Synthesis, structure, and spectral luminescent properties of novel 1,2,4-triazole derivatives containing benzthiazole group

Beldovskaya, A. D.; Душенко, Г. А.; Vikrishchuk, N. I.; Попов, Л. Д.; Revinskii, Yu. V.; Михайлов, И. Е.

doi:10.1134/s1070363213110200

Cited by 25 publications

(11 citation statements)

References 12 publications

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“…IIa showed blue-green luminescence (λ max = 438-512 nm) with fairly low quantum yield (φ = 0.001-0.012) due to the ESIPT process operative [6][7][8]. The luminescence of its methyl (IIb) and benzyl (IIc) derivatives was more efficient since the ESIPT process was restricted; the emission maximum was shifted towards shorter wavelength (λ max = 434-481 nm, φ = 0.16-0.41).…”

Section: -[2-(pyridine-4-yl)vinyl]quinoline-8-olmentioning

confidence: 99%

“…They form stable complexes with majority of metals and they are often used as precipitants for separation of metal cations [2], highly selective fluorescent chemosensors [3], biologically active compounds [4], and components of efficient electroluminescent materials for organic light-emitting diodes (OLEDs) [5]. Fluorescence of 8-hydroxyquinoline is weak due to the photo-initiated excitedstate intramolecular proton transfer (ESIPT) [6][7][8]; however, the proton transfer can be blocked via complexation with metal ions or the 8-hydroxyl group esterification, thus enhancing the fluorescence [9,10]. Electronic π-π*-transfer in 8-hydroxyquinoline and its metal complexes significantly depends on the electronic parameters of the substituents in the quinoline ring; hence, fine tuning of the optical parameters as well as electronic and hole transport properties is possible via chemical modification of the ligand.…”

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Synthesis and spectral-luminescence properties of 2-[2-(pyridin-4-yl)vinyl]quinolines

et al. 2015

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Condensation of 2-methylquinolines with 4-pyridinecarboxaldehyde in acetic acid anhydride has yielded 2-styryl-8-hydroxyquinoline along with its methyl and benzyl derivatives. Tosylation of 2-styryl-8-hydroxyquinoline has led to the corresponding p-toluenesulfonyloxy derivative. All the obtained compounds have revealed blue-green luminescence (λ max = 438-512 nm); however, only alkyl derivatives of 2-styryl-8-hydroxyquinoline possessed the high quantum yield (φ = 0.16-0.41). Keywords: 2-styryl-8-hydroxyquinoline, absorption spectrum, luminescence spectrum, quantum yield, organic luminophor 8-Hydroxyquinoline and its derivatives are among the universal ligands used in a wide range of practical applications [1]. They form stable complexes with majority of metals and they are often used as precipitants for separation of metal cations [2], highly selective fluorescent chemosensors [3], biologically active compounds [4], and components of efficient electroluminescent materials for organic light-emitting diodes (OLEDs) [5]. Fluorescence of 8-hydroxyquinoline is weak due to the photo-initiated excitedstate intramolecular proton transfer (ESIPT) [6-8]; however, the proton transfer can be blocked via complexation with metal ions or the 8-hydroxyl group esterification, thus enhancing the fluorescence [9, 10]. Electronic π-π*-transfer in 8-hydroxyquinoline and its metal complexes significantly depends on the electronic parameters of the substituents in the quinoline ring; hence, fine tuning of the optical parameters as well as electronic and hole transport properties is possible via chemical modification of the ligand. Moreover, introduction of certain substituents (for instance, styryl) at the ligand enhances thermal stability of the metal-ligand complexes and their solubility in organic media [11,12].Aiming to expand a range of the above-mentioned compounds and study their luminescent properties, novel 8-hydroxyquinoline ligand II with 2-(pyridine-4-yl)vinyl substituent at position 2 of the quinoline ring was prepared via condensation of 2-methylquinolines Ia-Ic with 4-pyridinecarboxaldehyde in acetic acid anhydride. Arylsulfonyloxyquinoline III was prepared via reaction of styrylquinoline IIa with p-toluenesulfonyl chloride in the presence of trimethylamine as base (Scheme 1).Structures of the prepared compounds IIa-IIc, III were elucidated taking into account the elemental analysis as well as IR, UV, 1 H, and 13 C NMR spectroscopy data. Furthermore, luminescent properties of the products were investigated. 1 H NMR spectra of styrylquinlolines IIa-IIc, III contained the vinyl protons signals at 7.23-7.60 and 7.43-7.70 ppm with spin-spin coupling constant of 16.0-17.5 Hz, indicating their trans-configuration and coinciding with the earlier reported data [13]. Electronic absorption spectra of the compounds contained long-wave bands maximums due to the π-π* transition at 323-375 nm; a small red shift (by 4-7 nm) of the

