Fullerene bisadduct regioisomers containing an asymmetric diamide tether
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Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-41cis-2 was 1.0:1.9:1.5:4.9. Morphology of self-assembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy.
Keywords:bis(pyrrolidino)fullerene regioisomers / Prato's cycloaddition / Hexamethylene-Gly-Gaba diamide tether / NMR analysis / Self-ordering
Source:Tetrahedron, 2017, 73, 50, 7073-7078
- Pergamon-Elsevier Science Ltd, Oxford