On‐Surface Evolution of meso‐Isomerism in Two‐Dimensional Supramolecular Assemblies. Issue 28 (6th 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 international edition. Volume 58:Issue 28(2019)
• Page Start: 9611
• Page End: 9618
• Publication Date: 2019-06-06
• Subjects: chirality -- nanostructures -- scanning tunneling microscopy -- self-assembly -- surface chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201904290
• Languages: English
• ISSNs: 1433-7851

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 : Chirality in two dimensions : The formation of meso ‐isomerism on surfaces through coverage‐driven hierarchical polymorphic transitions of supramolecular assemblies of highly symmetric π‐conjugated molecules is reported. Four coverage‐dependent phases of dehydrobenzo[12]annulene were uniformly fabricated on Ag(111) and exhibit unique chiral characteristics from the single‐molecule level to two‐dimensional supramolecular assemblies.