Cyclo[6]pyridine[6]pyrrole: A dynamic, twisted macrocycle with no meso bridges

Zhan Zhang, Won Young Cha, Neil J. Williams, Elise L. Rush, Masatoshi Ishida, Vincent M. Lynch, Dongho Kim, Jonathan L. Sessler

研究成果: Contribution to journalArticle査読

39 被引用数 (Scopus)

抄録

A large porphyrin analogue, cyclo[6]pyridine[6]pyrrole, containing no meso bridging atoms, has been synthesized through Suzuki coupling. In its neutral form, this macrocycle exists as a mixture of two figure-eight conformers that undergo fast exchange in less polar solvents. Upon protonation, the dynamic twist can be transformed into species that adopt a ruffled planar structure or a figure-eight shape depending on the extent of protonation and counteranions. Conversion to a bisboron difluoride complex via deprotonation with NaH and treatment with BF3 acts to lock the macrocycle into a figure-eight conformation. The various forms of cyclo[6]pyridine[6]pyrrole are characterized by distinct NMR, X-ray crystallographic, and spectroscopic features.

本文言語英語
ページ(範囲)7591-7594
ページ数4
ジャーナルJournal of the American Chemical Society
136
21
DOI
出版ステータス出版済み - 5 28 2014

All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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