MANABIYA Manuscript Understanding the Ring-Flip Mechanism of Overcrowded Ethylenes through an Experimental and Theoretical Approach

The MANABIYA System is a program by which researchers from other institutes, universities and companies can come to ICReDD for a short-term period of training and joint research. The following paper includes contributions that were made possible by the participation of co-author Tomoki Tadokoro in the MANABIYA System. He stayed at ICReDD for four weeks during March 2021 and worked under Prof. Satoshi Maeda, where he learned and used artificial force induced reaction (AFIR) calculations to gain insight into the mechanism of the ring-flip of the anthraquinodimethane derivatives he was working on. During his time in MANABIYA, Tomoki was a 4th year Bachelors student from the lab of Professor Takanori Suzuki and Associate Professor Yusuke Ishigaki in the Department of Chemistry, Faculty of Science at Hokkaido University. He is currently a first-year Masters student at the Graduate School of Chemical Science and Engineering at Hokkaido University.

Molecules that change their structure in response to specific stimuli are attracting attention as functional materials due to their potential application to the development of molecular devices. In this study, introducing sterically hindered substituents onto an anthraquinodimethane (AQD) skeleton allowed researchers to observe the ring-flipping process of the AQD unit and experimentally determine the activation energy of the AQD ring-flip. Researchers from Hokkaido University and ICReDD collaborated to demonstrate based on both experimental and theoretical approaches that the structural change between isomers occurs via the AQD ring-flip process of the molecule. The structure of the intermediate of the ring-flip process was also identified using the AFIR method.

For more information, please refer to the full paper below.

Y. Ishigaki, T. Tadokoro, Y. Harabuchi, Y. Hayashi, S. Maeda, and T. Suzuki. Bulletin of the Chemical Society of Japan. DOI: 10.1246/bcsj.20210355