The effect of fluorination on the luminescent behaviour of 8-hydroxyquinoline boron compounds

Hellstrom, Sondra; Ugolotti, Juri; Britovsek, George J. P.; Jones, T. S.; White, Andrew J. P.

doi:10.1039/b712837a

Cited by 41 publications

(27 citation statements)

References 43 publications

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“…These values are lower than those reported for related diarylborinic 8-oxyquinolinates (ca. 37,38 In contrast to the case of 1 and 10, it was recently reported that the replacement of Ph 2 B with a (C 6 F 5 ) 2 B moiety in diarylboron diketonates resulted in the increase of λ em by ca. 2, 26 We have observed that the 1 H NMR chemical shifts of aldimine protons (CHvN) in 1-7 (solvent: acetone-d 6 ) correlate strongly (R 2 = 0.95) with Hammett σ p − constants of R′ substituents 34,35 attached to the salicydene fragment at the 6-position (Fig.…”

Section: Synthesis and Characterizationmentioning

confidence: 93%

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

et al. 2015

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A series of diarylborinic complexes with salicydeneaniline ligands bearing various functional groups at the 6-position have been synthesized in high yields by applying a straightforward one-pot multicomponent protocol. UV-Vis measurements revealed the influence of electronic character of substituents on the observed maximum of emission (λem). This has been confirmed by a relatively strong linear correlation (R(2) = 0.92) of λem with Hammett σp(+) constants. Such a correlation was investigated using a QTAIM analysis of the charge density distribution. Absorption and emission bands for the obtained systems span between 390-437 nm and between 506-590 nm, respectively, with quantum yields reaching 17%. Time-dependent UV-Vis absorption measurements revealed that diphenylborinic salicydeneaniline complexes undergo slow degradation in solution under ambient conditions. In contrast, the use of a naphthalene-based chromophore or the introduction of fluorinated phenyl groups at the boron atom resulted in stable systems.

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Section: Synthesis and Characterizationmentioning

confidence: 93%

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

et al. 2015

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“…2000 cd·m −2 and current efficiencies above 1 cd·A −1 . It should be stressed that such good parameters were achieved with diodes containing only 2 wt% of emitter in the matrix whereas in previous reports much higher emitter contents (above 10 wt%) were used 72. It may be the case that the promising optical properties of 1-5 are a consequence of a cooperation of two Q chromophores present in the molecular structure.…”

mentioning

confidence: 94%

Efficient 8-oxyquinolinato emitters based on a 9,10-dihydro-9,10-diboraanthracene scaffold for applications in optoelectronic devices

et al. 2015

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A detailed experimental characterization and theoretical evaluation of optical as well as other relevant physicochemical properties of a series of 9,10-dihydro-9,10-diboraanthracene bis(8-oxyquinolinates) and a few other related systems is reported. The obtained compounds exhibit green luminescence with quantum yields of emission up to 63% in CH 2 Cl 2 . Single crystal X-ray diffraction studies indicate that 9,10-dihydro-9,10-diboraanthracene complexes exist either as bent conformers (stabilized by a weak intramolecular CH…O interaction bringing two 8-oxyquinolinato ligands closer to each other) or symmetrical ones (bearing both ligands related by the centre of symmetry and separated one from the other). Theoretical calculations revealed that the LUMO levels are lower for the bent conformers than for the symmetrical ones. This suggests that the luminescent properties of the studied compounds are affected by their specific structural properties. The obtained compounds were used as emitters for the construction of organic light emitting diodes (OLEDs). The highest luminance of ca. 2,000 cd·m −2 was recorded for the device containing only 2.0 wt% of 1,6-difluoro-9,10-dihydro-9,10-diboraanthracene core in the poly(Nvinylcarbazole/2-t-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PVK:PBD) matrix. The fabricated OLEDs exhibit current efficiency in the range from 0.5 to 1.1 cd·A −1 .

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“…[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] Among the tetracoordinate boron compounds, boron dipyrromethene dyes ( Figure 1, A) [32][33][34][35] have been studied to a greater extent owing to their potential application in artificial light harvesters, fluorescent sensors, laser dyes, sensitizers for solar cells, and molecular photonic wires. Boron quinolate compounds are analogous to aluminum quinolato compounds ( Figure 1, B); [26,[36][37][38][39][40][41][42] the photophysical tuning of R 2 BQ compounds (Q = substituted quinolate) was recently studied by Wang and co-workers [40,41] and Jaekle and coworkers. [43][44][45][46] Schiff base boron compounds ( Figure 1, C) are yet another type of four-coordinate boron complex that has gained interest owing to their greater stability than tricoordinate boron compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Properties of Salicylaldimine‐Based Diboron Complexes

et al. 2013

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The effect of fluorination on the luminescent behaviour of 8-hydroxyquinoline boron compounds

Cited by 41 publications

References 43 publications

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

Efficient 8-oxyquinolinato emitters based on a 9,10-dihydro-9,10-diboraanthracene scaffold for applications in optoelectronic devices

Synthesis and Optical Properties of Salicylaldimine‐Based Diboron Complexes

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