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 | |
| Publication status | Published - 2011 Oct 21 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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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 journal › Article
TY - JOUR
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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U2 - 10.1021/ol2023449
DO - 10.1021/ol2023449
M3 - Article
VL - 13
SP - 5620
EP - 5623
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 20
ER -