On-Surface Evolution of meso-Isomerism in Two-Dimensional Supramolecular Assemblies

Juyeon Park, Ju Hyung Kim*, Sunmi Bak, Kazukuni Tahara, Jaehoon Jung, Maki Kawai, Yoshito Tobe, Yousoo Kim

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

3 Scopus citations


Chiral structures created through the adsorption of molecules onto achiral surfaces play pivotal roles in many fields of science and engineering. Here, we present a systematic study of a novel chiral phenomenon on a surface in terms of organizational chirality, that is, meso-isomerism, through coverage-driven hierarchical polymorphic transitions of supramolecular assemblies of highly symmetric π-conjugated molecules. Four coverage-dependent phases of dehydrobenzo[12]annulene were uniformly fabricated on Ag(111), exhibiting unique chiral characteristics from the single-molecule level to two-dimensional supramolecular assemblies. All coverage-driven phase transitions stem from adsorption-induced pseudo-diastereomerism, and our observation of a lemniscate-type (∞) supramolecular configuration clearly reveals a drastic chiral phase transition from an enantiomeric chiral domain to a meso-isomeric achiral domain. These findings provide new insights into controlling two-dimensional chiral architectures on surfaces.

Original languageEnglish
Pages (from-to)9611-9618
Number of pages8
JournalAngewandte Chemie - International Edition
Issue number28
StatePublished - 8 Jul 2019


  • chirality
  • nanostructures
  • scanning tunneling microscopy
  • self-assembly
  • surface chemistry

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