New Fluorescent Heterocyclic Compounds Derived From 3-Cyanobenzanthrone

3-(Phenylethynyl)-7H-benzo[de]anthracen-7-one

“…As far as we know, in the scope of palladium-catalyzed reactions, only aryl cyanation and Buchwald-Hartwig amination reactions have been used to obtain new benzanthrone derivatives [13,28], while the Sonogashira coupling, which is employed for the synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one (2) (Scheme 1), has not yet been utilized.…”

“…As far as we know, in the scope of palladium-catalyzed reactions, only aryl cyanation and Buchwald-Hartwig amination reactions have been used to obtain new benzanthrone derivatives [13,28], while the Sonogashira coupling, which is employed for the synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one (2) (Scheme 1), has not yet been utilized. The title compound 2 was synthesized under Sonogashira coupling reaction conditions using 10 mol % PdCl2 as the pre-catalyst with 20 mol % PPh3 as the liganting species and 10 mol % CuI as the co-catalyst in N,N-dimethylformamide (DMF) at 80 °C with triethylamine as a base [29].…”

“…Amongst anthraquinoid dyes, 7H-benzo[de]anthracen-7-one (benzanthrone) derivatives have gained wide recognition lately due to their excellent luminescent properties, such as photostability, sizable Stokes shifts, and noticeable solvatochromism, as well as their tunable fluorescence emission (from green to red) that is dependent on the nature of the substituents of the benzanthrone molecule and solvent properties [1][2][3] which enable these organic chromophores for use in a vast number of applications, both for scientific and technological needs. Namely, these compounds have reasonable potential to be used: as lipophilic fluorescent probes for parasitic trematodes and nematodes; for the diagnostics of several plant species' callus embryos by confocal laser scanning microscopy imaging [4][5][6][7]; for the selective detection of amyloid fibrils of the enzyme lysozyme [8,9]; as luminophore dyes in liquid crystal displays and polymeric materials [10][11][12]; for the production of organic thin films; and as probes for chromium(III) cations and the pH of solutions [13][14][15].…”

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

“…For anthraquinones, these include: serving as emitters in organic light-emitting diodes (OLEDs) [ 6 , 7 ], detecting ionic species in chemosensory processes [ 8 , 9 ], contributing to cellular imaging [ 10 , 11 ], and finding utility in the medical field as agents with fungicidal, antibacterial, insecticidal, antiparasitic, antiviral, and anticancer properties [ 12 ]. On the other hand, benzanthrones are suited for diverse uses: in liquid crystal displays [ 13 , 14 ], polymeric materials [ 15 ], as probes for the pH of solutions and cations [ 16 , 17 ], selective detectors of amyloid fibrils of the lysozyme enzyme [ 18 ], and visualization of parasitic trematodes and nematodes through confocal laser scanning microscopy imaging [ 19 ].…”

Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives

“…Moreover, these substances can be selectively deployed to identify amyloid fibrils [ 12 , 13 ]. Benzanthrone derivatives also have the potential to be utilized in liquid crystal displays [ 14 , 15 ], polymeric materials [ 16 , 17 ] and as probes to determine the pH levels and presence of cations in solutions [ 18 , 19 , 20 ]. These multiple benefits of these compounds have shown them to be a potential tool for various industries and research fields.…”