Theoretical calculations have shown acenes and more specifically aza-acenes as attractive materials for organic semiconductors (Houk et al JACS, 2007 , 129, 1805). Interest in aza-acenes for n-type materials has increased substantially over the past few years. However realization of new derivatives has been severely hindered by current synthetic approaches. New synthetic strategies will be presented which have allowed for the first time new diaza-tetracene and diaza-pentacene derivatives. The HOMO and LUMO energy levels of these materials are tunable through appropriate substitution and as predicted deepened (DFT Calculations). For example, determination of the LUMO energy levels by cyclic voltammetry for a dichlorodiazatetracene (-1.5 V vs ferrocene) shows that these materials are in the range of common fullerene acceptors (e.g. C60). The photophysical and electrochemical characterization of these materials will be presented along with the photovoltaic performance.

Novel aza-acenes towards new n-type materials

243rd National Meeting (2012)

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