Synthesis, NMR, X-ray and UV/Vis characterization and preliminary luminescence study of some boron β-iminoenolates having 6-aminocoumarin moiety

Five coumarin-based polarized ethylenes (enaminoketones, enaminoester and enaminoamide) were prepared using the condensation of the parent β-dicarbonyl compounds with 6-aminocoumarin. Reaction of the polarized ethylenes with an appropriate source of trivalent boron gave corresponding boron β-iminoen...

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Published inJournal of organometallic chemistry Vol. 802; pp. 60 - 71
Main Authors Doušová, Hana, Šimůnek, Petr, Almonasy, Numan, Růžičková, Zdeňka
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 15.01.2016
Elsevier
Subjects
Boron
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Enaminone
Fluorescence
Iminoenolate
NMR
Physical Sciences
Science & Technology
X-ray
Fluorescence
Boron
NMR
X-ray
Iminoenolate
Enaminone
POLYMERS
4-COORDINATE ORGANOBORON COMPOUNDS
FLUORESCENT BF2 COMPLEXES
PHOTODYNAMIC THERAPY
KETOIMINATE
BODIPY DYES
LIGANDS
CHEMISTRY
BEARING
EMISSION
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Summary:Five coumarin-based polarized ethylenes (enaminoketones, enaminoester and enaminoamide) were prepared using the condensation of the parent β-dicarbonyl compounds with 6-aminocoumarin. Reaction of the polarized ethylenes with an appropriate source of trivalent boron gave corresponding boron β-iminoenolates having either BF2 or BPh2 fragment. The prepared iminoenolates were characterized by means of multinuclear magnetic resonance in solution, single-crystal X-ray diffraction and UV/Vis spectroscopy. A preliminary luminescence study of the iminoenolates as well as their parent enamines was done. The compounds exhibited fluorescence in a solid state as well as in a frozen 2-methyltetrahydrofuran at 77 K. Exploratory tests showed promising AIE/AIEE properties of the tested compounds. On the other hand, no fluorescence in a solution state (with one exception) was observed. Boron β-iminoenolates having coumarin-6-yl moiety on the nitrogen atom and BF2 or BPh2 fragment fluoresce both in solid state and in frozen 2-methyltetrahydrofuran at 77 K. No fluorescence was observed in solution. The fluorescence starts to appear in aggregation state after admixing their THF solutions with water. [Display omitted]
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2015.11.016