Issue 5, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
03 Ebr. 2017
Accepted
16 Ebr. 2017
First published
17 Ebr. 2017

Org. Chem. Front., 2017,4, 882-890

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

M. J. Rahman, H. Shimizu, M. Hasegawa and M. Iyoda, Org. Chem. Front., 2017, 4, 882 DOI: 10.1039/C7QO00258K

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