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

abstract

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 O-1(2). 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.

keywords

1,3-DIPOLAR CYCLOADDITION REACTIONS; DIELS-ALDER REACTIONS; CAMBRIDGE STRUCTURAL DATABASE; NONPLANAR PORPHYRINS; FUSED CHLORINS; BACTERIOCHLORINS

subject category

Chemistry

authors

Carvalho, CMB; Neves, MGPMS; Tome, AC; Paz, FAA; Silva, AMS; Cavaleiro, JAS

our authors

acknowledgements

Thanks are due to the Universidade de Aveiro, Fundacao para a Ciencia e a Tecnologia (FCT) for specific funding toward the purchase of the single-crystal diffractometer and FEDER for funding the Organic Chemistry Research Unit and the Project PTDC/QUI/74150/2006. C.M.B.C. thanks FCT for the PhD grant SFRH/BD/38611/2007.

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