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Coordination-Enabled Resolution of Inherently Chiral 1,5-Naphthiporphyrin.

Zhi-Cheng Jia1, Hua-Xi He1, He-Ye Zhou1

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Inorganic Chemistry
|October 21, 2025
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Researchers developed a chiral naphthiporphyrin ligand that, upon rhodium metalation, forms a complex enabling enantiomer resolution. This breakthrough overcomes conformational lability, paving the way for advanced stereocontrol in coordination chemistry.

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Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Chiral Materials

Background:

  • Chiral carbaporphyrins often exhibit conformational lability, hindering enantiomer resolution.
  • Developing rigid chiral scaffolds is crucial for controlling stereochemistry in complex molecules.

Purpose of the Study:

  • To design and synthesize a novel chiral naphthiporphyrin ligand with inherent chirality.
  • To investigate the metalation of the ligand and its impact on conformational stability and enantiomer interconversion.
  • To explore the potential for stereocontrol and multinuclear cluster assembly using this ligand architecture.

Main Methods:

  • Synthesis of a 1,5-naphthiporphyrin ligand (1) featuring three naphthalene units linked by dipyrromethene.
  • Metalation of the ligand with Rh(I) to form a trinuclear complex (1-Rh3).
  • Chromatographic separation of enantiomers using a chiral stationary phase.
  • Characterization of chiroptical properties, including absorption dissymmetry factors.

Main Results:

  • The naphthiporphyrin ligand (1) exhibits inherent chirality but undergoes racemization via curvature inversion.
  • Metalation with Rh(I) forms a trinuclear complex (1-Rh3) that restricts rotation, suppresses racemization, and allows chromatographic resolution.
  • Resolved enantiomers show significant chiroptical responses with high absorption dissymmetry factors (up to 0.038 at 654 nm).
  • The ligand architecture facilitates the assembly of a heteropolynuclear Zn4Na cluster.

Conclusions:

  • The Rh(I) metal centers effectively lock the naphthiporphyrin conformation, enabling stable enantiomers.
  • This work demonstrates a coordination strategy for achieving stereocontrol and constructing complex multinuclear assemblies.
  • The developed chiral scaffold offers a platform for designing molecules with tailored chiroptical properties.