π-extension in expanded porphyrins: Cyclo[4]naphthobipyrrole

Vladimir V. Roznyatovskiy, Jong Min Lim, Vincent M. Lynch, Byung Sun Lee, Dongho Kim, Jonathan L. Sessler

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The π-extended cyclo[4]naphthobipyrrole 1a has been prepared via an Fe(III)-mediated oxidative cyclization of an alkyl-substituted naphthobipyrrole. The structure of this new expanded porphyrin, isolated as the deprotonated sulfate salt, was characterized by spectroscopic means, as well through a single crystal X-ray diffraction analysis. Salt 1a displays a total of four well-resolved redox waves as determined by cyclic voltammetry. It also displays bathochromically shifted near-IR absorption maxima compared to the diprotonated forms of nonannulated cyclo[8]pyrroles.

Original languageEnglish
Pages (from-to)5620-5623
Number of pages4
JournalOrganic Letters
Volume13
Issue number20
DOIs
Publication statusPublished - 2011 Oct 21

Fingerprint

Porphyrins
porphyrins
Salts
salts
Pyrroles
Cyclization
pyrroles
X-Ray Diffraction
X ray diffraction analysis
Sulfates
Cyclic voltammetry
Oxidation-Reduction
sulfates
Single crystals
single crystals
diffraction
x rays

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Roznyatovskiy, V. V., Lim, J. M., Lynch, V. M., Lee, B. S., Kim, D., & Sessler, J. L. (2011). π-extension in expanded porphyrins: Cyclo[4]naphthobipyrrole. Organic Letters, 13(20), 5620-5623. https://doi.org/10.1021/ol2023449
Roznyatovskiy, Vladimir V. ; Lim, Jong Min ; Lynch, Vincent M. ; Lee, Byung Sun ; Kim, Dongho ; Sessler, Jonathan L. / π-extension in expanded porphyrins : Cyclo[4]naphthobipyrrole. In: Organic Letters. 2011 ; Vol. 13, No. 20. pp. 5620-5623.
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Roznyatovskiy, VV, Lim, JM, Lynch, VM, Lee, BS, Kim, D & Sessler, JL 2011, 'π-extension in expanded porphyrins: Cyclo[4]naphthobipyrrole', Organic Letters, vol. 13, no. 20, pp. 5620-5623. https://doi.org/10.1021/ol2023449

π-extension in expanded porphyrins : Cyclo[4]naphthobipyrrole. / Roznyatovskiy, Vladimir V.; Lim, Jong Min; Lynch, Vincent M.; Lee, Byung Sun; Kim, Dongho; Sessler, Jonathan L.

In: Organic Letters, Vol. 13, No. 20, 21.10.2011, p. 5620-5623.

Research output: Contribution to journalArticle

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AU - Roznyatovskiy, Vladimir V.

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AU - Kim, Dongho

AU - Sessler, Jonathan L.

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AB - The π-extended cyclo[4]naphthobipyrrole 1a has been prepared via an Fe(III)-mediated oxidative cyclization of an alkyl-substituted naphthobipyrrole. The structure of this new expanded porphyrin, isolated as the deprotonated sulfate salt, was characterized by spectroscopic means, as well through a single crystal X-ray diffraction analysis. Salt 1a displays a total of four well-resolved redox waves as determined by cyclic voltammetry. It also displays bathochromically shifted near-IR absorption maxima compared to the diprotonated forms of nonannulated cyclo[8]pyrroles.

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Roznyatovskiy VV, Lim JM, Lynch VM, Lee BS, Kim D, Sessler JL. π-extension in expanded porphyrins: Cyclo[4]naphthobipyrrole. Organic Letters. 2011 Oct 21;13(20):5620-5623. https://doi.org/10.1021/ol2023449