Fullerene bisadduct regioisomers containing an asymmetric diamide tether

• Published in: Tetrahedron Vol. 73; no. 50; pp. 7073 - 7078
• Main Authors: Kop, Tatjana J., Đorđević, Jelena, Bjelaković, Mira S., Milić, Dragana R.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 14-12-2017
• Subjects: bis(pyrrolidino)fullerene regioisomers; Hexamethylene-Gly-Gaba diamide tether; NMR analysis; Prato's cycloaddition; Self-ordering; Prato's cycloaddition; bis(pyrrolidino)fullerene regioisomers; Hexamethylene-Gly-Gaba diamide tether; Self-ordering; NMR analysis
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2017.10.069

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-4/cis-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.
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