Successful ring-opening of propeller-shaped molecular triptycene by acid!

Expected as a new synthesis method for acenes used in organic semiconductors, etc.

By simply mixing acid with triptycene, a propeller-shaped molecule with three blades of benzene rings, he discovered a reaction that removes only one of the three seams of the blades, and he successfully applied this reaction to the synthesis of acenes.

The University has also issued a press release.

Abstract

The triptycene scaffold has been ring-opened by using a retro-Friedel-Crafts-type reaction under acidic conditions to give its corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. In addition, the reaction has been successfully applied toward the synthesis of tetracene.