Spectral luminescent properties of 2-(2-hydroxyphenyl)-5-methyl-1,3,4-oxadiazole and its acetyl(benzoyl)oxy derivatives

Михайлов, И. Е.; Artyushkina, Yu. M.; Душенко, Г. А.; Михайлова, О. И.; Revinskii, Yu. V.; Буров, Олег Н.

doi:10.1134/s1070428016110270

Cited by 11 publications

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“…Oxadiazoles 3a and 3c where an ESIPT process is impossible because of the absence of a mobile proton of the phenolic OH group emit intensely in a closely adjacent spectral region (λ m fl ax 352-363 nm, φ 0.11-0.33). Similar spectral behavior was previously observed in 1,3,4-oxadiazoles structurally similar to compounds 3a-3c [11][12][13][14][15].…”

Section: Spectral Luminescent Properties 339supporting

confidence: 85%

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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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Section: Spectral Luminescent Properties 339supporting

confidence: 85%

“…1 H (250.13 MHz) and 13 C (62.90 MHz) NMR spectra were obtained on a Bruker DPX-250 instrument. The absorption and fluorescence spectra were measured on a Cary Scan 100 spectrophotometer and a Cary Eclipse fluorescence spectrophotometer, respectively.…”

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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“…1,3,4-Oxadiazoles and their derivatives exhibit strong and diverse biological activity [1] as well as spectral luminescent properties enabling the preparation of fluorescent and phosphorescent luminophors [2][3][4][5], organic semiconductors, and other materials for modern optoelectronics [6] on their basis. Chelate complexes with oxadiazol ligands are widely used as metal complex luminophors [7,8] as well as emission and electron-transport materials for organic and light emitting diodes (OLED) [9].…”

Section: Spectral Luminescent Properties Of 3-[5-(4-methoxyphenyl)-1mentioning

confidence: 99%

Spectral Luminescent Properties of 3-[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]acrylic Acid and Its Complex with Zn(II)

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Solvatochromic analysis and DFT computational study of N-(hexyl)-N-(5-(3-hydroxynaphthyl-2-yl)-1,3,4-oxadiazol-2-yl)amine

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2019

Appl. Phys. A

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Spectral luminescent properties of 2-(2-hydroxyphenyl)-5-methyl-1,3,4-oxadiazole and its acetyl(benzoyl)oxy derivatives

Cited by 11 publications

References 15 publications

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

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

Spectral Luminescent Properties of 3-[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]acrylic Acid and Its Complex with Zn(II)

Solvatochromic analysis and DFT computational study of N-(hexyl)-N-(5-(3-hydroxynaphthyl-2-yl)-1,3,4-oxadiazol-2-yl)amine

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