Cyclo[m]pyridine[n]pyrroles

Hybrid macrocycles that display expanded π-conjugation upon protonation

Zhan Zhang, Jong Min Lim, Masatoshi Ishida, Vladimir V. Roznyatovskiy, Vincent M. Lynch, Han Yuan Gong, Xiaoping Yang, Dongho Kim, Jonathan L. Sessler

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

Novel hybrid cyclo[m]pyridine[n]pyrroles have been synthesized using Suzuki coupling. Their NMR and optical spectroscopic features and solid state structural parameters provide support for the proposal that these species are best described as locally aromatic compounds devoid of long-range intersubunit conjugation. However, an extension of the π-conjugation in the macrocycles can be realized through protonation, as inferred from optical spectroscopic and X-ray diffraction-based structural studies.

Original languageEnglish
Pages (from-to)4076-4079
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number9
DOIs
Publication statusPublished - Mar 7 2012
Externally publishedYes

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Pyrroles
Aromatic compounds
Protonation
X-Ray Diffraction
Pyridine
Nuclear magnetic resonance
X ray diffraction
pyridine

All Science Journal Classification (ASJC) codes

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

Cite this

Cyclo[m]pyridine[n]pyrroles : Hybrid macrocycles that display expanded π-conjugation upon protonation. / Zhang, Zhan; Lim, Jong Min; Ishida, Masatoshi; Roznyatovskiy, Vladimir V.; Lynch, Vincent M.; Gong, Han Yuan; Yang, Xiaoping; Kim, Dongho; Sessler, Jonathan L.

In: Journal of the American Chemical Society, Vol. 134, No. 9, 07.03.2012, p. 4076-4079.

Research output: Contribution to journalArticle

Zhang, Z, Lim, JM, Ishida, M, Roznyatovskiy, VV, Lynch, VM, Gong, HY, Yang, X, Kim, D & Sessler, JL 2012, 'Cyclo[m]pyridine[n]pyrroles: Hybrid macrocycles that display expanded π-conjugation upon protonation', Journal of the American Chemical Society, vol. 134, no. 9, pp. 4076-4079. https://doi.org/10.1021/ja211985k
Zhang, Zhan ; Lim, Jong Min ; Ishida, Masatoshi ; Roznyatovskiy, Vladimir V. ; Lynch, Vincent M. ; Gong, Han Yuan ; Yang, Xiaoping ; Kim, Dongho ; Sessler, Jonathan L. / Cyclo[m]pyridine[n]pyrroles : Hybrid macrocycles that display expanded π-conjugation upon protonation. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 9. pp. 4076-4079.
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