Published March 25, 2019 | Version Accepted Manuscript

Persistent solid-state phosphorescence and delayed fluorescenceat room temperature from a twisted hydrocarbon

  • 1. Universidade Federal de Santa Catarina 88040-900 Florianópolis, SC, Brazil
  • 2. Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115, av. Schweitzer, 33600 Pessac, France

Description

The dehydrating cyclotrimerization of 1-tetralone in the presence of titanium tetrachloride at high temperature leads to homotruxene, a nonplanararene 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%, cleanly visible to the human eye after switch-off of excitation. Triplet-triplet annihilation is found to simultaneously lead to an intense delayed fluorescence, unprecedented from a pure hydrocarbon at ambient conditions, with a lifetime of 0.11 s.

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Salla Bock RTP+DF from a hydrocarbon HAL.pdf

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Additional details

Funding

European Commission
OCTA - Organic Charge Transfer Applications 778158