1379655-24-9Relevant academic research and scientific papers
BORON-CONTAINING CYCLIC EMISSIVE COMPOUNDS AND COLOR CONVERSION FILM CONTAINING THE SAME
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Page/Page column 96, (2020/10/21)
The present disclosure relates to novel photoluminescent complexes comprising a BODIPY moiety covalently bonded to a blue light absorbing moiety, a color conversion film comprising the photoluminescent complex, and a back-light unit using the same.
Diethyl (biscyclohexano)BODIPY dicarboxylates. Chelation of alkaline-earth metal ions and sensor properties
Tikhomirova,Khoroshutin,Anisimov
, p. 229 - 239 (2014/04/17)
meso-Aryl-substituted (biscyclohexano)bis(ethoxycarbonyl)BODIPY [aryl = phenyl, 3,4-dimethoxyphenyl, and 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13- benzopentaoxacyclopentadecin-15-yl-(m-{benzo-15-crown-5}-yl)] were synthesized. The effect of alkaline-earth metals on the absorption and fluorescence spectra of these compounds was investigated. In all compounds along with the mechanism of the photoinduced electron transfer (PET), well-known for the crown-containing BODIPY-based sensors, one more response pattern is observed. The large excess of Ca2+ and Ba2+ ions in the system leads to the changes both in the UV-Vis and emission spectra. The complex formation results in the decrease of emission intensity and in its red shift. Besides, a new longwave absorption band appears in the UV-Vis spectrum of the BODIPY-metal ion complex. The formation constants of the complexes corresponding to this response pattern is about 100 times less than the formation constant of Ca2+-crown ether complex. 1H, 13C, 11B, and 19F NMR spectra, the results of quantum-chemical calculations, and their comparison with the literature data of X-ray diffraction study suggest that the binding of Ca2+ and Ba2+ ions occurs in the cavity formed by the fluorine atoms and the carbonyl oxygen atoms of the ester groups.
Synthesis, computational modeling, and properties of benzo-appended BODIPYs
Uppal, Timsy,Hu, Xiaoke,Fronczek, Frank R.,Maschek, Stephanie,Bobadova-Parvanova, Petia,Vicente, M. Graca H.
, p. 3893 - 3905 (2012/05/20)
A series of new functionalized mono- and dibenzo-appended BODIPY dyes were synthesized from a common tetrahydroisoindole precursor following two different synthetic routes. Route A involved the assembly of the BODIPY core prior to aromatization, while in Route B the aromatization step was performed first. In general, Route A gave higher yields of the target dibenzo-BODIPYs, due to the ease of aromatization of the BODIPYs compared with the corresponding dipyrromethenes, probably due to their higher stability under the oxidative conditions (2,3-dichloro-5,6-dicyano-1,4-benzoquinone in refluxing toluene). However, due to the slow oxidation of highly electron-deficient BODIPY 3 c bearing a meso-C6F5 group, dibenzo-BODIPY 4 c was obtained, in 35 % overall from dipyrromethane, only by Route B. Computational calculations performed at the 6-31G(d,p) level are in agreement with the experimental results, showing similar relative energies for all reaction intermediates in both routes. In addition, BODIPY 3 c had the highest molecular electrostatic potential (MEPN), confirming its high electron deficiency and consequent resistance toward oxidation. X-ray analyses of eight BODIPYs and several intermediates show that benzannulation further enhances the planarity of these systems. The π-extended BODIPYs show strong red-shifted absorptions and emissions, about 50-60 nm per benzoannulated ring, at 589-658 and 596-680 nm, respectively. In particular, db-BODIPY 4 c bearing a meso-C 6F5 group showed the longest λmax of absorption and emission, along with the lowest fluorescence quantum yield (0.31 in CH2Cl2); on the other hand monobenzo-BODIPY 8 showed the highest quantum yield (0.99) of this series. Cellular investigations using human carcinoma HEp2 cells revealed high plasma membrane permeability for all dibenzo-BODIPYs, low dark- and photo-cytotoxicities and intracellular localization in the cell endoplasmic reticulum, in addition to other organelles. Our studies indicate that benzo-appended BODIPYs, in particular the highly stable meso-substituted BODIPYs, are promising fluorophores for bioimaging applications. Two synthetic routes to benzo- BODIPYs from a pyrrolic precursor were investigated. Computational calculations showed similar relative energies for all reaction intermediates and products in both routes. X-ray analyses indicated that benzannulation enhances the planarity of the BODIPY core (see figure). The benzo-BODIPYs show red-shifted absorptions and emissions, ca. 50-60 nm per benzoannulated ring, and high fluorescence quantum yields. Copyright
Biscyclohexane-annulated diethyl dipyrrindicarboxylates: Observation of a dipyrrin form with absent visible absorption
Tikhomirova, Ksenia,Anisimov, Alexander,Khoroshutin, Andrey
experimental part, p. 2201 - 2207 (2012/06/29)
A series of 2,3;7,8-biscyclohexano-fused diethyl 5-aryldipyrrin-1,9- dicarboxylates have been synthesized [aryl = phenyl, 3,4-dimethoxyphenyl and 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine-15-yl (m-benzo-15-crown-5)]. The obtain
