Cyclo[m]pyridine[n]pyrroles: Hybrid Macrocycles That Display Expanded π-Conjugation upon Protonation
Journal of the American Chemical Society2012Vol. 134(9), pp. 4076–4079
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Zhan Zhang, Jong Min Lim, Masatoshi Ishida, Vladimir V. Roznyatovskiy, Vincent M. Lynch, Han-Yuan Gong, Xiaoping Yang, Dongho Kim, Jonathan L. Sessler
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.
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