Hörmann F, Donaubauer W, Hampel F, Hirsch A (2012)
Publication Type: Journal article, Original article
Publication year: 2012
Original Authors: Hörmann F., Donaubauer W., Hampel F., Hirsch A.
Publisher: Wiley-VCH Verlag
Book Volume: 18
Pages Range: 3329-3337
Journal Issue: 11
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, H NMR and C NMR spectroscopy, as well as X-ray diffraction. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
APA:
Hörmann, F., Donaubauer, W., Hampel, F., & Hirsch, A. (2012). Efficient synthesis of C 2v-Symmetrical Pentakisadducts of C 60 as versatile building blocks for fullerene architectures that involve a mixed octahedral addition pattern. Chemistry - A European Journal, 18(11), 3329-3337. https://doi.org/10.1002/chem.201102638
MLA:
Hörmann, Frank, et al. "Efficient synthesis of C 2v-Symmetrical Pentakisadducts of C 60 as versatile building blocks for fullerene architectures that involve a mixed octahedral addition pattern." Chemistry - A European Journal 18.11 (2012): 3329-3337.
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