Fluorescent substituted amidines of benzanthrone: Synthesis, spectroscopy and quantum chemical calculations

Gonta, Svetlana; Utinans, M.; Kirilov, G; Belyakov, Sergey; Ivanova, I. F.; Fleisher, M.; Savenkov, Valerij; Kirilova, Elena

doi:10.1016/j.saa.2012.09.104

Cited by 36 publications

(27 citation statements)

References 21 publications

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“…The classical donor–acceptor dyes with a strong solvatochromism and an improved Stokes shift include coumarins and squaraines . Benzanthrones with electron‐withdrawing groups at 3‐position also belong to such luminophores with ICT …”

Section: Resultsmentioning

confidence: 99%

Novel dye for detection of callus embryo by confocal laser scanning fluorescence microscopy

et al. 2019

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In the present study a new luminescent dye 3‐N‐(2‐pyrrolidinylacetamido)benzanthrone (AZR) was synthesized. Spectroscopic measurements of the novel benzanthrone 3‐aminoderivative were performed in seven organic solvents showing strong fluorescence. The capability of the prepared dye for visualization has been tested on flax, red clover and alfalfa to determinate the embryo in plant callus tissue cultures. Callus cells were stained with AZR and further analysed utilizing confocal laser scanning fluorescence microscopy. Performed experiments show high visualization effectiveness of newly synthesized fluorescent dye AZR that is efficient in fast and relatively inexpensive diagnostics of callus embryos that are problematic due to in vitro culture specificity.

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Section: Resultsmentioning

confidence: 99%

Novel dye for detection of callus embryo by confocal laser scanning fluorescence microscopy

et al. 2019

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“…The dye 3‐MAB was synthesized as described in the scheme of a previous article . The solvents 1,4‐dioxane, benzene, toluene, ethyl acetate, THF, DCM, 2‐propanol, acetone, ethanol, methanol, acetonitrile, dimethylformamide, and dimethylsulphoxide were of spectroscopic grade and were procured from S‐D Fine Chemicals Ltd (Mumbai, India).…”

Section: Methodsmentioning

confidence: 99%

Solvatochromic study of 3‐N‐(N′‐methylacetamidino)benzanthrone and its interaction with dopamine by the fluorescence quenching mechanism

Bharathi¹,

Siddlingeshwar²,

Shivraj³

et al. 2018

Luminescence

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The change in photophysical properties of the organic molecule due to solvatochromic effect caused by different solvent environments at room temperature gives information about the dipole moments of 3-N-(N'-methylacetamidino)benzanthrone (3-MAB). The quantum yield, fluorescence lifetime of 3-MAB was measured in different solvents to calculate radiative and non-radiative rate constants. The results revealed that the excited state dipole moment (μ ) is relatively larger compared to the ground state dipole moment (μ ), indicating the excited state of the dye under study is more polar than the ground state and the same trend is noticed with theoretical calculations performed using the CAM-B3LYP/6-311+G(d,p) method. Further, the study on preferential solvation was carried out for 3-MAB dye in ethyl acetate-methanol solvent mixture. The fluorescence quenching method has been employed for the detection of dopamine using 3-MAB as fluorescent probe, using steady-state and time resolved methods at room temperature. The method enables dopamine in the micro molar range to be detected. Also, an attempt to verify the quenching process by employing different models has been tried. Various rate parameters are measured using these models, our results indicates the quenching process is diffusion limited.

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“…The substances 8 and 9 have low solubility in water and aggregates of the molecules are expected in dioxane/watermixtures, so at these mixtures the solid-state luminescence is probably observed. The similar approach was presented in the works[41,42] to observe solid-state luminescence of diazabenzopyrenes and benzanthrones in solutions. The solid-state origin of luminescence of 8b and 9b in dioxane/water solutions was confirmed by the luminescence lifetimes of 8b and 9b which were obtained very similar for the solid states and the dioxane/water mixtures at high water concentrations(Fig.…”

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confidence: 92%

Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties

et al. 2017

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Fluorescent substituted amidines of benzanthrone: Synthesis, spectroscopy and quantum chemical calculations

Cited by 36 publications

References 21 publications

Novel dye for detection of callus embryo by confocal laser scanning fluorescence microscopy

Novel dye for detection of callus embryo by confocal laser scanning fluorescence microscopy

Solvatochromic study of 3‐N‐(N′‐methylacetamidino)benzanthrone and its interaction with dopamine by the fluorescence quenching mechanism

Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties

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