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

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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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    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