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Section: -[2-(pyridine-4-yl)vinyl]quinoline-8-olmentioning

confidence: 99%

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Synthesis and spectral-luminescence properties of 2-[2-(pyridin-4-yl)vinyl]quinolines

et al. 2015

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“…The absorption and fluorescence spectra were measured on a Cary Scan 100 spectrophotometer and a Cary Eclipse fluorescence spectrophotometer, respectively. The fluorescence quantum yields were determined relative to anthracene in acetonitrile [17].…”

Section: -(26-dimethoxyphenyl)-mentioning

confidence: 99%

Spectral Luminescent Properties of 2-Aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles

et al. 2018

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Abstract-2-Aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles were synthesized by cyclization reaction of benzoylbenzohydrazides in SOCl 2 , and their spectral luminescent properties were studied. The oxadiazoles containing phenyl or o-methoxyphenyl substituents in the position 2 were shown to luminesce with a high quantum yield in polar and nonpolar solvents. The replacement of these substituents by 2-hydroxyphenyl group led to oxadiazole intensely emitting only in highly polar aprotic DMSO.Keywords: 2,5-diaryl-1,3,4-oxadiazoles, luminescence, luminescence quantum yield, organic phosphors ISSN 1070-3632, Russian Journal of General Chemistry, 2018, Vol. 88, No. 2, pp. 338-341. © Pleiades Publishing, Ltd., 2018. Original Russian Text © I.E. Mikhailov, Yu.M. Artyushkina, G.A. Dushenko, O.I. Mikhailova, Yu.V. Revinskii, V.I. Minkin, 2018, published in Zhurnal Obshchei Khimii, 2018 1,3,4-Oxadiazoles and their derivatives belong to one of the most intensively studied classes of fivemembered nitrogen-containing heterocycles characterized by good synthetic accessibility and high structural variability, as well as by wide range of practical applicability. These compounds have diverse biological activity [1] and are extensively used in various fields of medicinal chemistry [2] and pesticide chemistry [3]. Also, they possess interesting spectral luminescent properties making them suitable for the preparation of widely demanded organic [4][5][6][7] and metal complex-based [8,9] phosphors. LETTERS TO THE EDITORFor expanding the range of compounds of this class and for studying their spectral luminescent properties we applied here the reaction of hydrazides 1a-1c with 2,6-dimethoxybenzoic acid chloride in the presence of triethylamine to obtain benzoylbenzohydrazides 2a-2c whose subsequent cyclization with thionyl chloride led to 2-aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles 3a-3c (Scheme 1).In the absorption spectra of oxadiazoles 3a-3c the maximum of the long-wave band due to π→π* electron transitions is observed within the 256-316 nm range, consistent with their benzenoid structure. The luminescence spectra of oxadiazole 3b in isooctane, toluene, and acetonitrile contain two bands: a shortwave band (λ m fl ax 353-378 nm, φ 0.001-0.012) which has a normal Stokes shift (3019-4992 cm

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“…A significant increase in the luminescence quantum yield of oxadiazole I derivatives was obtained by replacing the benzoyl group with acyl moiety and by increasing the energy of n-π*-levels in IIa (acetonitrile, λ f m l ax 353 nm, φ 0.91; isooctane , λ f m l ax 351 nm, φ 0.95). It should be noted that oxadiazole I luminesces with a low quantum yields (λ f m l ax 350-503 nm, φ 0.008-0.012) [6], which is caused by nonradiative deactivation of its excited state by ESIPT-mechanism [9,10].…”

Section: Mikhailov Et Al 204mentioning

confidence: 99%

Synthesis and luminescent properties of 2-[2′-acyl(benzoyl)oxyphenyl]-5-(4″-nonylphenyl)-1,3,4-oxadiazole

et al. 2015

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Synthesis, structure, and spectral luminescent properties of novel 1,2,4-triazole derivatives containing benzthiazole group

Cited by 25 publications

References 12 publications

Synthesis and spectral-luminescence properties of 2-[2-(pyridin-4-yl)vinyl]quinolines

Synthesis and spectral-luminescence properties of 2-[2-(pyridin-4-yl)vinyl]quinolines

Spectral Luminescent Properties of 2-Aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles

Synthesis and luminescent properties of 2-[2′-acyl(benzoyl)oxyphenyl]-5-(4″-nonylphenyl)-1,3,4-oxadiazole

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