Cofacial Organic Click Cage to Intercalate Polycyclic Aromatic Hydrocarbons

The
synthesis of a 3-fold symmetric cofacial organic cage (COC)
through Cu­(I)-catalyzed azide–alkyne cycloaddition is reported.
The COC can function as an efficient receptor for carcinogenic polycyclic
aromatic hydrocarbons to intercalate them in its intrinsic cavity
through donor–acceptor and π···π
stacking interactions. The association constants (Ka) are in the range of 3.7 × 104 to 1.3
× 106 M–1. X-ray diffraction analysis
authenticated that the polycyclic aromatic hydrocarbons (PAHs) are
intercalated in the interior of the COC.

本研究报道了通过一价铜（Cu(I)）催化叠氮-炔环加成反应合成三重对称面型有机笼（COC）的工作。该有机笼可作为高效受体，通过供体-受体相互作用与π···π堆叠作用，将致癌性多环芳烃嵌入其内部空腔。其结合常数（Ka）介于3.7×10⁴ 至1.3×10⁶ M⁻¹范围内。经X射线衍射分析证实，多环芳烃（PAHs）成功嵌入该有机笼的内部空腔。