the same time, a red shift of the fluorescence emission wavelength is detected for the aluminum and zinc complexes when C-5 of 8-hydroxyquinoline was substituted with halogens or a methyl group. Moreover, the zinc, cadmium, and aluminum complexes with 2,4-dimethyl substituents on the 8-hydroxyquinoline all show good fluorescence properties. The highest occupied molecular orbital and lowest unoccupied molecular orbital energies of the complexes are also calculated and the fluorescence properties of the metal complexes are analyzed from the viewpoint of molecular orbitals.
Effects of systematic methyl substitution of metal (III) tris(n-methyl-8-quinolinolato) chelates on material properties for optimum electroluminescence device performance
Sapochak,Padmaperuma,Washton,Endrino,Schmett,Marshall,Fogarty,Burrows,Forrest
, p. 6300 - 6307 (2007/10/03)
We relate the chemical structure of a series of methyl (Me) substituted group III metal tris(8-quinolinolato) chelates (nMeq3M: n = 0, 3, 4, 5; M = Al3+, Ga3+) to their photoluminescence (PL), electroluminescence, and thermal properties. Methylation of the 8-quinolinol ligand at the 3 or 4 position (pyridyl ring) results in a factor of 1.4 and 3.0 enhancement of PL quantum efficiency (OPL), respectively, whereas methylation at the 5 position (phenoxide ring) results in a factor of ～ 3.0 decrease in PL relative to the unsubstituted analogue. Electroluminescent quantum efficiencies of undoped organic light-emitting devices using the aluminum tris(8-quinolinolato) chelates are 1, 0.45, 1.4, and 0.80% for unsubstituted 5-, 4-, and 3-methyl-8-quinolinol ligands, respectively. Devices made with the latter two ligands have a higher operating voltage to generate the same current density. Similar trends were observed for methylation of gallium tris(8-quinolinolato) chelates. We relate these results to the thermal properties of the compounds measured by simultaneous differential scanning calorimetry and thermal gravimetric analysis. The C-4 methylated derivatives exhibit ～60 °C lower crystalline melting points than all other derivatives, indicating the weakest cohesive forces between molecules. Unlike Alq3, both the C-4 and C-5 methylated derivatives show no recrystallization of the glassy state below 500 °C and exhibit ～-20-25 °C higher glass transition temperatures. We infer that methylation of the 8-quinolinol ligand reduces intermolecular interactions and consequently impedes charge transport through the film.
