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

doi:10.1021/ol2023449

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

24 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 language	English
Pages (from-to)	5620-5623
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	20
DOIs	https://doi.org/10.1021/ol2023449
Publication status	Published - 2011 Oct 21

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2023449

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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.",

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T1 - π-extension in expanded porphyrins

T2 - Cyclo[4]naphthobipyrrole

AU - Roznyatovskiy, Vladimir V.

AU - Lim, Jong Min

AU - Lynch, Vincent M.

AU - Lee, Byung Sun

AU - Kim, Dongho

AU - Sessler, Jonathan L.

PY - 2011/10/21

Y1 - 2011/10/21

N2 - 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.

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

Abstract

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