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Publikācija: Synthesis and Properties of Substituted p-Phenylenediamine Donor and 1H-indene-1

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Nosaukums oriģinālvalodā Synthesis and Properties of Substituted p-Phenylenediamine Donor and 1H-indene-1,3(2H)-dione Acceptor-Based Chromophores
Pētniecības nozare 1. Dabaszinātnes
Pētniecības apakšnozare 1.4. Ķīmija
Autori Jekaterina Boļšakova
Lauma Laipniece
Kristīne Lazdoviča
Baiba Turovska
Valdis Kampars
Atslēgas vārdi chromophores, triphenylamine
Anotācija In order to evaluate the influence of insertion of the strong electron-donating groups on the p-position of triphenylamine unit upon physical properties novel chromophores containing N,N-dibutyl- or N,N-diphenylsubstituted triphenylamine donor and 1H-indan-1,3(2H)-dionе acceptor have been synthesized via Knoevenagel condensation reaction of 4-((4-dibutylamino)phenyl) (phenyl)amino)benzaldehyde, 4,4’-(4-(dibutylamino) phenylazanediyl)dibenzaldehyde and 4,4’-(4-diphenylamino) phenylazanediyl) dibenzaldehyde with 1H-indan-1,3(2H)-dionе. Vilsmeier-Haack formylation reaction of 4-bromo-N,N-diphenylbenzenamine and N1,N1-dibutyl-N4,N4-diphenylbenzene-1,4-diamine has been examined. It is shown that direct twofold Vilsmeier-Haack formylation of N1,N1-dibutyl-N4,N4-diphenylbenzene-1,4-diamine to get 4,4’-(4-(dibutylamino) phenylazanediyl)dibenzaldehyde with satisfactory yield is not possible but it could be obtained from 4,4’-(4-bromphenylazanediyl)dibenzaldehyde in a two-step process: first, protection of carbonyl groups, then Pd catalyzed amination followed by deprotection. 4,4’-(4-Diphenylamino) phenylazanediyl)dibenzaldehyde has been obtained in double N-arylation of N1,N1-diphenylbenzene-1,4-diamine with 2-(4-bromophenyl)-4-methyl-1,3-dioxolane under palladium(0) catalysis. All obtained chromophores have good solubility in common organic solvents. Thermal properties are little influenced by insertion of diphenylamino substituent, but substantially by dibutylamino substituent in the parent structure. Negative solvatochromism and slight bathochromic shift of charge transfer band of novel chromophores compared with unsubstituted triphenylamine core containing chromophores are observed in UV-Vis spectra. Chromophores containing two tertiary amine moieties in the molecule undergo irreversible anodic oxidation, and influence of substituents on the oxidation potentials has been studied. Nitrogen N-4 is shown as the primary reaction centre in the anodic oxidation. The cathodic reduction of the studied compounds proceeds close to -1 V. The reduction potentials of the electron acceptor 1H-indene-1,3(2H)-dione moieties are less sensitive to the substituent effects in the molecules.
Atsauce Sirotkina, J., Laipniece, L., Lazdoviča, K., Turovska, B., Kampars, V. Synthesis and Properties of Substituted p-Phenylenediamine Donor and 1H-indene-1,3(2H)-dione Acceptor-Based Chromophores. Materiālzinātne un lietišķā ķīmija . Nr.25, 2012, 57.-65.lpp. ISSN 1407-7353. e-ISSN 2255-8713.
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