Systematic studies on structural parameters for nanotubular assembly of hexa-peri-hexabenzocoronenes

Wusong Jin, Yohei Yamamoto, Takanori Fukushima, Noriyuki Ishii, Jungeun Kim, Kenichi Kato, Masaki Takata, Takuzo Aida

Research output: Contribution to journalArticle

123 Citations (Scopus)

Abstract

Thirteen different hexa-peri-hexabenzocoronenes (HBCs) I-III were newly synthesized, and their self-assembling behaviors were investigated. Taking into account also the reported behaviors of amphiphilic HBCs, some structural parameters of HBC essential for the tubular assembly were revealed. Points to highlight include (1) the importance of two phenyl groups attached to one side of the HBC unit, (2) essential roles of long paraffinic side chains on the other side of the phenyl groups, and (3) no necessity of hydrophilic oligo(ethylene glycol) side chains. The hierarchical nanotubular structure, rendered by virtue of a synchrotron radiation technique, was virtually identical to our previous proposal, where the nanotubes are composed of helically coiled bilayer tapes with a tilting angle of ∼45°. Each tape consists of π-stacked HBC units, where the inner and outer HBC layers are connected by interdigitation of paraffinic side chains. The coiled structure is most likely caused by a steric congestion of the phenyl groups attached to the HBC unit, whose tilting direction may determine the handedness of the helically chiral nanotube.

Original languageEnglish
Pages (from-to)9434-9440
Number of pages7
JournalJournal of the American Chemical Society
Volume130
Issue number29
DOIs
Publication statusPublished - 2008 Jul 23
Externally publishedYes

ASJC Scopus subject areas

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

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