Benzanthrone sulfides: synthesis, solvatochromism characterization and analysis of experimental photophysical parameters and theoretical calculations

Maļeckis, Armands; Cvetinska, Marija; Griškjāns, Evans; Dmitrijevs, Kirills; Traskovskis, Kaspars; Belyakov, Sergey; Kirilova, Elena

doi:10.1016/j.dyepig.2023.111599

Cited by 2 publications

(1 citation statement)

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“…The introduction of strong electron-accepting groups ( 2c and 4c ) significantly decreased both the extinction coefficients and quantum yields. The absorption spectra of the recently examined benzanthrone alkyl and aryl sulfides spanned from 403 to 448 nm [ 44 ], and amidines absorbed in the range of 410 to 495 nm [ 45 , 46 ], whereas 3-substituted benzanthrone amino derivatives exhibited absorption between 430 and 520 nm [ 47 ]. For 3-amino-9-nitrobenzanthrone derivatives, absorption occurred in the range of 450 to 560 nm [ 48 ].…”

Section: Resultsmentioning

confidence: 99%

A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of Opisthorchis felineus

Maļeckis,

Cvetinska,

Kirjušina

et al. 2024

Molecules

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In this research, we explore the synthesis of and characterize α-aminophosphonates derived from anthraquinone and benzanthrone, focusing on their fluorescence properties and potential applications in confocal laser scanning microscopy (CLSM). The synthesized compounds exhibit notable solvatochromic behavior, emitting fluorescence from green to red across various solvents. Spectroscopic analysis, including 1H-, 13C-, and 31P-NMR, FTIR, and mass spectrometry, confirms the chemical structures. The compounds’ toxicity is evaluated using etiolated wheat sprouts, revealing varying degrees of impact on growth and oxidative damage. Furthermore, the study introduces these α-aminophosphonates for CLSM imaging of the parasitic flatworm Opisthorchis felineus, demonstrating their potential in visualizing biological specimens. Additionally, an X-ray crystallographic study of an anthraquinone α-aminophosphonate provides valuable structural insights.

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