Beuerle F, Hirsch A (2009)
Publication Type: Journal article, Original article
Publication year: 2009
Original Authors: Beuerle F., Hirsch A.
Publisher: Wiley-VCH Verlag
Book Volume: 15
Pages Range: 7434-7446
Journal Issue: 30
e,e,e-Trisadducts 13 and 15 have been prepared by a highly regioselective threefold cyclopropanation of tripodal malonates 10 and 12 with C. The yield and regioselectivity depend on the length and structure of the tethers that connect the malonate units to the focal benzene core of 13-15. As a consequence of the template-directed synthesis, all ce.e-trisadducts were formed as in/out isomers exclusively and contain two spherically well-defined addend zones with equatorial and polar orientation, respectively. By variation of the outer malonate termini of the tethers, selective functionalization of the equatorial addend zone could be achieved, thus leading to fine-tuning of intermolecular interactions, such as solubility or aggregation phenomena. After removal of the focal benzene moiety in 14 and 15, selective functionalization of the polar addend zone could be achieved. Strong intramolecular hydrogen-bonding networks of the polar substituents in the polar addend zone could be observed by H NMR spectroscopic analysis. By orthogonal functionalization of both addend zones, fullerene derivatives 44-48 could be synthesized as one single in/out isomer, thus greatly enhancing the potential of e,e,e-trisadducts as building blocks in supramolecular architectures. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
APA:
Beuerle, F., & Hirsch, A. (2009). Synthesis and orthogonal functionalization of [60]fullerene e,e,e-trisadducts with two spherically defined addend zones. Chemistry - A European Journal, 15(30), 7434-7446. https://doi.org/10.1002/chem.200900329
MLA:
Beuerle, Florian, and Andreas Hirsch. "Synthesis and orthogonal functionalization of [60]fullerene e,e,e-trisadducts with two spherically defined addend zones." Chemistry - A European Journal 15.30 (2009): 7434-7446.
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