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Fluorescent Liquid Tetrazines.

Maximilian Paradiz Dominguez1, Begüm Demirkurt1, Marion Grzelka2

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Summary
This summary is machine-generated.

Branched alkoxy tetrazines are fluorescent liquids. Their fluorescence quantum yields are higher for 3-chloro-6-alkoxytetrazines due to slower intersystem crossing, influenced by substituent size and electronic properties.

Keywords:
excited statesfluorescenceinter system crossingrheologyviscosity

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Area of Science:

  • Organic Chemistry
  • Photophysics
  • