Optical Absorption and Emission Properties of Fluoranthene, Benzo[k]fluoranthene, and Their Derivatives. A DFT Study

Abstract

Fluoranthene and benzo[k]fluoranthene-based oligoarenes are good candidates for organic light-emitting diodes (OLEDs). In this work, the electronic structure and optical properties of fluoranthene, benzo[k]fluoranthene, and their derivatives have been studied using quantum chemical methods. The ground-state structures were optimized using the density functional theory (DFT) methods. The lowest singlet excited state was optimized using time-dependent density functional theory (TD-B3LYP) and configuration interaction singles (CIS) methods. On the basis of ground- and excited-state geometries, the absorption and emission spectra have been calculated using the TD-DFT method with a variety of exchange-correlation functionals. All the calculations were carried out in chloroform medium. The results show that the absorption and emission spectra calculated using the B3LYP functional is in good agreement with the available experimental results. Unlikely, the meta hybrid functionals such as M06HF and M062X underestimate the absorption and emission spectra of all the studied molecules. The calculated absorption and emission wavelength are more or less basis set independent. It has been observed that the substitution of an aromatic ring significantly alters the absorption and emission spectra.

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

“…The hybrid functionals namely B3LYP (Becke3-Lee-YangParr hybrid functional) [40][41][42][43] was used. The 6-31G(d) basis set was used for all atoms and later was ascertained in the literature [44]. The Polarizable Continuum Model (PCM) [45] was used to optimize the ground and excited state geometries.…”

Biotransformation of the high‐molecular weight polycyclic aromatic hydrocarbon (PAH) benzo[k]fluoranthene by Sphingobium sp. strain KK22 and identification of new products of non‐alternant PAH biodegradation by liquid chromatography electrospray ionization tandem mass spectrometry

“…Structurally, benzo[k]fluoranthene may be viewed as a single-or double-benzannelated derivative of the four-ring and three-ring PAHs fluoranthene and acenaphthylene respectively. These three molecules constitute a series of non-alternant PAHs whereby the combination of five-and six-membered rings that comprise their structures is also the structural motif upon which many new materials that are under development are based, including organic light-emitting diodes, fullerenes and in the termination of single-wall carbon nanotubes (Birer et al, 2007;Xia et al, 2010;Saranya et al, 2011). As a member of the five-ring HMW PAH class, benzo [k]fluoranthene is considered to be more resistant to biotransformation partly due to its molecular stability, hydrophobicity and low water solubility, which is approximately 1 ug L −1 or less (Cerniglia, 1992;De Maagd et al, 1998;Sverdrup et al, 2002).…”

Electronic structure and spectroscopic properties of 6‐aminophenanthridine and its derivatives: Insights from density functional theory

“…Thus, our results indicate that the order of predicting power of absorption energy using these functionals is: B3LYP > PBE0 > M062X > M06HF (Supporting Information Table S1). Similar results were also reported in previous studies …”

“…Similar results were also reported in previous studies. [23] As far as the basis sets are concerned, we have compared the results of four different basis sets (6-31G*, 6-311G**, 6-311G*, 6-3111G**) (Supporting Information Table S1). Here, we restrict our discussion only for B3LYP functional as the other functionals show essentially the same trend.…”