1386987-99-0

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 62-53-3 aniline 
• 4089-09-2 N-pyrrol-2-ylmethylene-aniline 
• 98-80-6 phenylboronic acid 
• 960-71-4 triphenylborane 

Relevant academic research and scientific papers

Method for Preparing Four-Coordinated Organic Boron Compound

The present invention relates to a method for preparing a four-coordinated organic boron compound, and more specifically, to a method for preparing various and widespread four-coordinated organic boron compounds by directly using an aryl, heteroaryl, or vinyl-functional boronic acid, boroxine, or borate compound as a starting material and adding the compound to any bidentate N,O-ligand, O,O-ligand, or N,N-ligand.

Tunable fluorophores based on 2-(N-Arylimino)pyrrolyl chelates of diphenylboron: Synthesis, structure, photophysical characterization, and application in OLEDs

Reactions of 2-(N-arylimino)pyrroles (HNC4H3C(H)=N- Ar) with triphenylboron (BPh3) in boiling toluene afford the respective highly emissive N,N-boron chelate complexes, [BPh2{κ 2N,N-NC4H3C(H)=N-Ar}] (Ar=C6H 5 (12), 2,6-Me2-C6H3 (13), 2,6-iPr2-C6H3 (14), 4-OMe-C6H 4 (15), 3,4-Me2-C6H3 (16), 4-F-C6H4 (17), 4-NO2-C6H4 (18), 4-CN-C6H4 (19), 3,4,5-F3-C 6H2 (20), and C6F5 (21)) in moderate to high yields. The photophysical properties of these new boron complexes largely depend on the substituents present on the aryl rings of their N-arylimino moieties. The complexes bearing electron-withdrawing aniline substituents 17-20 show more intense (e.g., φf=0.71 for Ar=4-CN-C6H4 (19) in THF), higher-energy (blue) fluorescent emission compared to those bearing electron-donating substituents, for which the emission is redshifted at the expense of lower quantum yields (φf=0.13 and 0.14 for Ar=4-OMe-C6H4 (15) and 3,4-Me2-C6H3 (16), respectively, in THF). The presence of substituents bulkier than a hydrogen atom at the 2,6-positions of the aryl groups strongly restricts rotation of this moiety towards coplanarity with the iminopyrrolyl ligand framework, inducing a shift in the emission to the violet region (λmax=410-465-nm) and a significant decrease in quantum yield (φf=0.005, 0.023, and 0.20 for Ar=2,6-Me2-C6H3 (13), 2,6-iPr 2-C6H3 (14), and C6F5 (21), respectively, in THF), even when electron-withdrawing groups are also present. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations have indicated that the excited singlet state has a planar aryliminopyrrolyl ligand, except when prevented by steric hindrance (ortho substituents). Calculated absorption maxima reproduce the experimental values, but the error is higher for the emission wavelengths. Organic light-emitting diodes (OLEDs) have been fabricated with the new boron complexes, with luminances of the order of 3000-cdm-2 being achieved for a green-emitting device. Fluorescent N,N-boron chelate complexes: Mononuclear boron complexes of 2-(N-arylimino)pyrrolyl emit violet to bluish-green colors in solution (see figure, ITO=indium tin oxide, PEDOT:PSS=poly(3,4- ethylenedioxythiophene):poly(styrene sulfonic acid)), depending on the substituents on the N-aryl group. Organic light-emitting diodes have been successfully fabricated with the new boron complexes, achieving luminances of the order of 3000-cdm-2.

MONO-AND POLYNUCLEAR BORON IMINOPYPROLYL COMPLEXES: METHODS OF PREPARATION AND USE AS LUMINESCENT MATERIALS

The current invention is concerned with new mono- and polynuclear tetracoordinate boron complexes containing chelating iminopyrrolyl ligands, with the general molecular structure (I), which possess photoluminescent and electroluminescent properties. Upon irradiation, these compounds emit light in a wide range, from violet to red, depending on their molecular characteristics. This invention is also concerned with the application of these new compounds in luminescent devices.

Syntheses and photophysical properties of new iminopyrrolyl boron complexes and their application in efficient single-layer non-doped OLEDs prepared by spin coating

Efficient non-doped OLEDs have been achieved using new binuclear tetracoordinate organoboron complexes containing 2-(N-aryl)formiminopyrrolyl ligands. The Royal Society of Chemistry.