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Ion‐Pairing Assemblies of π‐Electronic Anions Formed by Intramolecular Hydrogen Bonding
Author(s) -
Maeda Hiromitsu,
Takeda Yuka,
Haketa Yohei,
Morimoto Yuta,
Yasuda Nobuhiro
Publication year - 2018
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.201801375
Subject(s) - deprotonation , hydrogen bond , moiety , chemistry , intramolecular force , pairing , crystallography , ion , stacking , photochemistry , molecule , stereochemistry , organic chemistry , physics , superconductivity , quantum mechanics
π‐Extended nitro‐substituted dipyrrolylphenol derivatives were synthesized, and upon deprotonation they provided π‐electronic anions stabilized by hydrogen bonding between the phenolate (phenoxide) moiety and the pyrrole NH group. Ion‐pairing assemblies of the deprotonated anions were formed in the solid state and as mesophases. In the solid state, the extended π plane was found to be more suitable to form charge‐by‐charge assemblies in combination with tetraalkylammonium cations with highly anisotropic orientations as a result of efficient stacking. The mesophase also included a charge‐by‐charge assembly comprising the deprotonated anion bearing aliphatic chains, as revealed by synchrotron X‐ray diffraction analysis.