Abstract
The relative photoreactivities of several bridge-ring systems 2–4 have been studied. Compound 3 is photoreactive whereas 2 and 4 are photoinert when irradiated with 254 nm light. The systems contain aromatic electron donors and halogen electron acceptors which are held at well-defined geometries that vary in the degree of rigidity at the electron acceptor termini. The relative photoreactivities in the photoinduced intramolecular electron transfer processes cannot be explained by calculated relative free-energy or rate constant values for electron transfer. The discrepancies between the relative experimental photo-reactivities and those predicted based on calculated values of free energy (Weller equation) are rationalized by a rigidity argument.
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