Huang Zhaowei, Sun Hui, Zhang Houyu, Wang Yue, Li Fei
State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, People's Republic of China.
J Comput Chem. 2011 Jul 30;32(10):2055-63. doi: 10.1002/jcc.21782. Epub 2011 May 3.
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.
π-π堆积相互作用在喹吖啶酮衍生物（QAs）的分子组装中起着重要作用。在我们之前的工作中（Sun等人，《物理化学杂志A》2008年，112卷，11382页），通过核磁共振研究表明喹吖啶酮衍生物在溶液中可以自缔合形成二聚体。在此，我们对QA二聚体中的分子相互作用进行理论研究，以从其强度、几何偏好、取代基效应和物理性质方面阐明π-π相互作用。采用密度泛函理论（DFT-D）计算势能面。对多种二聚体构型中分子间相互作用的详细分析表明，以平行和反平行堆积方式具有特定几何形状的错位构象可以得到稳定，这与核磁共振实验结果一致。
