Luminescence and structural properties of thermally evaporated benzanthrone dyes thin films

Abstract

We report optical and luminescence properties of 3-N, N-diacetylaminobenzanthrone thin films deposited on glass substrate by thermal evaporation. The structural and optical properties of organic thin films were studied by means of the confocal microscope with an input of femtosecond laser radiation, X-ray diffractometer, and scanning electron microscope (SEM). Intense luminescence with the maximum at 530 nm was observed when excited by laser radiation with the wavelengths 458, 476, 488, 496, 514 nm. In addition, the luminescence caused by two-photon absorption of femtosecond (fs) laser radiation has been investigated. Semi empirical calculations by AM1 and ZINDO/S methods and ab initio calculations using Gaussian software were carried out to estimate the electron system of structure. The calculations show planar configurations for the aromatic core and diacetylamino fragment of this compound. The study of the structure of benzanthrone derivative thin films with X-ray diffraction (XRD) methods, indicates the distance between molecular layers and ordered molecular fragments.

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

“…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].…”

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

“…Benzanthrone (Scheme ) dyes are organic luminescent materials that have emission spectra anywhere from the green to the red spectral region . They are well known for having extended π-conjugation that endowed these compounds with interesting photophysical and photochemical characteristics − and excellent luminescence , and, more precisely, fluorescence − properties.…”

Computational Chemistry of Compounds with Donor-Acceptor Interactions

“…142 Intramolecular donor-acceptor interactions have long been known to exist in molecules with fluorescence characteristics. 9 Moreover, extended π conjugation such as the one present in dyes inserts photophysical and photochemical properties [143][144][145] which are subsequently responsible for the luminescence 146,147 and fluorescence [148][149][150] characteristics of these compounds. The recent increased interest in the synthesis of 3-aminobenzanthrone dyes is attributed to the fact that they are potential candidates in manufacturing liquid-crystalline material and opto-electronic devices.…”