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We have studied the phenomenon of photon upconversion in systems of two model compounds as highly efficient blue emitters sensitized with metallated macrocycle molecules in thin films. The bimolecular upconversion process in these systems is based on the presence of a metastable triplet excited state of the macrocycles giving rise to dramatically different photophysical characteristics relative to the other known methods for photon upconversion such as two-photon absorption, parametric processes, second harmonic generation, and sequential multiphoton absorption. The chosen blue emitter molecules have suitably positioned triplet levels: in the case of an oligofluorine—essentially higher and in the case of diphenylanthracene—lower than the sensitizer porphyrin platinum triplet level and thus two excitation pathways for photon upconversion were observed and investigated.