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

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 substituent...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-03, Vol.13 (11), p.3268-3279
Main Authors: Wesela-Bauman, Grzegorz, Urban, Mateusz, Luliński, Sergiusz, Serwatowski, Janusz, Woźniak, Krzysztof
Format: Article
Language:English
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob02545h