Electron and energy transfer reactions in covalently connected donor-bridge-acceptor assemblies are strongly dependent, not only on the donor-acceptor distance, but also on the electronic structure of the bridge. In this article we describe some well characterised systems where the bridges are pi-conjugated chromophores, and where, specifically, the interplay between bridge length and energy plays an important role for the donor-acceptor electronic coupling. For any application that relies on the transport of electrons, for example molecule based solar cells or molecular scale electronics, it will be imperative to predict the electron transfer capabilities of different molecular structures. The potential difficulties with making such predictions and the lack of suitable models are also discussed.