On‐Surface Evolution of meso‐Isomerism in Two‐Dimensional Supramolecular Assemblies. (5th June 2019)

• Record Type: Journal Article
• Authors: Park, Juyeon; Kim, Ju‐Hyung; Bak, Sunmi; Tahara, Kazukuni; Jung, Jaehoon; Kawai, Maki; Tobe, Yoshito; Kim, Yousoo
• Is Part Of: Angewandte Chemie. Volume 131:Number 28(2019)
• Page Start: 9713
• Page End: 9720
• Publication Date: 2019-06-05
• Subjects: Chiralität -- Nanostrukturen -- Oberflächenchemie -- Rastertunnelmikroskopie -- Selbstorganisation; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201904290
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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. Abstract : Chiralität in zwei Dimensionen : Die Bildung von meso ‐Isomerie auf Oberflächen durch hierarchische polymorphe Übergänge supramolekularer Anordnungen hochsymmetrischer π‐konjugierter Moleküle wurde beobachtet. Vier vom Bedeckungsgrad abhängige Phasen von Dehydrobenzo[12]annulen wurden auf Ag(111) erzeugt und zeigen einzigartige chirale Charakteristika vom Einzelmolekül‐Niveau bis hin zu supramolekularen 2D‐Anordnungen.