Yu. V. Revinskii

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

Novel derivatives of 1,2,4-triazol with benzthiazole fragment have been prepared, including Cu(II) and Be complexes. Their structure and spectral luminescent properties have been investigated. With ohydroxyphenylbenzthiazolyl-1,2,4-triazole as an example, the density functional theory has been applied to find the stable conformers with different structures of coordination nodes, stabilized by intramolecular hydrogen bonds between hydroxyl group hydrogen and either triazole of benzthiazole nitrogen.

Synthesis, structure, and luminescent properties of 2-[2-(9-anthryl)vinyl]quinolines

Previously unknown 2-[2-(9-anthryl)vinyl]quinolin-8-ol and 2-[2-(9-anthryl)vinyl]-8-methoxyquinoline were synthesized by condensation of 8-hydroxy(methoxy)-2-methylquinoline with 9-anthraldehyde in acetic anhydride, as well as by the Wittig reaction. The product structure was determined on the basis of their 1H NMR, IR, UV, and mass spectra and quantum-chemical calculations. 2-[2-(9-Anthryl)vinyl]-8-methoxyquinoline showed luminescence with a quantum yield φ of 0.25, which was considerably higher than that of its 8-hydroxy analog (φ = 0.067).

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

Bidentate ligand systems based on 2-hydroxyphenyloxadiazole attract strong interest due to application of metal complexes derived therefrom in photoand electroluminescent devices as blue-emitting chromophores, as well as electron-transporting materials that improve charge transfer balance in organic light-emitting diodes (OLEDs) [1, 2]. In addition, organic luminophores based on diphenyloxadiazoles exhibit an anomalously high Stokes shift (ASS), which favors increase in the light yield as a result of reduced self-absorption and minimizes liminophore photodegradation [3].

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

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 (λmax = 438–512 nm); however, only alkyl derivatives of 2-styryl-8-hydroxyquinoline possessed the high quantum yield (φ = 0.16–0.41).

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

a Southern Scientific Center, Russian Academy of Sciences, ul. Chekhova 41, Rostov-on-Don, 344006 Russia e-mail: mikhail@ipoc.rsu.ru b Southern Federal University, Rostov-on-Don, Russia c Institute of Arid Zones, Southern Scientific Centre, Russian Academy of Sciences, Rostov-on-Don, Russia d Scientific Research Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russia

Chemosensors based on N -(9-anthrylmethyl)-benzene-1,2-diamine

A number of N-(9-antrylmethyl)-N′-arylmethylidenebenzene-1,2-diamines and 1-(9-anthrylmethyl)-2-aryl-1H-benzimidazoles were synthesized by condensation of N-(9-anthrylmethyl)benzene-1,2-diamine with aromatic and heterocyclic aldehydes. Study on their luminescent properties and complexing ability showed that 2-{[2-(9-anthrylmethylamino)phenylimino]methyl}-5-methylphenol, 2-{[2-(9-anthrylmethylamino)phenylimino] methyl}-4-methoxyphenol, and 2-{[2-(9-anthrylmethylamino)phenylimino]methyl}-6-methoxy-4-nitrophenol are effective and highly selective chemosensors for H+ and Hg2+ ions.

Complexing properties of ambidentate benzo-15-crown-5-substituted azomethine ligands

Crown-containing azomethines and their zinc complexes were prepared. Examination of their structure by 1H and 7Li NMR and electronic spectroscopy showed that, in accordance with the concept of hard and soft acids and bases, the hard lithium cation coordinates to the crown ether fragment with the formation of mono-(Li) and binuclear (Li, Zn) complexes.

Absorption and luminescence spectra of 5-aryl-3-methyl-1,2,4-oxadiazoles and their chelate complexes with Zinc(II) and copper(II)

Abstract5-(2-Hydroxyphenyl)-3-methyl-1,2,4-oxadiazole and its O-methyl and O-acyl derivatives, as well as zinc(II) and copper(II) chelates, were synthesized. All these compounds showed luminescence with the emission maxima ranging from λ = 332 to 490 nm, but only 5-(2-methoxyphenyl)- and 5-(2-acetoxyphenyl)-3-methyl-1,2,4-oxadiazoles and zinc(II) complex of 5-(2-hydroxyphenyl)-3-methyl-1,2,4-oxadiazole were characterized by high luminescence quantum yield (φ = 0.308–0.452, 0.089–0.153, and 0.115–0.334, respectively). Stable conformers of 5-(2-hydroxyphenyl)-3-methyl-1,2,4-oxadiazole with different structures of the coordination entity were identified by DFT quantum chemical calculations.

Electrochemical and chemical synthesis and structure of adducts (CH3OH and H2O) of metal chelates of N,N,O tridentate pyrazole-containing Schiff base

Chemical and electrochemical synthesis of a series of cobalt(II), nickel(II), copper(II), and zinc(II) complexes of tridentate Schiff base (H2L), a product of condensation of N-(2-aminophenyl)-4-methylbenzenesulfonamide (2-tosylaminoaniline) with 1-phenyl-3-methyl-4-formylpyrazol-5-ol was accomplished. The structure and composition of metal-chelates were established by the C, H, N elemental analysis, IR, 1H NMR, EXAFS spectroscopy and magnetochemical data. The structures of all complexes were confirmed by of X-ray crystallography.

Benzoid-quinoid tautomerism of schiff bases and their structural analogs: LIII. Schiff bases derived from 5-hydroxy- and 5-hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehydes

Abstract4-Aryl(alkyl)iminomethyl-5-hydroxy-and 4-aryl(alkyl)iminomethyl-5-hydroxy-6-nitro-2,3-diphenyl-1-benzofurans were synthesized and were shown to exist in solution as equilibrium mixtures of benzoid and quinoid tautomers. The fraction of the quinoid form increases with rise in the solvent polarity and in going from N-aryl to N-alkyl derivatives; introduction of an electron-acceptor substituent (nitro group) into the 6-position of the benzofuran system also favors formation of the quinoid tautomer. Complex formation of alkali and alkaline-earth metal cations with the 5-hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehyde imine having a benzo-15-crown-5 fragment on the nitrogen atom is accompanied by specific changes in the luminescence spectrum and in the state of tautomeric equilibrium, so that this system may be regarded as tautomeric fluorogenic chemosensor for metal cations.