jo401825k_si_002.cif (57.53 kB)
Stereochemistry and Solid-State Structure of an Intrinsically Chiral Meso-Patterned Porphyrin: Case Study by NMR and Single-Crystal X‑ray Diffraction Analysis
dataset
posted on 2013-10-04, 00:00 authored by Liguo Yang, Yang Zhou, Mengliang Zhu, Luyang Zhao, Liye Wei, Yongzhong BianA C1-symmerical meso-substituted
ABCD-type porphyrin, [5-phenyl-10-(2-hydroxynaphthyl)-15-(4-hydroxyphenyl)porphyrinato]zinc(II)
(1), has been synthesized and characterized. The molecular
structure of 1 has been determined by single-crystal
X-ray diffraction analysis. The complex 1 crystallizes
in a triclinic system with one pair of enantiomeric molecules per
unit cell. Resolution of the racemic mixture has been achieved by
chiral HPLC techniques. In particular, the absolute configurations
of the enantiomers have been assigned from NMR spectroscopic analysis
with l-Phe-OMe as the chiral solvating agent (CSA). The assignments
have also been unambiguously confirmed by single-crystal X-ray diffraction
analysis. The present results suggest that the CSA–NMR anisotropy
strategy is applicable for the stereochemistry determination of chiral
host–guest complexes with multiple intermolecular interactions.
In addition, the multiple intermolecular interactions between the
enantiomerically pure porphyrin S-1 and l-Phe-OMe are proved in the solid state by single-crystal X-ray
diffraction analysis.