Efficient Synthesis ofC2v-Symmetrical Pentakisadducts of C60as Versatile Building Blocks for Fullerene Architectures that Involve a Mixed Octahedral Addition Pattern
| Autor: | Frank Hampel, Andreas Hirsch, Wolfgang Donaubauer, Frank Hörmann |
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| Rok vydání: | 2012 |
| Předmět: |
Fullerene
Molecular Structure Chemistry Organic Chemistry Regioselectivity Isoxazoles General Chemistry Carbon-13 NMR Photochemistry Combinatorial chemistry Catalysis Cycloaddition Electron transfer X-Ray Diffraction Cyclization Spectrometry Mass Matrix-Assisted Laser Desorption-Ionization Proton NMR Molecule Moiety Fullerenes Chromatography High Pressure Liquid |
| Zdroj: | Chemistry - A European Journal. 18:3329-3337 |
| ISSN: | 0947-6539 |
| Popis: | We report here on the selective synthesis of fullerene pentakisadducts 3 with an incomplete octahedral addition pattern by means of mixed [5:1]hexakisadducts 1 that involve an isoxazoline moiety as a protection group. The isoxazoline addend can be cleanly cleaved by irradiation with light. By using this protection-deprotection strategy, a variety of fullerene pentakisadducts 3 were synthesized in 29-44% overall yield without the need of HPLC purification. This novel photolytic deprotection of 1 can be explained by an initial electron transfer that leads to a biradical, which can easily eliminate the isoxazoline added. The very efficient and straightforward syntheses of the bisfullerene 4 and the globular hexakisadduct 7, each of which involves mixed octahedral addition patterns, clearly demonstrate the advantage of fullerene pentakisadducts 3 as suitable precursors for the construction of highly functional and complex [5:1]hexakisadduct architectures. Complete structural characterization of all new compounds was carried out by MALDI mass spectrometry, UV/Vis, FTIR, (1)H NMR and (13)C NMR spectroscopy, as well as X-ray diffraction. |
| Databáze: | OpenAIRE |
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