Intramolecular triplet energy transfer has been studied in bichromophoric molecules that incorporate an anthracene donor and ketone or alkene accepters connected by two rigid, bicyclic saturated hydrocarbon units. Two-laser excitation of the anthracene group results in production of the T-2 State which subsequently undergoes energy transfer to the accepters (k approximate to 10(10) s(-1)), as indicated by depletion of the T-T absorption. In 1, decay of the acceptor (ketone) triplet state involves a competition between ring opening and back energy transfer to the anthracene T-1 state. In 2-4, rotation of the alkene triplets to perpendicular geometries relieves ring strain in the bicyclic connecting units, thus providing a barrier to back energy transfer. A fraction of the twisted triplets relaxes to the ground state without irreversible chemistry.