Presentation Information

[9a-B32-7]Evaluation of Antiaromatic π-Stacking Interactions at the Molecular Level

〇Shintaro Fujii1, Ryoya Tomida2, Kazuki Nabeyama1, Aoshi Yamane1, Hiroshi Shinokubo2, Tomoaki Nishino1 (1.Science Tokyo, 2.Nagoya Univ.)

Keywords:

antiaromatic molecule,pi-stacking interaction,atomic force microscopy

Antiaromatic molecules have attracted interest as functional materials for molecular electronics because of their unique electronic properties. Recent studies have suggested that stacked antiaromatic systems can exhibit stacked-ring aromaticity, but the intermolecular interactions responsible for this behavior remain poorly understood. In this study, we investigated the intermolecular interactions of antiaromatic Ni(II) norcorrole molecules using atomic force microscopy (AFM) force spectroscopy. Force–distance measurements with a norcorrole-functionalized AFM tip revealed an attractive interaction force of approximately 150 pN between antiaromatic molecules, comparable to the strength of a single hydrogen bond.
These findings provide direct experimental evidence for significant attractive interactions between antiaromatic π-systems and support the stacked-ring aromaticity proposed for stacked norcorrole assemblies. The results provide molecular-level insight into antiaromatic molecular assemblies and their potential applications in molecular electronic materials.