Synthesis and characterization of water-soluble amino fullerene derivatives

Org Lett. 2000 Apr 20;2(8):1011-4. doi: 10.1021/ol990312a.


[formula: see text] A series of amino-substituted methanofullerene derivatives were prepared by mono-, tris-, and hexa-Bingel-Hirsch reactions using an N-protected malonate derivative. Upon scission of the protecting groups, the e,e,e-tris- and octahedral Th hexa-methano amino fullerenes were found to be among the most water-soluble fullerene derivatives yet prepared. 3He NMR data on corresponding adducts of 3He/C60 helped verify the assigned structures. UV spectral studies confirmed the influence of aggregation on solubility of these adducts in water.