1,3-Dioxopyrrolo[3,4-b]porphyrins: Synthesis and Chemistry

A novel 1,3-dioxopyrrolo[3,4-b]porphyrin (2) has been synthesized in 70% yield following a [4 + 2] cycloaddition reaction of pyrrolo[3,4-b]porphyrin 1 with 1O2. The new imide was used as a template to other 1,3-dioxopyrrolo[3,4-b]porphyrins and to the corresponding open counterparts. The UV/vis abso...

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Bibliographic Details
Published in:Organic letters 2011-01, Vol.13 (1), p.130-133
Main Authors: Carvalho, Carla M. B, Neves, Maria G. P. M. S, Tomé, Augusto C, Paz, Filipe A. Almeida, Silva, Artur M. S, Cavaleiro, José A. S
Format: Article
Language:English
Subjects:
Models, Molecular
Molecular Structure
Oxygen Compounds - chemistry
Porphyrins - chemical synthesis
Pyrroles - chemistry
X-Ray Diffraction
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Summary:A novel 1,3-dioxopyrrolo[3,4-b]porphyrin (2) has been synthesized in 70% yield following a [4 + 2] cycloaddition reaction of pyrrolo[3,4-b]porphyrin 1 with 1O2. The new imide was used as a template to other 1,3-dioxopyrrolo[3,4-b]porphyrins and to the corresponding open counterparts. The UV/vis absorption spectra of the new compounds show significant red-shifts when compared with those of the nonsubstituted analogues. The structure of an imide derivative was confirmed by single-crystal X-ray diffraction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102691s