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Synthesis of Triptycenemonohydroquinonedibenzoquinone by Comproportionation.

Triptycenetribenzoquinone (BQ)3, where the three benzene rings of triptycene are replaced by 1,4-benzoquinone (BQ) rings, is known to be reduced to triptycenetrihydroquinone (HQ)3. In contrast, a molecule where both BQ and HQ moieties coexist in a triptycene framework has never been reported. In this study, triptycenemonohydroquinonedibenzoquinone ((HQ)1(BQ)2) in which one HQ unit and two BQ units coexist was generated by comproportionation between (BQ)3 and (HQ)3 and isolated by recrystallization. We obtained two types of crystals with different hydrogen-bonding structures by changing the cosolvents.