The large thermodynamic stabilization (�aromaticity�) of aromatic hydrocarbons provides them with a certain level of protection from any chemical reactions that would cause disruption, even just temporarily, to the cyclic delocalization of electrons in their conjugated pi-systems. As polycyclic aromatic hydrocarbons become larger, however, many bay region Diels-Alder cycloadditions become progressively easier, because progressively greater fractions of the aromaticity are preserved in the initial adducts. We are attempting to exploit this reactivity to synthesize graphene nanoribbons (figure below), inter alia.

Diels-Alder cycloadditions in the bay regions of large polycyclic aromatic hydrocarbons

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.