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π–π interaction of quinacridone derivatives
Author(s) -
Huang Zhaowei,
Sun Hui,
Zhang Houyu,
Wang Yue,
Li Fei
Publication year - 2011
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.21782
Subject(s) - antiparallel (mathematics) , stacking , chemistry , substituent , density functional theory , intermolecular force , computational chemistry , interaction energy , aromaticity , crystallography , stereochemistry , molecule , physics , organic chemistry , quantum mechanics , magnetic field
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. © 2011 Wiley Periodicals, Inc. J Comput Chem, 2011