Domino‐Redox Reaction Induced by An Electrochemically Triggered Conformational Change.

Autor: Harimoto, Takashi, Tadokoro, Tomoki, Sugiyama, Soichiro, Suzuki, Takanori, Ishigaki, Yusuke
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Zdroj: Angewandte Chemie; 1/2/2024, Vol. 136 Issue 1, p1-7, 7p
Abstrakt: The concept of a domino‐type reaction has been applied in a wide range of fields such as synthetic organic chemistry, material engineering, and life science. To extend the domino concept to redox chemistry, we designed and synthesized a dimeric quinodimethane (QD) with a nonplanar dithiin spacer. The domino‐redox properties can be activated by raising the temperature, based on a thermally equilibrated twisted conformation of QD, which has a higher HOMO level that is more readily oxidized. After one QD unit is oxidized (trigger), steric repulsion and electronic interaction between electrophores make the neighboring QD unit adopt a twisted conformation (domino process), which facilitates the following oxidation. Thus, a domino‐redox reaction was achieved for the first time by a change in the HOMO level due to a drastic change in the molecular conformation. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index