Achieving chiral resolution in self-assembled supramolecular structures through kinetic pathways

Jong Keon Yoon, Won Joon Son, Howon Kim, Kyung Hoon Chung, Seungwu Han, Se-Jong Kahng

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Chiral phase transitions were studied in a self-assembled 2,6-dibromoanthraquinones supramolecular system prepared on Au(111) using scanning tunneling microscopy. As the molecules were deposited at about 150K, they formed heterochiral chevron structures (a racemate) consisting of two alternating prochiral molecular rows. When the as-deposited sample was warmed to 300K followed by cooling to 80K, phase-separated homochiral structures (a conglomerate), as well as the chevron structures, were observed. We propose molecular models for the structures that are in good agreement with abinitio studies and can be explained by hydrogen bonds and halogen bonds. We found that heterochiral chevron structures were more stable than homochiral structures due to two additional halogen bonds per molecule. We considered kinetic pathways for the phase transitions that were made possible via a disordered liquid phase entropically stabilized at 300K. We show how chiral resolution can be achieved by exploiting kinetic paths allowed in supramolecular systems.

Original languageEnglish
Article number275705
JournalNanotechnology
Volume22
Issue number27
DOIs
Publication statusPublished - 2011 Jul 8

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Halogens
Phase Transition
Scanning Tunnelling Microscopy
Phase transitions
Molecules
Kinetics
Molecular Models
Scanning tunneling microscopy
Molecular Structure
Hydrogen
Hydrogen bonds
Cooling
Liquids

ASJC Scopus subject areas

  • Bioengineering
  • Chemistry(all)
  • Electrical and Electronic Engineering
  • Mechanical Engineering
  • Mechanics of Materials
  • Materials Science(all)

Cite this

Achieving chiral resolution in self-assembled supramolecular structures through kinetic pathways. / Yoon, Jong Keon; Son, Won Joon; Kim, Howon; Chung, Kyung Hoon; Han, Seungwu; Kahng, Se-Jong.

In: Nanotechnology, Vol. 22, No. 27, 275705, 08.07.2011.

Research output: Contribution to journalArticle

Yoon, Jong Keon ; Son, Won Joon ; Kim, Howon ; Chung, Kyung Hoon ; Han, Seungwu ; Kahng, Se-Jong. / Achieving chiral resolution in self-assembled supramolecular structures through kinetic pathways. In: Nanotechnology. 2011 ; Vol. 22, No. 27.
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