High fidelity self-sorting assembling of meso-cinchomeronimide appended meso-meso linked Zn(II) diporphyrins

Taisuke Kamada, Naoki Aratani, Toshiaki Ikeda, Naoki Shibata, Yoshiki Higuchi, Atsushi Wakamiya, Shigehiro Yamaguchi, Kil Suk Kim, Zin Seok Yoon, Dongho Kim, Atsuhiro Osuka

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86 Citations (Scopus)

Abstract

In noncoordinating solvents, meso-cinchomeronimide appended Zn(II) porphyrin 2 forms a cyclic trimer, while diporphyrins 7 exhibit high-fidelity self-sorting assembling to form discrete cyclic trimer, tetramer, and pentamer with large association constants from 7in-in, 7in-out, and 7out-out, respectively, through almost perfect discrimination of enantiomeric and conformational differences of the mesocinchomeronimide substituents. In the latter self-sorting processes, the dihedral angles dictated by the two pyridyl nitrogen atoms control the size of the aggregates; the trimer from 7in-in, the tetarmer from 7in-out, and the pentamer from 7out-out. Cyclic structures of (2)3 and (R-7out-out)5 have been determined by single-crystal X-ray diffraction analysis.

Original languageEnglish
Pages (from-to)7670-7678
Number of pages9
JournalJournal of the American Chemical Society
Volume128
Issue number23
DOIs
Publication statusPublished - 2006 Jun 14

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Kamada, T., Aratani, N., Ikeda, T., Shibata, N., Higuchi, Y., Wakamiya, A., Yamaguchi, S., Kim, K. S., Yoon, Z. S., Kim, D., & Osuka, A. (2006). High fidelity self-sorting assembling of meso-cinchomeronimide appended meso-meso linked Zn(II) diporphyrins. Journal of the American Chemical Society, 128(23), 7670-7678. https://doi.org/10.1021/ja0611137