C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State

Georghiou PE, Dawe LN, Tran H-A, Struebe J, Neumann B, Stammler H-G, Kuck D (2008)
JOURNAL OF ORGANIC CHEMISTRY 73(22): 9040-9047.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Various tribenzotriquinacenes (TBTQs), most of which incorporate six functional groups at the periphery of their C-3v-symmetrical, rigid and convex-concave molecular framework, have been studied with respect. to their ability to form supramolecular complexes with the C-60 and C-70 fullerenes, either in the solid state or in solution. The hexabromo derivative Br-6-TBTQ was cocrystallized with C-60 as [Br-6-TBTQ subset of C60 center dot toluene] in benzene, toluene, but, as studied by UV/vis and H-1 NMR spectroscopy, aggregation in benzene, toluene, or carbon disulfide solutions was not observed. Likewise, in contrast to the related C-5v-symmetrical decakis(alkylthio)corannulenes, neither the parent hydrocarbon, nor a related hexamethoxy, or two hexakis(alkylthio) derivatives exhibited color, or complexation-induced chemical shift (CIS) changes with C-60 or C-70. The novel tris(2,3-thianthreno)triquinacene (o-S2C6H4)(3)-TBTQ, a TBTQ derivative extended by three 1,2-benzodithiino wings, and synthesized from Br-6-TBTQ, was found to form 1:1 complexes with C-60 and C-70 in both benzene and toluene solutions. Association constants were determined for the respective complexes, viz. (o-S2C6H4)(3)-TBTQ subset of C-60 (K-assoc = 977 +/- 56) and (o-S2C6H4)(3)-TBTQ subset of C-70 (463 +/- 49, both in benzene). The X-ray single crystal and molecular structures of the pure host and of the aggregates [(o-S2C6H4)(3)-TBTQ subset of 2 C-60 center dot 2.5 chlorobenzene] were also determined.
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Zeitschriftentitel
JOURNAL OF ORGANIC CHEMISTRY
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73
Zeitschriftennummer
22
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9040-9047
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Georghiou PE, Dawe LN, Tran H-A, et al. C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State. JOURNAL OF ORGANIC CHEMISTRY. 2008;73(22):9040-9047.
Georghiou, P. E., Dawe, L. N., Tran, H. - A., Struebe, J., Neumann, B., Stammler, H. - G., & Kuck, D. (2008). C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State. JOURNAL OF ORGANIC CHEMISTRY, 73(22), 9040-9047. doi:10.1021/jo801782z
Georghiou, P. E., Dawe, L. N., Tran, H. - A., Struebe, J., Neumann, B., Stammler, H. - G., and Kuck, D. (2008). C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State. JOURNAL OF ORGANIC CHEMISTRY 73, 9040-9047.
Georghiou, P.E., et al., 2008. C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State. JOURNAL OF ORGANIC CHEMISTRY, 73(22), p 9040-9047.
P.E. Georghiou, et al., “C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State”, JOURNAL OF ORGANIC CHEMISTRY, vol. 73, 2008, pp. 9040-9047.
Georghiou, P.E., Dawe, L.N., Tran, H.-A., Struebe, J., Neumann, B., Stammler, H.-G., Kuck, D.: C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State. JOURNAL OF ORGANIC CHEMISTRY. 73, 9040-9047 (2008).
Georghiou, Paris E., Dawe, Louise N., Tran, Huu-Anh, Struebe, Joerg, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “C-3v-Symmetrical Tribenzotriquinacenes as Hosts for C-60 and C-70 in Solution and in the Solid State”. JOURNAL OF ORGANIC CHEMISTRY 73.22 (2008): 9040-9047.

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