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Chiral structures created through the adsorption of molecules onto achiral surfaces play pivotal roles in many fields of science and engineering, serving a variety of applications. Here we present a systematic study of a novel chiral phenomenon on a surface in terms of organizational chirality, i.e., meso-isomerism, through coverage-driven hierarchical polymorphic transitions of supramolecular assemblies of highly symmetric π-conjugated molecules. Four coverage-dependent phases of dehydrobenzoannulene 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, which may contribute to potential applications related to tailoring chiral surfaces for purposes.
This article was published in the following journal.
Name: Angewandte Chemie (International ed. in English)
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