I. E. Tolpygin

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.

New ionochromic azomethinimine chemosensors

A reaction of 5-phenylpyrazolidin-3-one with hydroxy-substituted aromatic aldehydes led to azomethinimines, the representatives of a new class of chemosensors exhibiting ionochromic properties. Electron spectroscopy was used to identify efficient chemosensors toward Cu2+ cations and F– anions.

11-R-dibenzo[b,e][1,4]diazepin-1-ones, the chemosensors for transition metal cations

A series of 11-R-dibenzo[b,e][1,4]diazepin-1-ones was synthesized. The luminescence, complex formation, and redox properties of these compounds were investigated. The 11-(anthracen-9-yl)-3,3-dimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one was found to be an effective and selective fluorescent chemosensor for Cd2+ cations.

Chemosensor properties of mono- and bisthioureas based on 9-anthrylmethyl-substituted alkylamines and diamines

Mono- and bisthioureas were synthesized based on N-(9-anthrylmethyl)-substituted alkylamines and diamines. Their luminescent and complexing properties were studied by the electronic, IR, and NMR 1H spectroscopy. N-(9-Anthrylmethyl)-N-(6-{9-anthrylmethyl[(phenylamino)carbothioyl]amino}hexyl)-N′-phenylthiourea was shown to be a highly effective fluorescent chemosensor for Hg2+ cations.

Chemosensors based on N-(2-aminophenyl)-N-(9-anthrylmethyl)amine: II

A series of N-(9-anthrylmethyl)arylimines was prepared by condensation of N-(2-aminophenyl)-N-(9-anthrylmethyl)amine with aromatic aldehydes. The study of the luminescent and complexing properties of compounds obtained showed that 2-{[2-(9-anthrylmethylamino)phenylimino]methyl}-1-naphthol and 1-{[2-(9- anthrylmethylamino)phenylimino]methyl}-6-bromo-2-naphthol were efficient highly selective chemosensors of cations Hg2+.

Effective pH sensors based on 1-(anthracen-9-ylmethyl)-1H-benzimidazol-2-amine

1-(Anthracen-9-ylmethyl)-1H-benzimidazol-2-amine was synthesized by alkylation of benzimidazol-2-amine with 9-chloromethylanthracene, and a series of azomethines based on it was obtained. Spectral investigations of the 9-anthrylmethylbenzimidazole derivatives revealed their high chemosensor activity with respect to hydrogen cations. Quantum-chemical investigation of the structures obtained showed that they possess high proton affinity and can be regarded as analogs of “proton sponges”.

IONOACTIVE IMINES - 1-R-BENZIMIDAZOL- 2-AMINE DERIVATIVES

Novel ionoactive imines possessing potent chromogenic and fluorogenic properties were accessed by condensation of 1-R-benzimidazol-2-amines with trans-5-[2-(anthracen-9-yl)vinyl]-2-hydroxybenz-aldehyde. These sensors exhibit ability for an intramolecular proton transfer in the excited state and could find use as selective analytical reagents for fluoride ions.

Imidazo[1,2-a]benzimidazole derivatives: XXIX. 1-allyl-2-amino-3-acylmethylbenzimidazolium halides and syntheses on their base

Cyclization of 1-allyl-2-amino-3-acylmethylbenzimidazolium halides under alkaline conditions gave 9-allyl-substituted imidazo[1,2-a]benzimidazoles. Cyclization of the same compounds on heating in concentrated hydrobromic acid was accompanied by addition of hydrogen bromide at the exocyclic double bond. Competing cyclizations with participation of the 1-(2-bromopropyl) and 3-acylmethyl substituents in 2-imino-2,3-dihydro-1H-benzimidazole were studied. Functionalization of the imidazo[1,2-a]benzimidazole system was performed via introduction of substituents into the 3-position and replacement of bromine in the 2-bromopropyl group in the 9-position.

Research in the field of imidazo[1,2-a]benzimidazole derivatives: XXVII. 1-acylmethyl-2-(ω-hydroxyalkylamino)-benzimidazoles and their transformation into derivatives of tricyclic systems

Abstract1-Acylmethyl-2-(ω-hydroxyalkylamino)benzimidazoles were synthesized and their behavior under various conditions was investigated: at the thermolysis without solvent, at heating in DMF or in 2-aminoethanol, hydrohalic acids, and acetic anhydride, in the presence of chlorinating agents (SOCl2, POCl3). Depending on the reaction conditions derivatives were obtained of 1H-imidazo[1,2-a]-benzimidazole, 9H-2,3-dihydroimidazo[1,2-a]benzimidazole, and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]-benzimidazole that were suitable synthons for the synthesis of functionally substituted derivatives of these tricyclic systems.

Fluorescent sensors based on 2-substituted imidazolidines

A number of 2-substituted imidazolidines were synthesized from N,N′-dibenzylethane-1,2-diamine derivatives and benzaldehyde, naphthalene-1-carbaldehyde, 2-hydroxynaphthalene-1-carbaldehyde, and anthracene-9-carbaldehyde. Examination of the obtained compounds by spectral methods revealed selective sensor properties of 2-(anthracen-9-yl)-1,3-dibenzylimidazolidine and 2-(anthracen-9-yl)-1,3-bis(2-hydroxybenzyl)-imidazolidine for Hg2+ and Cu2+ ions.