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Chiral dinaphthylporphyrin withC2symmetry: synthesis, resolution, and enantio-discrimination by single-crystal X-ray diffraction analysis

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Volume
55
Issue
22
Identifiers
DOI: 10.1016/j.tetlet.2014.04.067
Keywords
  • Porphyrin
  • Chirality
  • Stereochemistry
  • Crystal Structure
Disciplines
  • Design

Abstract

Abstract An intrinsic chiral dinaphthylporphyrin with C2 symmetry, namely [5,15-trans-bis(2-hydroxynaphthyl)-10-phenyl-20-(4-hydroxyphenyl)porphyrinato]zinc(ІІ) (ZnDNP), has been designed and synthesized. The molecular structure of ZnDNP was determined by single crystal X-ray diffraction analysis. Resolution of the racemic mixture was achieved with chiral HPLC technique. In particular, the stereostructures of the enantiomers and the specific interactions between the chiral meso-dinaphthylporphyrin with l-Phe-OMe were elucidated in the solid state by single-crystal X-ray diffraction analysis.

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