Absorption spectra and nature of electron transitions in azomethine dyes as 6-derivatives of 2H-2-chromenone

Kachkovski, O.D.; Tolmachev, O.I.; Kobryn, Lesya; Bilaya, E. E.; Ganushchak, Mykola I.

doi:10.1016/j.dyepig.2004.02.008

Cited by 26 publications

(8 citation statements)

References 10 publications

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“…They were yellow to orange crystalline substances. The structure of compounds І-XXXVIII was confirmed by the 1 H NMR spectra (see Experimental), and physical constants of previously described compounds ІI, III, X, and XV coincided with published data [5][6][7]. The 1 H NMR spectra of the newly synthesized compounds were recorded from 0.08 M solutions in DMSO-d 6 at 25°C.…”

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confidence: 76%

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Schiff Bases Derived from 6-Amino-2H-chromen-2-one. Synthesis and 1H NMR Spectra

et al. 2005

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A number of 6-arylmethylideneamino-2H-chromen-2-ones were synthesized by reaction of 6-amino-2H-chromen-2-one with aromatic and heterocyclic aldehydes. A linear relation was revealed between the chemical shifts of the azomethine CH=N proton and protons in the chromene ring, on the one hand, and Hammett constants σ of the para substituents, on the other. Formation of intramolecular hydrogen bond in ortho-hydroxy derivatives induces a downfield shift of signals from protons in positions 3-5, 7, and 8 and CH=N proton (9-H) and upfield shift of the o-H signal (14-H). I, R 3 = Et 2 N; II, R 3 = Me 2 N; III, R 3 = HO; IV, R 3 = EtO; V, R 3 = MeS; VI, R 3 = Et; VII, R 3 = AcNH; VIII, R 3 = 5-carboxy-1-methylpyrazol-3-yl; IX, R 3 = BzO; X, R 3 = H; XI, R 3 = Cl; XII, R 3 = Br; XIII, R 3 = CN; XIV, R 3 = O 2 N; XV, R 1 = HO; XVI, R 1 = EtO; XVII, R 1 = F; XVIII, R 1 = Cl; XIX, R 1 = O 2 N; XX, R 1 = R 3 = Me; XXI, R 2 = R 3 = R 4 = MeO; XXII, R 2 = MeO, R 3 = HO; XXIII, R 2 = MeO, R 3 = PrO; XXIV, R 2 = MeO, R 3 = BzO; XXV, R 2 = MeO, R 3 = p-FBzO; XXVI, R 1 = MeO, R 4 = Br; XXVII, R 1 = HO, R 2 = R 4 = Cl; XXVIII, R 2 = O 2 N; XXIX, R 2 = O 2 N, R 3 = Cl; XXX, R 1 = Cl, R 4 = O 2 N; XXXI, R 1 = F, R 5 = Cl; XXXII, R 2 = MeO, R 3 = 5-carboxy-1-methylpyrazol-3-yl; XXXIII, X = 2-hydroxy-1-naphthyl; XXXIV, X = 9-anthryl; XXXV, X = 3-pyridyl; XXXVI, X = 2-hydroxy-6-methylquinolin-3-yl; XXXVII, X = 2-methylindol-3-yl; XXXVIII, X = 1,2-dimethylindol-3-yl; R i = H unless otherwise stated.Compounds of the coumarin series are fluorescent dyes and materials for dye lasers [1-4]. These compounds include N-arylmethylidene derivatives (Schiff bases) of 6-amino-2H-chromen-2-one, which were reported by us previously [5]. In order to study in detail their spectral parameters with regard to the nature of substituent in the arylmethylidene fragment, we have synthesized a number of new Schiff bases belonging to this series.Compounds І-XXXVIII were obtained by condensation of the corresponding aldehydes with 6-amino-2H-chromen-2-one in anhydrous alcohol or dioxane in the presence of a catalytic amount of piperidine on heating for 6 h under reflux. 6-Arylmethylideneamino-2H-chromen-2-ones І-XXXII were synthesized from substituted benzaldehydes, and Schiff bases XXXIIІ-XXXVIII, from polycyclic and heterocyclic aldehydes. The products were isolated and purified by standard procedures. They were yellow to orange crystalline substances. The structure of compounds І-XXXVIII was confirmed by the 1 H NMR spectra (see Experimental), and physical constants of previously described compounds ІI, III, X, and XV coincided with published data [5][6][7]. The 1 H NMR spectra of the newly synthesized compounds were recorded from 0.08 M solutions in DMSO-d 6 at 25°C. It seemed to be reasonable to compare their spectral parameters (i.e., chemical shifts and coupling constants) and correlate these parameters with their structure, specifically with the nature of R 1 -R 5 substituents in the phenyl ring. 8 7 6 5 O 3 4 O N 9 14 13 12 11 10 R 5 R 1 R 2 R 3 R 4

