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

Abstract

In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a nitro group in comparison with 3-bromobenzanthrone. The new compounds exhibit intense absorption and pronounced luminescent properties in various organic solvents. In this regard, their photophysical properties were evaluated with an experimental study of the solvatochromic behavior of the obtained compounds in various solvents. It has recently been found that the addition of an electron-withdrawing nitro group to the benzanthrone core increases its first- and second-order hyperpolarizability. Such dyes can be used in the fabrication of optical limiter devices. Therefore, the developed fluorescent molecules have a potential prospect for extensive application in optoelectronics.

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

“…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 ]. This suggests that the benzanthrone amino group, when attached to a phosphoryl group, demonstrates a stronger donating effect compared to amidino and thiol groups, albeit to a slightly lesser degree than an alkyl amino group.…”