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• W2077017132 startingPage "9100" @default.
• W2077017132 abstract "Abstract The synthesis of a stereochemically pure concave tribenzotriquinacene receptor ( 7 ) for C 60 fullerene, possessing C 3 point group symmetry, by threefold condensation of C 2 ‐symmetric 1,2‐diketone synthons ( 5 ) and a hexaaminotribenzotriquinacene core ( 6 ) is described. The chiral diketone was synthesized in a five‐step reaction sequence starting from C 2 h ‐symmetric 2,6‐di‐ tert ‐butylanthracene. The highly diastereo‐discriminating Diels–Alder reaction of 2,6‐di‐ tert ‐butylanthracene with fumaric acid di(−)menthyl ester, catalyzed by aluminium chloride, is the relevant stereochemistry introducing step. The structure of the fullerene receptor was verified by 1 H and 13 C NMR spectroscopy, mass spectrometry and single crystal X‐ray diffraction. VCD and ECD spectra were recorded, which were corroborated by ab initio DFT calculations, establishing the chiral nature of 7 with about 99.7 % ee , based on the ee (99.9 %) of the chiral synthon ( 1 ). The absolute configuration of 7 could thus be established as all‐ S [(2 S ,7 S ,16 S ,21 S ,30 S ,35 S )‐( 7 )]. Spectroscopic titration experiments reveal that the host forms 1:1 complexes with either pure fullerene (C 60 ) or fullerene derivatives, such as rotor 1′‐(4‐nitrophenyl)‐3′‐(4‐ N , N ‐dimethylaminophenyl)‐pyrazolino[4′,5′:1,2][60]fullerene ( R ). The complex stability constants of the complexes dissolved in CHCl 3 /CS 2 (1:1 vol. %) are K ([ C 60 ⊂ 7 ])=319(±156) M −1 and K ([ R ⊂ 7 ])=110(±50) M −1 . With molecular dynamics simulations using a first‐principles parameterized force field the asymmetry of the rotational potential for [ R ⊂ 7 ] was shown, demonstrating the potential suitability of receptor 7 to act as a stator in a unidirectionally operating nanoratchet." @default.
• W2077017132 created "2016-06-24" @default.
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• W2077017132 date "2014-06-25" @default.
• W2077017132 modified "2023-10-18" @default.
• W2077017132 title "Tribenzotriquinacene Receptors for C₆₀ Fullerene Rotors: Towards<i>C</i>₃Symmetrical Chiral Stators for Unidirectionally Operating Nanoratchets" @default.
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• W2077017132 doi "https://doi.org/10.1002/chem.201304980" @default.
• W2077017132 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24965605" @default.
• W2077017132 hasPublicationYear "2014" @default.
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