First Synthesis of the Inherently Chiral Trans-4′ Bisadduct of C59N Azafullerene by Using Cyclo-[2]-dodecylmalonate as a Tether |
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| Authors: | Karam Asad Dr Anastasios Stergiou Dr Andreas Kourtellaris Prof Nikos Tagmatarchis Prof Nikos Chronakis |
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| Institution: | 1. Department of Chemistry, University of Cyprus, University str. 1, Building No. 13, 2109 Aglantzia, Nicosia, Cyprus;2. Theoretical and Physical Chemistry Institute, National Hellenic Research Foundation, 48 Vassileos Constantinou Avenue, 11635 Athens, Greece |
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| Abstract: | The multiaddition chemistry of azafullerene C59N has been scarcely explored, and the isolation of pure bisadducts is in its infancy. Encouraged by the recent regioselective synthesis of the inherently chiral equatorialface bisadduct of C59N, we focused on the isolation of the first trans-4 bisadduct in a simple two-step approach. The first regioselective synthesis of the trans-4 bisadduct of C59N by using cyclo-2]-dodecylmalonate as a tether is now reported. The newly synthesized bisadduct has C1 symmetry, as evidenced by 13C NMR, while X-ray crystallography validated the trans-4′ addition pattern. Furthermore, the inherently chiral trans-4′ C59N bisadduct was enantiomerically resolved, and the mirror-image relation of the two enantiomers was probed by circular dichroism spectroscopy. Finally, UV-Vis and redox assays suggested that the addition pattern has a reflection in the light-harvesting and redox properties of the bisadduct. |
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| Keywords: | azafullerenes bisadducts cyclo-[2]-malonates tether-directed remote functionalization regioselectivity |
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