Phenazine-1,6-dicarboxamides: Redox-Responsive Molecular Switches

We introduce phenazine-1,6-dicarboxamides as redox-responsive molecular switches. The reduction of their phenazine core transforms them from hydrogen-bond acceptors into hydrogen-bond donors and thus forces the secondary amide substituents to turn around. The resulting conformational changes are envisioned to form the basis for butterfly coil foldamers undergoing reversible extension and contraction in response to changing their oxidation state.本研究将吩嗪-1,6-二甲酰胺（phenazine-1,6-dicarboxamides）作为氧化还原响应型分子开关（redox-responsive molecular switches）。该类化合物的吩嗪母核（phenazine core）经还原反应后，可从氢键受体（hydrogen-bond acceptors）转变为氢键供体（hydrogen-bond donors），进而迫使仲酰胺取代基（secondary amide substituents）发生扭转。由此产生的构象变化，有望作为蝶形卷曲折叠体（butterfly coil foldamers）的结构基础，使其可随自身氧化态的变化发生可逆的伸展与收缩。