Synthesis, DFT calculations and cyclic voltammetry analysis of new heterocyclic green dyes: 2-(5-Hydroxyimino-1-alkyl-4,5-dihydro-1H-4-indazolyliden)-2-arylacetonitriles

Pyrazolo[4,3-a]quinindoline as a new highly fluorescent heterocyclic system: Design, synthesis, spectroscopic characterization and DFT calculations

“…Taking this body of research into consideration and in continuation of our studies on the synthesis of nitrogen heterocyclic compounds, specially new dyes and fluorescent heterocyclic compounds [28][29][30][31][32][33][34][35], in current work, we decided to design and synthesis of a new heterocyclic system pyrazolo [4,3-a]quinindoline via the nucleophilic substitution of hydrogen [36] of 1-alkyl-5-nitro-1H-indazole with 2-(1-alkyl-1H-3-indolyl)acetonitrile in basic media. Spectroscopic characterization, fluorescence properties, DFT and TD-DFT calculations of these dyes were also studied.…”

“…The work-up procedure was very simple which was performed by filtration of the precipitated product after the mixture was concentrated at reduced pressure. Washing the precipitated product with suitable solvents (water and then acetone) gives practically pure compounds 3a-d. R= Me, R'= Me (73%) 3b: R= Me, R'= Et (75%) 3c: R= Et, R'= Me (70%) 3d: R= Et, R'= Et (80%) Synthesis of new compounds 3a-d.In the following mechanism[29][30][31][32][33][34][35] the ring closure proceeding occurs via an electrocyclic pathway, wherein intermediate B is converted to C followed by losing one H Proposed reaction mechanism for the formation of compounds 3a-d.The structure of target products 3a-d was confirmed by NMR techniques, FT-IR spectroscopy, mass spectral and microanalytical data. The spectral details of all these are given in experimental section.…”

Synthesis, DFT calculations, cyclic voltammetry and antibacterial activities of a new blue-violet dye and a new blue-green fluorescent heterocyclic system

“…The physicochemical properties of these compounds have relevance in the design of new materials, especially organic conductors. 8 Taking this body of research into consideration and in continuation of our studies on the synthesis of new solvent dyes and nitrogen and sulfur-nitrogen fluorescent heterocyclic compounds, [9][10][11][12][13][14] we have synthesized a new blue-violet dye, 2-(3-hydroxyimino-2,3-dihydroimidazo[1,2-a]pyridin-2-yliden)-2-(2-thienyl)acetonitrile, via nucleophilic substitution of hydrogen, 15 and a new blue-green sulfur-nitrogen fluorescent heterocyclic system, pyrido[2 0 ,1 0 :2, 3]imidazo [4,5-b]thieno[2,3-e]pyridine-11-carbonitrile, in excellent yields. DFT calculations and cyclic voltammetry analysis were performed and the antibacterial activities of these dyes were also studied.…”

Synthesis, spectroscopic characterization and DFT calculations of a new highly fluorescent heterocyclic system: imidazo[4,5-a]quinindoline

“…In the following mechanism [17][18][19][20][21][22][23] the ring closure proceeds via an electrocyclic pathway, wherein intermediate B is converted into C followed by loss of one H 2 O molecule, whereupon compounds 3a-d are obtained (Scheme 2).…”

“…Based on these aspects and in continuation with our research work on the efficient synthesis of new dyes and fluorescent nitrogen heterocyclic compounds, [17][18][19][20][21][22][23] we examined the transformation of 1-alkyl-5-nitro-1H-benzoimidazole with 2-(1-alkyl-1H-3-indolyl)acetonitrile to new fluorescent heterocyclic system imidazo [4,5-a]quinindoline via the nucleophilic substitution of hydrogen. 24,25 The fluorescence properties of these new heterocyclic compounds and DFT calculations of one structure by using the B3LYP hybrid functional and the 6-311+G(d,p) basis set have also been studied.…”