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A Dipyrrin Programmed for Covalent Loading with Fullerenes
Author(s) -
Li Chengjie,
Wurst Klaus,
Kräutler Bernhard
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801995
Subject(s) - fullerene , covalent bond , chemistry , cycloaddition , yield (engineering) , combinatorial chemistry , organic chemistry , materials science , metallurgy , catalysis
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 C 60 ‐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 SO 2 , 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 C 60 ‐fullerene units, a convenient general methodology for the efficient synthesis of covalent dipyrrin β,β′‐cycloadducts is made available.