Molecular programming of organogelators which can accept [60]fullerene by encapsulation

Michihiro Shirakawa, Norifumi Fujita, Hisashi Shimakoshi, Yoshio Hisaeda, Seiji Shinkai

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

New porphyrin-based gelators bearing eight hydrogen-bond-forming amide groups at their periphery were synthesized. They acted as versatile gelators for aromatic solvents. SEM and TEM observations and X-ray crystallographic analysis established that they tend to aggregate into a two-dimensional sheet-like structure utilizing the intermolecular hydrogen-bonding interaction. In this structure the porphyrin-porphyrin π-π stacking interaction is not involved because of the energetically-predominant hydrogen-bonding interactions, keeping the space distance of 12.9 Å. Very interestingly, when C60 was added, the morphology was transformed to a one-dimensional fibrous structure, which can enjoy a porphyrin-C60-porphyrin interaction. This multicapsular structure having porphyrin-based compartments for hosting C 60 was further characterized by XRD, EPR of a Cu(II) analogue, and the theoretical calculation. Thus, this paper presents a new concept, 'molecular recognition in gel', which is effective for the weak host-guest interaction.

Original languageEnglish
Pages (from-to)2016-2024
Number of pages9
JournalTetrahedron
Volume62
Issue number9
DOIs
Publication statusPublished - Feb 27 2006

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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