The dehydrating cyclotrimerization of 1-tetralone in the presence of titanium tetrachloride at high temperatures leads to homotruxene, a nonplanar arene in which the twist angles between its three outer benzene rings and the central benzene are stabilized by ethylene bridges. This non-planar configuration allows for pronounced spin-orbit coupling and a high triplet energy, leading to room-temperature phosphorescence in air with a lifetime of 0.38 s and a quantum yield of 5.6 %, clearly visible to the human eye after switching off the excitation. Triplet-triplet annihilation is found to simultaneously lead to a substantial delayed fluorescence, unprecedented from a pure hydrocarbon at ambient conditions, with a lifetime of 0.11 s.
Keywords: cyclotrimerization; delayed fluorescence; room-temperature phosphorescence; spin-orbit coupling; triplet-triplet annihilation.
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