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Conjunction of Pyrrole and Amide Moieties: Highly Anion‐Responsive π‐Electronic Molecules Forming Ion‐Free and Ion‐Pairing Assemblies
Author(s) -
Kuno Atsuko,
Tohnai Norimitsu,
Yasuda Nobuhiro,
Maeda Hiromitsu
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701921
Subject(s) - amide , ion , chemistry , pyrrole , molecule , hydrogen bond , affinities , derivative (finance) , crystallography , pairing , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , physics , superconductivity , quantum mechanics , financial economics , economics
Dipyrrolyldiketone BF 2 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 1 H 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.