Design, Synthesis, and Properties of Redox-Active Bisquinodimethanes

This book focuses on the construction of redox systems composed of doubly fused para-quinodimethane (p-QD) units and on the elucidation of the unique redox behavior. p-QD is a class of non-aromatic -conjugated compounds that is well-known to be interconvertible scaffolds in many response systems due to its contribution of resonance structure with a planar aromatic sextet ring. This book describes studies on a strategy for precisely controlling the frontier orbital levels of p-QD-based redox systems and a nature of cationic states of -electron systems with doubly fused p-QD units. The author revealed that multi-redox unimolecular systems with cross-linking of the two sterically strained p-QD units exhibit unique hysteretic character or have a domino effect upon electron transfer, which cannot be achieved in a monomeric p-QD-based system. Thus, these studies are milestones in creating functional redox systems unprecedented dynamic redox (dyrex) behaviors. A study on cationic states of -electron systems with doubly fused p-QD units and their intrinsic redox properties will lead to the development of unprecedented dyrex systems, the frontier orbital levels of which can be precisely controlled by input of external stimuli such as electric potential and heat. This book benefits chemists with a deeper understanding of the redox-active molecules.

Nominated as an outstanding Ph.D. thesis by Hokkaido University Provides a comprehensive introduction to redox-active -conjugated system Contains structural and electronic properties of bisquinodimethanes

Autorentext

Takashi Harimoto was born in Yokohama, Kanagawa Prefecture, Japan, in 1997. He graduated from Hokkaido University in 2020 and received his Ph.D. in 2024 under the supervision of Professor Takanori Suzuki. He started his academic career as an assistant professor at Institute for Molecular Science in 2024. His research interest is focusing not only on redox-active molecules but also on unique chemical phenomena in 3D assembly of organic -conjugated systems through experimental and theoretical studies.

Inhalt

1. General Introduction.- 2. Enhancement of NIR-Absorbing Ability of Bis(diarylmethylium)-Type Dicationic Dyes Based on an Ortho-Substitution Strategy.- 3. Octaarylated Bisquinodimethanes: Double Dynamic Redox Systems Enabling the Control of [n]Acene Structure and NIR Absorptions.- 4. Domino-Redox Reaction Induced by a Conformational Change Based on Dithiin Bisquinodimethane Skeleton.