Quinoxaline-bridged porphyrinoids

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

Research output: Contribution to journalArticle

158 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)13474-13479
Number of pages6
JournalJournal of the American Chemical Society
Volume124
Issue number45
DOIs
Publication statusPublished - Nov 13 2002

Fingerprint

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

Cite this

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.

In: Journal of the American Chemical Society, Vol. 124, No. 45, 13.11.2002, p. 13474-13479.

Research output: Contribution to journalArticle

Sessler, JL, Maeda, H, Mizuno, T, Lynch, VM & Furuta, H 2002, 'Quinoxaline-bridged porphyrinoids', Journal of the American Chemical Society, vol. 124, no. 45, pp. 13474-13479. https://doi.org/10.1021/ja0273750
Sessler JL, Maeda H, Mizuno T, Lynch VM, Furuta H. Quinoxaline-bridged porphyrinoids. Journal of the American Chemical Society. 2002 Nov 13;124(45):13474-13479. https://doi.org/10.1021/ja0273750
Sessler, Jonathan L. ; Maeda, Hiromitsu ; Mizuno, Toshihisa ; Lynch, Vincent M. ; Furuta, Hiroyuki. / Quinoxaline-bridged porphyrinoids. In: Journal of the American Chemical Society. 2002 ; Vol. 124, No. 45. pp. 13474-13479.
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