Chiral self-discriminative self-assembling of meso-meso linked diporphyrins

Chihiro Maeda, Taisuke Kamada, Naoki Aratani, Atsuhiro Osuka

Research output: Contribution to journalReview articlepeer-review

78 Citations (Scopus)


We have explored a variety of self-assembled cyclic porphyrin arrays mainly as biomimetic models of light harvesting antenna in photosynthetic systems. The key reaction is Ag(I)-promoted coupling reaction of 5,15-diaryl zinc(II) porphyrin that provides a meso-meso linked diporphyrin. meso-Pyridine-appended zinc(II) porphyrins M1-M3 and their meso-meso linked dimers D1-D3 assemble spontaneously in non-coordinating solvents into tetrameric porphyrin squares S1-S3 and porphyrin boxes B1-B3, respectively. In the latter case, it has been demonstrated that four molecules of R-diporphyrin assemble into R-box and four molecules of S-diporphyrin assemble into S-box via rigorous homochiral self-sorting process. Efficient excitation energy transfer along these cyclic porphyrin arrays has been revealed by the time-resolved transient absorption and fluorescence measurements. We have also demonstrated that the meso-cinchomeronimide appended Zn(II) porphyrin CIM forms a cyclic trimer, while the corresponding diporphyrins CID exhibit high-fidelity self-sorting assembling to form discrete cyclic trimer, tetramer, and pentamer with large association constants, through perfect discrimination of enantiomeric and conformational differences of the meso-cinchomeronimide substituents.

Original languageEnglish
Pages (from-to)2743-2752
Number of pages10
JournalCoordination Chemistry Reviews
Issue number21-24
Publication statusPublished - Nov 2007
Externally publishedYes


  • Chiral recognition
  • Porphyrin
  • Self-assembly
  • Self-sorting

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry


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