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Diels-Alder Reactions of Organic Semiconductor Surfaces


Nov 13, 2019 - 3:15pm to 4:30pm


PS 111


Jacob W. Ciszek–Loyola University Chicago


The organic semiconductors pentacene and tetracene have an accessible acene core
which readily undergoes Diels-Alder reactions in solution. This same reaction is
readily adaptable to the surface of organic semiconductors, which have been grown
as single crystals for electronic purposes (transistors, photodiode, etc.). Our recent
results allow us to confirm formation of Diels-Alder adducts on the surface of the
organic crystals (XPS, TPD, MS) via a vapor-solid reaction. Various dienophiles
(incorporating a range of reactivity that spans 8 orders of magnitude) have been
successfully reacted. Importantly, the molecular orientation and packing density
within the crystal present avenues for face selectivity reactivity at the surface, and
the reaction itself allows for electronic doping of these crystals post synthesis. This
talk outlines the chemistry, processing requirements, versatility, and our
mechanistic understanding of the Diels-Alder reaction at acene surfaces. It
concludes by discussing our work towards the most likely application in modern
electronic devices including adhesion improvement and band gap engineering.

Event Type: 

Department of Chemistry - Colloquia