AI Article Synopsis
- The first rational synthesis of 5,10-diazaporphyrins was achieved through nucleophilic substitutions using α,α'-dibromotripyrrin.
- Two nucleophiles, 1,3-diiminoisoindoline and 3,4-di(ethylsulfanyl)pyrrole-2,5-diimine, were utilized to produce 5,10-diazobenzoporphyrin and 5,10-diaza-7,8-di(ethylsulfanyl)porphyrin.
- The resulting compounds were reduced with varying yields, and their structures were confirmed by X-ray crystallography, while their optical and electrochemical properties were compared to other porphyrins.
Article Abstract
We report here the first rational synthesis of 5,10-diazaporphyrins via nucleophilic substitution reactions of α,α'-dibromotripyrrin. Uses of 1,3-diiminoisoindoline and 3,4-di(ethylsulfanyl)pyrrole-2,5-diimine as nucleophiles allowed for synthesis of 5,10-diazabenzoporphyrin () and 5,10-diaza-7,8-di(ethylsulfanyl)porphyrin (3). 3 was reduced to 5,10-diazaporphyrin (), 5,10-diaza-2,3-dihydrogenated porphyrin (), and 5,10-diaza-7,8-dihydrogenated porphyrin () with yields that were dependent upon reduction conditions. All the structures of these products were confirmed by X-ray crystallographic analysis. Their optical and electrochemical properties have been comparatively studied with those of 5,15-diazaporphyrin () and 5,15-diazachlorin (). Furthermore, NH tautomers of and were observed as different species in solution, and the dynamic NH tautomeric behavior was studied in .
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| http://dx.doi.org/10.1021/acs.joc.9b03467 | DOI Listing |
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