期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 6, 页码 2572-2580出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00209
关键词
-
资金
- ETH Zurich, Switzerland [ETH-26 10-2]
The novel hydrocarbon propeller-shaped D-3h-symmetric cydophane (3), anthraphane, was prepared through a revisited and optimized gram-scale synthesis of the key building block anthracene-1,8-ditriflate 7. Anthraphane has a high tendency to crystallize and single crystals in size ranges of 100-200 mu mare easily obtained from different solvents. The crystallization behavior of 3 was extensively studied to unravel packing motifs and determine whether the packing can be steered into a desired direction, so to allow topochemical photopolymerization. SC-XRD shows that anthraphane packs in layers irrespective of the solvent used for crystallization. However, within the layers, intermolecular arrangements and pi-pi interactions of the anthracene units vary strongly. Four interaction motifs for the anthracene moieties are observed and discussed in detail: two types of exclusively edge-to-face (etf), a mixture of edge-to-face and face-to-face (ftf), and no anthracene anthracene interaction at all. To elucidate why an exclusive ftf stacking was not observed, electrostatic potential surface (EPS) calculations with the semiempirical PM3 method were performed. They show qualitatively that the anthracene faces bear a strong negative surface potential, which may be the cause for this cydophane to avoid ftf interactions. This combined crystallographic and computational study provides valuable insights on how to create all-ftf packings.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据