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 journalArticlepeer-review

72 Citations (Scopus)


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
Issue number9
Publication statusPublished - 2012 Mar 7

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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