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

Research output: Contribution to journalArticle

82 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

Fingerprint

Porphyrins
Sorting
X-Ray Diffraction
Nitrogen
Dihedral angle
X ray diffraction analysis
Association reactions
Single crystals
Atoms
meso-cinchomeronimide

All Science Journal Classification (ASJC) codes

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

Cite this

Kamada, T., Aratani, N., Ikeda, T., Shibata, N., Higuchi, Y., Wakamiya, A., ... 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
Kamada, Taisuke ; Aratani, Naoki ; Ikeda, Toshiaki ; Shibata, Naoki ; Higuchi, Yoshiki ; Wakamiya, Atsushi ; Yamaguchi, Shigehiro ; Kim, Kil Suk ; Yoon, Zin Seok ; Kim, Dongho ; Osuka, Atsuhiro. / High fidelity self-sorting assembling of meso-cinchomeronimide appended meso-meso linked Zn(II) diporphyrins. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 23. pp. 7670-7678.
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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.",
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Kamada, T, Aratani, N, Ikeda, T, Shibata, N, Higuchi, Y, Wakamiya, A, Yamaguchi, S, Kim, KS, Yoon, ZS, 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, vol. 128, no. 23, pp. 7670-7678. https://doi.org/10.1021/ja0611137

High fidelity self-sorting assembling of meso-cinchomeronimide appended meso-meso linked Zn(II) diporphyrins. / Kamada, Taisuke; Aratani, Naoki; Ikeda, Toshiaki; Shibata, Naoki; Higuchi, Yoshiki; Wakamiya, Atsushi; Yamaguchi, Shigehiro; Kim, Kil Suk; Yoon, Zin Seok; Kim, Dongho; Osuka, Atsuhiro.

In: Journal of the American Chemical Society, Vol. 128, No. 23, 14.06.2006, p. 7670-7678.

Research output: Contribution to journalArticle

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AU - Kamada, Taisuke

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AU - Ikeda, Toshiaki

AU - Shibata, Naoki

AU - Higuchi, Yoshiki

AU - Wakamiya, Atsushi

AU - Yamaguchi, Shigehiro

AU - Kim, Kil Suk

AU - Yoon, Zin Seok

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2006/6/14

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N2 - 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.

AB - 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.

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