Conjugate Additions When You Least Expect Them

Significance

Polyacenes have been extensively studied due to their potential application in electronic devices, such as organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). Due to decreasing solubility and stability as the acene length increases, peri-substituted polyacenes are often instead the targets for synthetic chemists. Synthesis of soluble and stable forms of these lengthy acenes typically involves the double nucleophilic addition of an organometallic reagent to the corresponding acenequinone, followed by aromatization of the formed diol.