Spectral and energetic transformation of femtosecond light impulses in the Eu3+ complex with dehydroacetic acid

Hanuza, J.; Ptak, Maciej; Lisiecki, Radosław; Janczak, Jan; Kwocz, Agnieszka; Kucharska, E.; Roszak, Szczepan; Ryba‐Romanowski, W.; Mączka, Mirosław; Hermanowicz, K.; Macalik, L.

doi:10.1016/j.jlumin.2018.02.067

Cited by 5 publications

(3 citation statements)

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“…These are colored substances that form complexes with metals [15] and boron [16]. Metal complexes have widely studied not only with dehydroacetic acid [17][18][19] but also Some of these compounds contain β-keto-enol or other fragments that may be promising to inorganic chemists as ligands. For example, the interaction of dehydroacetic acid with aromatic aldehydes by the Knoevenagel reaction produces the corresponding chalcones [9][10][11][12][13][14].…”

Section: Synthesis and Properties Of Chalcones Based On Dehydroacetic Acidmentioning

confidence: 99%

“…Metal complexes have also been widely studied not only with dehydroacetic acid [17][18][19] but also with its derivatives -Schiff bases [20][21][22][23][24][25] and other various O, N, S donor ligands [26][27][28]. For dehydroacetic acid and its derivatives, antimicrobial [15,29], antitumor [30,31], antiviral, in particular, anti-HIV activity [16,32,33], etc., are widely studied.…”

Section: Synthesis and Properties Of Chalcones Based On Dehydroacetic Acidmentioning

confidence: 99%

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Synthesis and Properties of Chalcones Based on Dehydroacetic Acid

Tretyakova¹,

Chernii

Fedosova

et al. 2021

Ukr. Chem. Journ.

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The Knoevenagel condensation reaction between dehydracetic acid and aromatic aldehydes is described in this work. The reaction is carried out directly between dehydroacetic acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the Knoevenagel reaction based on dehydroacetic acid and various aldehydes were determined. Twenty-one chalcones with substituents of different nature were synthesized. The composition and structure of the obtained compounds were determined. All characteristic signals of chalcones are present in the 1H NMR spectra of the obtained compounds registered in CDCl3 and DMSO-d6: OH groups in the range of 18.7–16.5 ppm, CH proton – 6.3–5.9 ppm, and methyl group of the pyran cycle 2.3–2.2 ppm. The corresponding signals of methine protons and aryl substituents are also present in the spectra. The most sensitive to solvent changes is the OH proton bound by an intramolecular hydrogen bond to the carbonyl group of the pyran ring. Signals in DMSO are usually shifted by 0.1–1.0 ppm in a stronger field compared to CDCl3 for dehydroacetic acid and chalcones based on it. CH proton signals are shifted by approximately 0.3 ppm in a weaker field, and the signals of the protons of the methyl group are almost insensitive to the solvent. The optical properties of obtained compounds were investigated in DMF, MeOH, MeCN. The synthesized chalcones absorb light in the visible range 330–490 nm with molar extinction coefficients of 3.5–4.5. The solvatochromic effects for most of them are weak – the position of the maximum changes by less than 10 nm. The electron-donor substituents in the phenyl ring (-NMe2 and -NEt2) shift the absorption maximum bathochromically by almost 100 nm compared to others in all investigated solvents.

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Section: Synthesis and Properties Of Chalcones Based On Dehydroacetic Acidmentioning

confidence: 99%

Section: Synthesis and Properties Of Chalcones Based On Dehydroacetic Acidmentioning

confidence: 99%

Synthesis and Properties of Chalcones Based on Dehydroacetic Acid

Tretyakova¹,

Chernii

Fedosova

et al. 2021

Ukr. Chem. Journ.

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“…The interaction of DHA with aromatic aldehydes leads to the formation of halcones [26,27], which serve as starting compounds to obtain alkylamino-βketoenoles. Another feature of DHA and some of its derivatives is their ability to form coordination complexes with metals [28][29][30]. In the case of metals with high coordination numbers, the formation of mixed-ligand DHA complexes with 8-hydroxy quinoline [31] and β-diketones [32] is possible.…”

Section: Introductionmentioning

confidence: 99%

Modification of insulin amyloid aggregation by Zr phthalocyanines functionalized with dehydroacetic acid derivatives

et al. 2021

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Amyloid fibrils are widely studied both as target in conformational disorders and as basis for the development of protein-based functional materials. The three Zr phthalocyanines bearing dehydroacetic acid residue (PcZr(L1)2) and its condensed derivatives (PcZr(L2)2 and PcZr(L3)2) as out-of-plane ligands were synthesized and their influence on insulin fibril formation was studied by amyloid-sensitive fluorescent dye based assay, scanning electron microscopy, fluorescent and absorption spectroscopies. The presence of Zr phthalocyanines was shown to modify the fibril formation. The morphology of fibrils formed in the presence of the Zr phthalocyanines differs from that of free insulin and depends on the structure of out-of-plane ligands. It is shown that free insulin mostly forms fibril clusters with the length of about 0.3–2.1 μm. The presence of Zr phthalocyanines leads to the formation of individual 0.4–2.8 μm-long fibrils with a reduced tendency to lateral aggregation and cluster formation (PcZr(L1)2), shorter 0.2–1.5 μm-long fibrils with the tendency to lateral aggregation without clusters (PcZr(L2)2), and fibril-like 0.2–1.0 μm-long structures (PcZr(L3)2). The strongest influence on fibrils morphology made by PcZr(L3)2 could be explained by the additional stacking of phenyl moiety of the ligand with aromatic amino acids in protein. The evidences of binding of studied Zr phthalocyanines to mature fibrils were shown by absorption spectroscopy (for PcZr(L1)2 and PcZr(L2)2) and fluorescent spectroscopy (for PcZr(L3)2). These complexes could be potentially used as external tools allowing the development of functional materials on protein fibrils basis.

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