A Dipyrrin Programmed for Covalent Loading with Fullerenes
| Autor: | Bernhard Kräutler, Chengjie Li, Klaus Wurst |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Fullerene
Diene 010402 general chemistry C60-fullerene porphyrins 01 natural sciences Catalysis chemistry.chemical_compound Polymer chemistry Diels–Alder reactions cycloaddition 010405 organic chemistry Communication Organic Chemistry Thermal decomposition General Chemistry Cheletropic reaction Cycloaddition Communications 0104 chemical sciences cheletropic reaction chemistry Synthetic Methods | Hot Paper Covalent bond Yield (chemistry) Surface modification |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 |
| Popis: | We describe here a di‐(β,β′‐sulfoleno)pyrrin programmed for efficient and specific β,β′‐functionalization via [4+2] cycloaddition reactions. At 120 °C and in the presence of an excess of C60‐fullerene the di‐(β,β′‐sulfoleno)pyrrin decomposed cleanly, furnishing a di‐(β,β′‐fullereno)pyrrin and the corresponding monofullereno‐dipyrrin in an overall yield of 96 %. Hence, relatively mild thermolysis of the di‐(β,β′‐sulfoleno)pyrrin induced stepwise extrusion of two equivalents of SO2, producing highly reactive dipyrrin‐β,β′‐diene intermediates readily, providing a very effective path to [4+2]‐cycloadducts. As presented here by the example of the covalent attachment of C60‐fullerene units, a convenient general methodology for the efficient synthesis of covalent dipyrrin β,β′‐cycloadducts is made available. |
| Databáze: | OpenAIRE |
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