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On‐Surface Evolution of meso ‐Isomerism in Two‐Dimensional Supramolecular Assemblies
Author(s) -
Park Juyeon,
Kim JuHyung,
Bak Sunmi,
Tahara Kazukuni,
Jung Jaehoon,
Kawai Maki,
Tobe Yoshito,
Kim Yousoo
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201904290
Subject(s) - supramolecular chemistry , supramolecular chirality , chirality (physics) , enantiomer , molecule , annulene , chemical physics , materials science , phase transition , chemistry , nanotechnology , stereochemistry , organic chemistry , physics , chiral symmetry breaking , condensed matter physics , quantum mechanics , nambu–jona lasinio model , quark
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.