π–π interaction of quinacridone derivatives

Abstract

The π–π stacking interactions play an important role in molecular assemblies of quinacridone derivatives (QAs). In our previous work (Sun et al., J Phys Chem A 2008, 112, 11382), we have shown that quinacridone derivatives can be self-associated as dimers in solution by means of NMR study. Herein, we perform theoretical studies on the molecular interaction in the dimers of QAs to illustrate π–π interactions in terms of their strength, geometrical preference, substituent effect, and physical nature. Density functional theory (DFT-D) was adopted to calculate potential energy surfaces. The detailed analysis on the intermolecular interaction in diversity of dimeric configurations reveals that the displaced conformations with specific geometries in both parallel and antiparallel stacking manners can be stabilized, which are in agreement with NMR experimental findings.

How the substituents in corannulene and sumanene derivatives alter their molecular assemblings and charge transport properties?-A theoretical study with a dimer model

“…On the contrary, the S‐series dimers nearly possess the same rotation angle ( θ = 60°), except S‐2CF3 dimer ( θ = 130°), though the vertical separation is different. As for the C‐series, it is interesting to find that the C dimer with the strongest binding interaction energy shows the optimal configuration of perfect eclipsed ( θ = 0°) molecular stacking, which generally makes the dimer less stable due to a strong electronic repulsion, especially for planar dimers . Furthermore, the optimal configuration of the C‐2CF3 dimer predicted by the calculation is in agreement with the experiment result .…”

Attenuation of Cytotoxic Natural Product DNA Intercalating Agents by Caffeine

“…Interactions that likely contribute to these favorable π–π complexes include dipole-dipole interactions [33, 34], electrostatic interactions [35, 36] and van der Waals interactions [37], as well as frontier molecular orbital interactions [38, 39]. Frontier molecular orbital theory [40] suggests that the important interactions of caffeine with the intercalating drugs will be the HOMO of caffeine and the LUMO of the antitumor agents.…”

Two new copper and nickel complexes of pyridine-2,6-dicarboxylic acid N-oxide and their proton transferred salts: Solid state and DFT insights

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