3 years ago

Conjunction of Pyrrole and Amide Moieties: Highly Anion-Responsive π-Electronic Molecules Forming Ion-Free and Ion-Pairing Assemblies

Conjunction of Pyrrole and Amide Moieties: Highly Anion-Responsive π-Electronic Molecules Forming Ion-Free and Ion-Pairing Assemblies
Atsuko Kuno, Nobuhiro Yasuda, Hiromitsu Maeda, Norimitsu Tohnai
Dipyrrolyldiketone BF2 complexes with amide units at pyrrole α-positions were synthesized in modest yields and showed extremely high anion-binding affinities because of multiple hydrogen-bonding interactions. The phenyl-amide-substituted derivative formed solid-state chiral helical structures, wherein π planes were oriented parallel to the helical directions. Examination of anion-binding behavior using 1H NMR spectroscopy combined with theoretical studies suggested fast pyrrole inversions, particularly for the phenyl-amide-substituted derivative. The anion complexes behaved as building units of ion-pairing assemblies in combination with planar and bulky cations. A good reception: Dipyrrolyldiketone BF2 complexes with amide units at pyrrole α-positions were synthesized and showed extremely high anion-binding affinities through multiple hydrogen bonding (see figure). Anion-binding behavior examined by 1H NMR spectroscopy along with theoretical studies suggested rapid pyrrole inversions in solution state. In the solid state, chiral helical structures of an anion-free receptor and ion-pairing assemblies of anion complexes were formed through hydrogen bonding.

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

DOI: 10.1002/chem.201701921

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