Finding New Precursors for Light Harvesting Materials: A Computational Study of the Fluorescence Potential of Benzanthrone Dyes

Abstract

Benzanthrone dyes are organic luminophores with excellent optoelectronic properties. This computational investigation is based on density functional theory and aims to explore the photophysical behavior of some of the reported aminobenzanthrones in addition to many unreported dyes containing different electron-donating substituents. Significant changes in the dipole moment and the overall structure of the dyes upon solvation in ethanol have been observed. We find that intramolecular charge transfer is more pronounced in the solvent medium, which facilitates the emission to shift bathochromically. Intersystem crossing is predicted to be absent, which makes relaxation of the molecule to ground state more efficient by emitting in the visible region.

Green synthesis of novel spiropyrazoline-indolinones in neutral deep eutectic solvents and DFT studies

“…The non-bonding effects in the molecules were added using Grimme’s empirical dispersion correction [ [42] , [43] , [44] ] as implemented in Gaussian 09. The said method has been benchmarked earlier by us on a variety of similar studies and others as well and it proved to produce good results [ [45] , [46] , [47] , [48] , [49] , [50] , [51] ]. Solvent effects were added through the Polarizable Continuum Model (PCM) [ [52] , [53] , [54] , [55] , [56] , [57] , [58] ] added through Truhlar’s SMD parameter [ 59 ].…”

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

“…For comparison, a pair of derivatives with a piperidine residue containing a nitro group (5) and a previously synthesized non-nitrated derivative (6) were analyzed. In the example of benzanthrone derivative 5, as indicated by 1 H and COSY NMR spectra, signals of H-C(1) and H-C(2) appear as doublets at 8.27 and 7.12 ppm, respectively, with a coupling constant of 8 Hz.…”

“…In the anthrone family of fluorescent dyes, a four-cyclic condensed aromatic ketone, benzanthrone, has been confirmed to display the excellent above-mentioned characteristics, which prompts the synthesis of new derivatives and their study [ 6 , 7 ]. Previously, benzanthrone compounds have found utilization as fluorescent bioimaging probes, which can aid in the visualization of parasitic trematodes and nematodes [ 8 , 9 , 10 ], as well as in the identification of callus embryos of different plant species through the use of confocal laser scanning microscopy imaging [ 11 ].…”

“…Over the last few decades, 3-aminobenzanthrone derivatives (including alkylamines and imines [ 6 , 15 , 24 ], amides [ 25 , 26 , 27 ], amidines [ 28 ] and aminophosphonates [ 29 ]) have become the subject of significant attention. Among these many derivatives, substituted 3-piperazinyl derivatives of benzanthrone [ 30 , 31 ], as well as 3-(4-(diphenylamino)phenyl)benzanthrone and perylenediimide–benzanthrone dyads, were recently found to exhibit nonlinear optical (NLO) properties [ 32 , 33 ], which propels their design and use not only for imaging and sensing but also for applications in laser technology and optical communications.…”

N′-(3-Bromo-7-oxo-7H-benzo[de]anthracen-9-yl)-N,N-dimethylimidoformamide

“…Among benzanthrone monoamines, the greatest interest has been attracted by 3-, 4-, 6-and 8-amino derivatives as precursors for dyes with interesting optoelectronic properties [6][7][8][9]. In contrast to the widely studied various monoamine derivatives of benzanthrone, disubstituted benzanthrone derivatives have been insufficiently studied.…”