Quinoxaline-bridged porphyrinoids

Jonathan L. Sessler, Hiromitsu Maeda, Toshihisa Mizuno, Vincent M. Lynch, Hiroyuki Furuta

研究成果: ジャーナルへの寄稿記事

158 引用 (Scopus)

抄録

Quinoxaline-bridged porphyrinoids (3), the first macrocycles containing dipyrrolylquinoxaline (DPQ, 1) subunits, were synthesized from the condensation of the diformyl-substituted DPQ derivatives (2) and 1,8-diaminoanthracene. The resulting structures were confirmed by x-ray analyses, which showed encapsulation of CHCl3 molecules within the columnar channels established by the stacked arrangement of the individual macrocycles. The solution phase interactions with fluoride and dihydrogenphosphate anions were studied in the case of the unsubstituted system 3a in CH2Cl2. The binding affinities for these anions, studied at the tetrabutylammonium salts, were found to be enhanced relative to those of the simple, unsubstituted monomeric DPQ "parent" system (1a), presumably as the result of the combined effects of preorganization and cooperative binding permitted by the pyrrole NH donor groups. Positive homotropic allosteric anion binding was observed and is ascribed to the structurally coupled nature of the two binding cavities present in the macrocycles. Support for this latter contention came from energy minimization studies.

元の言語英語
ページ(範囲)13474-13479
ページ数6
ジャーナルJournal of the American Chemical Society
124
発行部数45
DOI
出版物ステータス出版済み - 11 13 2002

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Quinoxalines
Anions
Negative ions
Pyrroles
Fluorides
Encapsulation
Condensation
Salts
X-Rays
Derivatives
X rays
Molecules

All Science Journal Classification (ASJC) codes

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

これを引用

Sessler, J. L., Maeda, H., Mizuno, T., Lynch, V. M., & Furuta, H. (2002). Quinoxaline-bridged porphyrinoids. Journal of the American Chemical Society, 124(45), 13474-13479. https://doi.org/10.1021/ja0273750

Quinoxaline-bridged porphyrinoids. / Sessler, Jonathan L.; Maeda, Hiromitsu; Mizuno, Toshihisa; Lynch, Vincent M.; Furuta, Hiroyuki.

:: Journal of the American Chemical Society, 巻 124, 番号 45, 13.11.2002, p. 13474-13479.

研究成果: ジャーナルへの寄稿記事

Sessler, JL, Maeda, H, Mizuno, T, Lynch, VM & Furuta, H 2002, 'Quinoxaline-bridged porphyrinoids', Journal of the American Chemical Society, 巻. 124, 番号 45, pp. 13474-13479. https://doi.org/10.1021/ja0273750
Sessler, Jonathan L. ; Maeda, Hiromitsu ; Mizuno, Toshihisa ; Lynch, Vincent M. ; Furuta, Hiroyuki. / Quinoxaline-bridged porphyrinoids. :: Journal of the American Chemical Society. 2002 ; 巻 124, 番号 45. pp. 13474-13479.
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