Chiral dinaphthylporphyrin with C2 symmetry: synthesis, resolution, and enantio-discrimination by single-crystal X-ray diffraction analysis

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.

Graphical abstractAn intrinsic chiral dinaphthylporphyrin with C2 symmetry has been synthesized and resolved to pure enantiomers. The stereochemistry has been studied by single-crystal X-ray diffraction analysis.Figure optionsDownload full-size imageDownload as PowerPoint slide