Two novel D-A-π-A1 metal-free organic dyes of the series containing benzo[][1,2,3]thiadiazole (isoBT) internal acceptor, indoline donors fused with cyclopentane or cyclohexane rings (D), a thiophene as a π-spacer, and a cyanoacrylate as an anchor part were synthesized. Monoarylation of 4,7-dibromobenzo[][1,2,3]thiadiazole by Suzuki-Miyamura cross-coupling reaction showed that in the case of indoline and carbazole donors, the reaction was non-selective, i.e.
View Article and Find Full Text PDFThis article presents the results of a study of electrochemical transformations in aqueous and aprotic media of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide l-arginine monohydrate (, Triazid) obtained by electrochemical methods and ESR spectroscopy. The effect of pH on the current and the reduction potential of in an aqueous Britton-Robinson buffer solution was studied. It was found that 1a is irreversibly reduced in aqueous acidic media on a glassy carbon electrode in one stage with the participation of six electrons and the formation of 5-methyl-6-amino-7-oxo-1,2,4-triazolo[1,5-a]pyrimidin.
View Article and Find Full Text PDFThis paper presents an improved synthesis of 4,7-dibromobenzo[][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[][1,2,3]thiadiazole (isoBTD) has higher values of E and energy band gap (E), which indicates high electron conductivity, occurring due to the high stability of the molecule in the excited state. We studied the cross-coupling reactions of this dibromide and found that the highest yields of π-spacer-acceptor-π-spacer type compounds were obtained by means of the Stille reaction.
View Article and Find Full Text PDFThe possibility of using a single light-emitting layer consisting of newly synthesized fluorescent small organic molecules of D-A-π-A type incorporated into a conductive matrix together with an electron conductive Alq layer in order to form radiation in candle light-style OLEDs was shown for the first time. A record low color temperature of 1722 K OLED radiation was achieved, which is by 80 K lower than that of the best devices reported previously.
View Article and Find Full Text PDFFour new D-A-π-A metal-free organic sensitizers for dye-sensitized solar cells (DSSCs), with [1,2,5]thiadiazolo[3 ,4-]pyridazine as internal acceptor, thiophene unit as π-spacer and cyanoacrylate as anchoring electron acceptor, have been synthesized. The donor moiety was introduced into [1,2,5]thiadiazolo[3,4-]pyridazine by nucleophilic aromatic substitution and Suzuki cross-coupling reactions, allowing design of D-A-π-A sensitizers with the donor attached to the internal heterocyclic acceptor not only by the carbon atom, as it is in a majority of DSSCs, but by the nitrogen atom also. Although low values of power conversion efficiency (PCE) were found, a few important consequences were identified: (i) poor PCE data can be attributed to high electron deficiency of the internal [1,2,5]thiadiazolo[3,4-]pyridazine acceptor due to lower light harvesting by the dye; (ii) the manner in which the donor was attached to the internal acceptor (by carbon or nitrogen) did not play an essential role in the photovoltaic properties of the dyes; (iii) dyes based on the novel donor 2,3,4,4a,9,9a-hexahydro-1-1,4-methanocarbazolyl and 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H- carbazole moieties showed similar photovoltaic properties to dyes based on the well-known 4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indolyl building block, which opens the door for further optimization potential of new dye families.
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