Halide anion mediated dimerization of a meso-unsubstituted N-confused porphyrin.
The new N-confused porphyrin (NCP) derivatives, meso-unsubstituted beta-alkyl-3-oxo N-confused porphyrin (3-oxo-NCP) and related macrocycles, were synthesized from appropriate pyrrolic precursors by a [3+1]-type condensation reaction. 3-Oxo-NCP forms a self-assembled dimer in dichloromethane that is stabilized by complementary hydrogen-bonding interactions arising from the peripheral amide-like moieties. The protonated form of 3-oxo-NCP was observed to bind halide anions (F(-), Cl(-)) through the outer NH and the inner pyrrolic NH groups, thus affording a dimer in dichloromethane. The structure of the chloride-bridged dimer in the solid state was determined by X-ray diffraction analysis.
Furuta
Hiroyuki
H
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395, Japan, Fax: (+81) 92-802-2865.|PRESTO, Japan Science and Technology Agency (JST), Kawaguchi 332-0012, Japan.
Nanami
Hideki
H
Department of Chemistry, Faculty of Sciences, Ehime University, Matsuyama 790-8577, Japan.
Morimoto
Tatsuki
T
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395, Japan, Fax: (+81) 92-802-2865.
Ogawa
Takuji
T
Department of Chemistry, Faculty of Sciences, Ehime University, Matsuyama 790-8577, Japan.|Research Center for Molecular-Scale Nanoscience, Institute for Molecular Science, Okazaki 444-8787, Japan.
Král
Vladimir
V
Department of Chemistry and Biochemistry, Institute of Cellular and Molecular Biology, The University of Texas at Austin, Austin, TX 78712-0165, USA, Fax: : (+1) 512-471-7550.
Sessler
Jonathan L
JL
Department of Chemistry and Biochemistry, Institute of Cellular and Molecular Biology, The University of Texas at Austin, Austin, TX 78712-0165, USA, Fax: : (+1) 512-471-7550.
Lynch
Vincent
V
Department of Chemistry and Biochemistry, Institute of Cellular and Molecular Biology, The University of Texas at Austin, Austin, TX 78712-0165, USA, Fax: : (+1) 512-471-7550.
D003461:Crystallography; D019281:Dimerization; D006219:Halogens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011166:Porphyrins / Q000737:chemistry*
D006219:Halogens; D011166:Porphyrins