Bis(azoliums) are readily available in one step from cyclic (alkyl)(amino)carbenes and bis(acyl chlorides). A two-electron reduction of the bis(azolium), featuring a gem-(dimethyl)malonoyl spacer, leads to the corresponding transient diradical, which undergoes an intramolecular cyclization. The latter can be re-oxidized at a higher potential to yield back the bis(azolium). The redox bistability of this simple organic molecular system is linked to the formation of a weak C–O bond (27 kcal mol⁻¹). Both redox forms can be isolated and stored for months without evidence of decay.

中文翻译：

---

偶然发现了衍生自环状（烷基）（氨基）卡宾的氧化还原双稳态分子†

在一个步骤中，双（azo）很容易从环状（烷基）（氨基）卡宾和双（酰氯）中获得。以宝石-（二甲基）丙二酰基间隔基为特征的双（偶氮）的双电子还原导致相应的瞬态双自由基，其经历分子内环化。后者可以在较高电势下被重新氧化，以产生双（偶氮）。这种简单的有机分子系统的氧化还原双稳态性与弱C–O键（27 kcal mol ^-1）的形成有关。两种氧化还原形式都可以分离并保存数月，而没有衰减的迹象。