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

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 intersubu...

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Bibliographic Details
Published in:	Journal of the American Chemical Society Vol. 134; no. 9; pp. 4076 - 4080
Main Authors:	Zhan Zhang, Jong Min Lim, Ishida, Masatoshi, Roznyatovskiy, Vladimir V., Lynch, Vincent M., Han-Yuan Gong, Xiaoping Yang, Dongho Kim, Sessler, Jonathan L.
Format:	Article
Published:	American Chemical Society 3/7/2012
Subjects:	Pyrroles Chemical synthesis Proton transfer reactions Macrocyclic compound synthesis Bioconjugates Coupling reactions (Chemistry) Optical spectroscopy X-ray diffraction
Online Access:	View this record in EBSCOhost

Description
Summary:	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.