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Synthesis, Structure, and Spectroscopy of Phenylacetylenylene Rods Incorporating meso ‐Substituted Dipyrrin Ligands
Author(s) -
Halper Sara R.,
Cohen Seth M.
Publication year - 2003
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.200305041
Subject(s) - chemistry , moiety , supramolecular chemistry , molecule , crystallography , fluorescence , stereochemistry , crystal structure , organic chemistry , physics , quantum mechanics
The synthesis, structure, and spectroscopic characterization of a series of phenylacetylenylene rodlike molecules containing dipyrromethene (dipyrrin) ligands are described. The combination of the phenylacetylenylene groups with the porphyrinogenic dipyrrin moieties results in a rich absorption spectroscopy for these compounds, although the fluorescence of the phenylacetylenylene moiety is quenched by presence of the dipyrrin chelator. The Cu 2+ and Fe 3+ complexes of these ligands have been prepared and three of these compounds have been structurally characterized by using single‐crystal X‐ray diffraction. Unlike other octahedral metal‐dipyrrin complexes described to date, one of the iron complexes demonstrates ideal threefold symmetry in the solid‐state. The elongated structure and high symmetry of these complexes suggests the use of these meso ‐substituted phenylacetylenylene ligands as an interesting class of extended, branched molecules for the construction of supramolecular architectures.