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Pentadecaphenylenes: synthesis, self-assembly and complexation with fullerene C60

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Abstract

Triangular macrocyclic pentadecaphenylenes have been synthesized in moderate yields by the electron-transfer oxidation of the corresponding Lipshutz cuprates with duroquinone. Pentadecaphenylenes are very stable to light, atmospheric oxygen and prolonged heating. Despite the rigid twisted frame, pentadecaphenylenes self-assemble into various nanostructured polymorphs in the solid state. Hexaoctylpentadecaphenylene 1a acts as a gelator in benzene or toluene to form a gel, although 1a neither has a planar structure nor undergoes heteroatom substitution to assist intermolecular interaction. Furthermore, 1a incorporated fullerene C60 into its cavity to afford a fibrous 2 : 1 sandwich complex (1a–C601a) which showed higher gelation ability than 1a itself. Interestingly, Janus-faced 1a acts as a host of two C60 molecules, and an additional C60 was intercalated into the 1a·C60 (2 : 1) complex to form a 1 : 1 complex with an infinite chain structure like –1a–C601a–C60–, which enhances the gelation power of the 1a·C60 sandwich complex.

Graphical abstract: Pentadecaphenylenes: synthesis, self-assembly and complexation with fullerene C60

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Publication details

The article was received on 03 Apr 2017, accepted on 16 Apr 2017 and first published on 17 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00258K
Citation: Org. Chem. Front., 2017, Advance Article
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    Pentadecaphenylenes: synthesis, self-assembly and complexation with fullerene C60

    M. J. Rahman, H. Shimizu, M. Hasegawa and M. Iyoda, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00258K

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