Jump to main content
Jump to site search

Issue 5, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

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., 2017,4, 882-890
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements