Synthesis and luminescence properties of 2-(2-benzoyloxyphenyl)-5-aryl-1,3,4-oxadiazoles

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

doi:10.1134/s1070428013120312

Cited by 25 publications

(7 citation statements)

References 6 publications

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“…Conjugated polyaromatic systems such as fluorene, [15,16] carbazole, [17][18][19] coumarin, [20,21] pyrene, [22,23] substituted thiophenes, [24,25] and 1,3,4-oxadiazoles [26,27] have long established themselves as valuable fluorescent scaffolds. At the same time, 1,2,4-oxadiazole derivatives as a basis for luminescent materials have been studied much less.…”

Section: Introductionmentioning

confidence: 99%

2‐(1,2,4‐Oxadiazol‐5‐yl)aniline as a New Scaffold for Blue Luminescent Materials

et al. 2022

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Condensation of amidoximes 1 with isatoic anhydrides 2 or esters 3 in NaOH/DMSO medium afforded to substituted 1,2,4oxadiazolyl anilines. The compounds synthesized can exhibit luminescence, the presence and efficiency of which depends on the position of the amino group in these aminophenyl 1,2,4-oxadiazol derivatives. The best luminophores are 2-(ortho-aminophenyl) 1,2,4-oxadiazoles. More than 20 examples of the new organic luminophores were synthesized and studied. The effect of the luminophore structure on the emission band and on the quantum yield indicates that a luminescent scaffold has been obtained.

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Section: Introductionmentioning

confidence: 99%

2‐(1,2,4‐Oxadiazol‐5‐yl)aniline as a New Scaffold for Blue Luminescent Materials

et al. 2022

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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)

et al. 2018

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“…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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Synthesis and luminescence properties of 2-(2-benzoyloxyphenyl)-5-aryl-1,3,4-oxadiazoles

Cited by 25 publications

References 6 publications

2‐(1,2,4‐Oxadiazol‐5‐yl)aniline as a New Scaffold for Blue Luminescent Materials

2‐(1,2,4‐Oxadiazol‐5‐yl)aniline as a New Scaffold for Blue Luminescent Materials

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

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

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