Antiaromatic hydrocarbon boasts unusual stability

Structure

Source: © Ulrich Hintermair/University of Bath

Pentalene-based system can reversibly switch between aromatic and antiaromatic states without undergoing skeletal or conformational changes

A rare example of an antiaromatic hydrocarbon that’s stable at room temperature has been made using a straightforward and completely reversible oxidation reaction. While annelation with other π systems is the most common way to stabilise an antiaromatic structure, 1,3,4,6-tetraphenylpentalene’s (Ph4Pn) stability appears to come from the steric bulk of its phenyl substituents.