Rational Synthesis of 2-Bromoporphyrins and 2,12-Dibromoporphyrins
| Autor: | Anna-Bea Bornhof, Ruisheng Xiong, K. Eszter Borbas |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Bromine
010405 organic chemistry Organic Chemistry Sonogashira coupling chemistry.chemical_element Crystal structure 010402 general chemistry 01 natural sciences 0104 chemical sciences Metal chemistry.chemical_compound chemistry Yield (chemistry) visual_art Polymer chemistry visual_art.visual_art_medium Organic chemistry Absorption (chemistry) Derivative (chemistry) |
| Zdroj: | The Journal of organic chemistry. 82(23) |
| ISSN: | 1520-6904 |
| Popis: | Bromoporphyrins were prepared by the metal-mediated self-condensation of brominated 1-formyldipyrromethanes. Depending on the conditions, Mg(II)-2,12-dibromoporphyrin and Mg(II)-2-bromoporphyrin could be obtained in up to 11% and 17% isolated yield, respectively. Zn(II) was also a viable templating metal. The positions of the bromine substituents were confirmed by 2D-NMR spectroscopic analysis and the X-ray crystal structure of a derivative. Suzuki and Sonogashira reactions of the bromoporphyrins yielded 2-substituted or 2,12-disubstituted porphyrins with red-shifted absorption and emission spectra. This method provides access to the minimalist core of β-mono- and β,β′-disubstituted porphyrins from readily available starting materials. |
| Databáze: | OpenAIRE |
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