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

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7591-7594
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number21
DOIs
Publication statusPublished - May 28 2014

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Pyrroles
Protonation
Pyridine
Deprotonation
Porphyrins
Conformations
Ion exchange
Nuclear magnetic resonance
X-Rays
X rays
Atoms
pyridine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Zhang, Z., Cha, W. Y., Williams, N. J., Rush, E. L., Ishida, M., Lynch, V. M., ... Sessler, J. L. (2014). Cyclo[6]pyridine[6]pyrrole: A dynamic, twisted macrocycle with no meso bridges. Journal of the American Chemical Society, 136(21), 7591-7594. https://doi.org/10.1021/ja503451m

Cyclo[6]pyridine[6]pyrrole : A dynamic, twisted macrocycle with no meso bridges. / Zhang, Zhan; Cha, Won Young; Williams, Neil J.; Rush, Elise L.; Ishida, Masatoshi; Lynch, Vincent M.; Kim, Dongho; Sessler, Jonathan L.

In: Journal of the American Chemical Society, Vol. 136, No. 21, 28.05.2014, p. 7591-7594.

Research output: Contribution to journalArticle

Zhang, Z, Cha, WY, Williams, NJ, Rush, EL, Ishida, M, Lynch, VM, Kim, D & Sessler, JL 2014, 'Cyclo[6]pyridine[6]pyrrole: A dynamic, twisted macrocycle with no meso bridges', Journal of the American Chemical Society, vol. 136, no. 21, pp. 7591-7594. https://doi.org/10.1021/ja503451m
Zhang, Zhan ; Cha, Won Young ; Williams, Neil J. ; Rush, Elise L. ; Ishida, Masatoshi ; Lynch, Vincent M. ; Kim, Dongho ; Sessler, Jonathan L. / Cyclo[6]pyridine[6]pyrrole : A dynamic, twisted macrocycle with no meso bridges. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 21. pp. 7591-7594.
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