A Dipyrrin Programmed for Covalent Loading with Fullerenes

作者：Li, Chengjie; Wurst, Klaus; Kraeutler, Bernhard

来源：Chemistry - A European Journal, 2018, 24(40): 10032-10037.

DOI：10.1002/chem.201801995

• C-60-fullerene
• cheletropic reaction
• cycloaddition
• Diels-Alder reactions
• porphyrins

We describe here a di-(,-sulfoleno)pyrrin programmed for efficient and specific ,-functionalization via [4+2] cycloaddition reactions. At 120 degrees C and in the presence of an excess of C-60-fullerene the di-(,-sulfoleno)pyrrin decomposed cleanly, furnishing a di-(,-fullereno)pyrrin and the corresponding monofullereno-dipyrrin in an overall yield of 96%. Hence, relatively mild thermolysis of the di-(,-sulfoleno)pyrrin induced stepwise extrusion of two equivalents of SO2, producing highly reactive dipyrrin-,-diene intermediates readily, providing a very effective path to [4+2]-cycloadducts. As presented here by the example of the covalent attachment of C-60-fullerene units, a convenient general methodology for the efficient synthesis of covalent dipyrrin ,-cycloadducts is made available.

• 出版日期2018-7-17
• 单位华东理工大学