American Chemical Society
ja211985k_si_003.cif (52.36 kB)

Cyclo[m]pyridine[n]pyrroles: Hybrid Macrocycles That Display Expanded π-Conjugation upon Protonation

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posted on 2012-03-07, 00:00 authored by Zhan Zhang, Jong Min Lim, Masatoshi Ishida, Vladimir V. Roznyatovskiy, Vincent M. Lynch, Han-Yuan Gong, Xiaoping Yang, Dongho Kim, Jonathan L. Sessler
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.