Porphyrin–Anthracene Complexes: Potential in Triplet–Triplet Annihilation Upconversion

Triplet–triplet annihilation photon upconversion (TTA-UC) systems contain both an absorbing and an emitting molecule, the sensitizer and annihilator, respectively. Through a series of energy-transfer steps, two low frequency photons can be combined into one high frequency photon. In organic solvents, the required energy transfer steps are limited by diffusion and are relatively efficient. In solid-state systems, however, the diffusion is slower, which usually results in lower efficiencies for these systems. An interesting way around this is to connect the sensitizer and annihilator. In order to increase understanding of the TTA-UC process in supramolecular systems, we synthesized four pyridine-substituted anthracene annihilators capable of coordinating axially to a zinc octaethylporphyrin sensitizer with a maximum binding constant of 6000 M–1 in toluene. This is a first example of a sensitizer–annihilator coordination complex for TTA-UC. Both the upconversion efficiency and the parasitic quenching of exci...