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Persistent Solid-State Phosphorescence and Delayed Fluorescence at Room Temperature by a Twisted Hydrocarbon.

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Homotruxene, a nonplanar arene, exhibits room-temperature phosphorescence and delayed fluorescence in air. This pure hydrocarbon

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cyclotrimerizationdelayed fluorescenceroom-temperature phosphorescencespin-orbit couplingtriplet-triplet annihilation

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Area of Science:

  • Organic Chemistry
  • Materials Science

Background:

  • Nonplanar arenes are of interest for their unique photophysical properties.
  • Achieving room-temperature phosphorescence in pure hydrocarbons under ambient conditions is challenging.

Purpose of the Study:

  • To synthesize and characterize homotruxene.
  • To investigate the photophysical properties of homotruxene, including phosphorescence and delayed fluorescence.

Main Methods:

  • Dehydrating cyclotrimerization of 1-tetralone using titanium tetrachloride at high temperatures.
  • Spectroscopic analysis to determine photophysical properties such as phosphorescence lifetime and quantum yield.

Main Results:

  • Successful synthesis of homotruxene, a nonplanar arene with ethylene bridges.
  • Observation of room-temperature phosphorescence in air with a lifetime of 0.38 s and quantum yield of 5.6%.
  • Detection of substantial delayed fluorescence via triplet-triplet annihilation, with a lifetime of 0.11 s.

Conclusions:

  • The nonplanar structure of homotruxene facilitates pronounced spin-orbit coupling and high triplet energy.
  • Homotruxene demonstrates efficient room-temperature phosphorescence and delayed fluorescence, making it a promising material for optoelectronic applications.