Chemistry of anthracene-acetylene oligomers XXV: On-surface chirality of a self-assembled molecular network of a fan-blade-shaped anthracene-acetylene macrocycle with a long alkyl chain

Takuya Tsuya, Kohei Iritani, Kazukuni Tahara, Yoshito Tobe, Tetsuo Iwanaga, Shinji Toyota*

*Corresponding author for this work

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

An anthracene cyclic dimer with two different linkers and a dodecyl group was synthesized by means of coupling reactions. The calculated structure had a planar macrocyclic π core and a linear alkyl chain. Scanning tunneling microscopy observations at the 1-phenyloctane/graphite interface revealed that the molecules formed a self-assembled monolayer that consisted of linear striped bright and dark bands. In each domain, the molecular network consisted of either Re or Si molecules that differed in the two-dimensional chirality about the macrocyclic faces, which led to a unique conglomerate-type self-assembly. The molecular packing mode and the conformation of the alkyl chains are discussed in terms of the intermolecular interactions and the interactions between the molecules and the graphite surface with the aid of MM3 simulations of a model system. Networking: A chiral molecular network was constructed from prochiral molecules at the 1-phenyloctane/graphite interface as revealed by STM observations (see figure). The molecular packing mode that involves the chirality and the conformation of the alkyl chain was reasonably simulated by MM3 calculations.

Original languageEnglish
Pages (from-to)5520-5527
Number of pages8
JournalChemistry - A European Journal
Volume21
Issue number14
DOIs
StatePublished - 27 Mar 2015

Keywords

  • chirality
  • molecular modeling
  • oligomers
  • scanning probe microscopy
  • self-assembly

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