Square tiling by square macrocycles at the liquid/solid interface: Co-crystallisation with one- or two-dimensional order

Kazukuni Tahara*, Jun Gotoda, Calden N. Carroll, Keiji Hirose, Steven Defeyter, Tobe Yoshito

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

We have systematically investigated the self-assembled monolayers of seven bimolecular mixtures of square-shaped pyridinophanes and cyclophanes bearing alkoxy or alkoxycarbonyl substituents in the presence of the tropylium ion as a marker of pyridinophanes at liquid/graphite interfaces by means of scanning tunnelling microscopy (STM). The purpose of this work was to elucidate the mixing behaviour of these macrocycles highlighting the formation of one- or two-dimensionally ordered square tilings consisting of alternating alignments of different macrocycles as a result of attractive dipole-dipole or hydrogen-bonding interactions; four co-crystals differing in the dimensionality of the ordering of pyridinophane and cyclophane were observed. The different modes of interaction between the functional groups (ether or carbonyl group) in the side-chains of the pyridinophanes and cyclophanes lead to the formation of co-crystals with dimensionally different orderings of the two macrocycles. These observations revealed that a slight modification of the molecular structure may dramatically change the mixing behaviour and structures of the co-crystals. Tiled surface! STM of the self-assembled monolayers of seven bimolecular mixtures of square-shaped macrocycles bearing different substituents at a liquid/graphite interface revealed the formation of four co-crystals that differ in the dimensionality of the ordering of the two macrocycles due to different modes of interaction between the functional groups in the side-chains (see figure).

Original languageEnglish
Pages (from-to)6806-6816
Number of pages11
JournalChemistry - A European Journal
Volume21
Issue number18
DOIs
StatePublished - 27 Apr 2015

Keywords

  • dipole-dipole interactions
  • macrocycles
  • scanning probe microscopy
  • self-assembly
  • surface analysis

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