I searched Google, Google Scholar and SciFinder for it, but I couldn't find any answer.
A. Duarte-Ruiz et al. (A. Duarte-Ruiz, T. Müller, K. Wurst and B. Kräutler, Tetrahedron, 2001, 57, 3709–3714) state that anthracene only forms bis-adducts, where both anthracene molecules don't bind to the same hemisphere of the bucky ball. The closest the two anthracenes get is equatorial. They also identified some tris-adducts.
Following the "not on the same hemisphere"-rule from the bis-adducts I could imagine that there are tetra-, penta- or even hexa-adducts of anthracene and fullerene, but I couldn't find any literature reports. For smaller substituents (like 2,3-dimethyl-1,3-butadiene) these adducts are already known.
If they don't exist: What may be the reason? Are the anthracene molecules to bulky? Or are the higher adducts between anthracene and fullerene unstable (mono-, bis- and tris-adducts decompose slowly)?
Dear Robert,
Yes, there are reported some studies.
Please read the attached papers (tris and hexa).
Best Regards,
Eugenia
Hi Eugenia,
thank you for your answer!
Unfortunately the hexa-adduct is no anthracene adduct, but its based on malonate groups bound to the fullerene.
Meanwhile i found a hint pointing to a tetra-adduct of anthracene and fullerene in the Ph.D. thesis of Duarte-Ruiz from 2000. The abstract reads:
"... Furthermore six new tris-adducts ('t4t4t2', 't3t3t3', 't3t3t4', 'et3t2', 'et3t4', and 'eee') and one tetra-adduct ('eeet3') were separated and characterized. ..."
Best Regards,
Robert
https://inis.iaea.org/search/searchsinglerecord.aspx?recordsFor=SingleRecord&RN=33011486
Hi everyone,
meanwhile I found a publication, where the adducts of fullerene and 9,10-dimethylanthracene were studied by 3He-NMR. (G. Wang et al., J. Am. Chem. Soc., 2001, 123, 256-259)
They found that even at a ratio of 1:12 there were only tetraadducts between fullerene and dimethylanthracene. Its not directly comparable to anthracene/fullerene, but its a hint that penta- and hexaadducts may not be possible between fullerene and anthracene.
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