[60]Fullerene-motivated organogel formation in a porphyrin derivative bearing programmed hydrogen-bonding sites

Michihiro Shirakawa, Norifumi Fujita, Seiji Shinkai

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133 Citations (Scopus)


A tetraphenylporphyrin (1b) bearing amide groups at the 3,5-positions of the meso-phenyl groups is assembled into a two-dimensional sheetlike structure and acts as an organogelator. When [60]fullerene was added, the sheetlike structure was dramatically changed into a one-dimensional fibrous structure, and both the gelation ability and the gel stability were improved. The stoichiometry between [60]fullerene and 1b was determined to be 1:2. Examination utilizing SEM and TEM observations, UV-vis and ATR IR spectral analyses, and XRD analysis revealed that an amide-amide hydrogen-bonding interaction creates a cavity, the size of which is complementary to that of [60]fullerene, and these cavities are connected by another amide-amide hydrogen-bonding interaction to provide a one-dimensional multicapsular structure. This is a novel example that the superstructure constructed in an organogel system is drastically changed by added [60]fullerene.

Original languageEnglish
Pages (from-to)9902-9903
Number of pages2
JournalJournal of the American Chemical Society
Issue number33
Publication statusPublished - Aug 20 2003

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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