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confidence: 76%

“…These compounds include N-arylmethylidene derivatives (Schiff bases) of 6-amino-2H-chromen-2-one, which were reported by us previously [5]. In order to study in detail their spectral parameters with regard to the nature of substituent in the arylmethylidene fragment, we have synthesized a number of new Schiff bases belonging to this series.…”

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confidence: 99%

Schiff Bases Derived from 6-Amino-2H-chromen-2-one. Synthesis and 1H NMR Spectra

et al. 2005

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“…430 nm, were assigned to forbidden n ? p * transitions associated with the azomethine group [30,52,53].…”

Section: Synthesis and Characterisation Of The Schiff Base Ligands (2mentioning

confidence: 99%

“…These workers found that the complexes were active against bacterial strains but not particularly effective against C. albicans. Coumarin-derived Schiff bases are well known compounds and several reports have been written about their applications as dye and fluorescent agents [30,31]. Iminocoumarins have also been shown to exhibit anti-inflammatory, antibacterial and antifungal activities [32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Copper(II) complexes of coumarin-derived Schiff bases and their anti-Candida activity

Creaven

Devereux

Karcz

et al. 2009

Journal of Inorganic Biochemistry

101

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“…Both coumarins and vic-dioximes have been of considerable interest not only in academic investigations but also in industry due to their potentially wide applications [1][2][3][4]. Coumarin (2H-1-benzopyran-2-one) and coumarin derivatives, commercially significant group of organic fluorescent materials, are natural compounds and are important chemicals in the perfume, cosmetic, agrochemicals, insecticides, electroluminescent devices, laser dyes and pharmaceutical industrial production [3][4][5][6]. Recently, various fluorescent probes have been developed to study biological phenomena in living cells where fluorescence resonance energy transfer (FRET) has been used in many cases.…”

Section: Introductionmentioning

confidence: 99%

Coumarin-derivatized fluorescent vic-dioxime-type ligand and its complexes; the preparation, spectroscopy, and electrochemistry

Çamur

Bulut

Özkaya

et al. 2007

Transition Met Chem

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A new vic-dioxime bearing coumarin functionality, N¢ 1 ,N¢ 2 -Dihydroxy-N 1 ,N 2 -bis(4-methyl-2-oxo-2H-chromen-7-yl)oxalimidamid (LH 2 ), N,N-bis-[4-methylcoumarinyl]-diamino glyoxime (LH 2 ), and its mono-and dinuclear complexes {copper II , cobalt II , nickel II and uranyl II } have been reported. The fluorescence excitation and emission spectra of LH 2 and its complexes with metal ions were examined. It was observed that fluorescence and excitation emission intensity of LH 2 was quenched depending on complex formation with metal ions. The characterizations of all newly synthesized compounds were made by elemental analysis, 1 H-n.m.r, i.r., u.v.-vis., and l.c-m.s./m.s. data. Electrochemical behaviour of the ligand involving oxime and coumarine moieties, and its complexes with Ni II , Cu II , Co II and UO 2 II were investigated by cyclic voltammetry. The comparison of the electrochemical behaviour of the ligand with its complexes enabled us to identify metal-, oxime-and coumarine-based signals.

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Absorption spectra and nature of electron transitions in azomethine dyes as 6-derivatives of 2H-2-chromenone

Cited by 26 publications

References 10 publications

Schiff Bases Derived from 6-Amino-2H-chromen-2-one. Synthesis and 1H NMR Spectra

Schiff Bases Derived from 6-Amino-2H-chromen-2-one. Synthesis and 1H NMR Spectra

Copper(II) complexes of coumarin-derived Schiff bases and their anti-Candida activity

Coumarin-derivatized fluorescent vic-dioxime-type ligand and its complexes; the preparation, spectroscopy, and electrochemistry

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