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Symmetry breaking charge separations have been found to be important for charge transfer in bacteriochlorophyll pairs in photosynthetic reaction centers, but engineering symmetry breaking charge separations in artificial dimers of related chromophores is challenging. Here, the authors report the design and synthesis of aromatic-bridged as well as meso-meso-linked BF2-smaragdyrin dimers that exhibit symmetry-breaking charge transfer properties.