Interplay of electronic and steric effects controls the regiochemistry of addition of dienophiles to linear polyacenes. In general, the Diels-Alder (DA) addition of N-alkylmaleimides to derivatives of anthracene, tetracene and pentacene occurs at the central aromatic ring. However, substitution at that position with a bulky/electroactive substituent causes the reaction to take place at a peripheral location, resulting in both kinetic and thermodynamic control. A series of DA adducts with electronically interesting polyacenes (figure) for potentially useful electronic applications will be presented.

Regiochemical control in Diels-Alder reaction of linear polyacenes

245th National Meeting (2013)

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