Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Construction of π-Surface-Metalated Pillar[5]arenes which Bind Anions via Anion–π Interactions

Construction of π-Surface-Metalated Pillar[5]arenes which Bind Anions via Anion–π Interactions
Hai-Bo Yang, Ying Zhang, Wei Wang, Xiaopeng Li, Hongwei Tan, Guang-Qiang Yin, Ye Lu, Chang-Wei Zhang, Bo Jiang, Xiao-Li Zhao, Guo-Xin Jin, Lin Xu
By simple ligand exchange of the cationic transition-metal complexes [(Cp*)M(acetone)3](OTf)2 (Cp*=pentamethylcyclopentadienyl and M=Ir or Rh) with pillar[5]arene, mono- and polynuclear pillar[5]arenes, a new class of metalated host molecules, is prepared. Single-crystal X-ray analysis shows that the charged transition-metal cations are directly bound to the outer π-surface of aromatic rings of pillar[5]arene. One of the triflate anions is deeply embedded within the cavity of the trinuclear pillar[5]arenes, which is different to the host–guest behavior of most pillar[5]arenes. DFT calculation of the electrostatic potential revealed that the metalated pillar[5]arenes featured an electron-deficient cavity due to the presence of the electron-withdrawing transition metals, thus allowing encapsulation of electron-rich guests mainly driven by anion–π interactions. Cavity filling: A simple yet highly efficient approach gives pillar[5]arene hosts with metalated π-surfaces. The metalated pillar[5]arenes have an electron-deficient cavity owing to the presence of the electron-withdrawing transition-metal moieties, thus allowing the encapsulation of anion guests via anion–π interactions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707209

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