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Self-assembly of sensitizer and acceptor molecules has recently emerged as a promising strategy to facilitate and harness photon upconversion via triplet–triplet annihilation (TTA-UC). In addition to the energetic requirements, the structure and relative orientation of these molecules can have a strong influence on TTA-UC rates and efficiency. Here we report the synthesis of five different acceptor molecules composed of an anthracene core functionalized with 9,10- or 2,6-phenyl, methyl, or directly bound phosphonic acid groups and their incorporation into self-assembled bilayers on a ZrO 2 surface. All five films facilitate green-to-blue photon upconversion with Φ uc as high as 0.0023. The efficiency of TTA, and not triplet energy transfer, fluorescence, or losses via FRET, was primarily responsible for dictating the Φ uc emission. Even for molecules having similar photophysical properties, variation in the position of the phosphonic acid resulted in dramatically different Φ TTA , I th values, γ TTA , and D . Interestingly, we observed a strong linear correlation between Φ TTA and the I th value but the cause of this relationship, if any, is unclear.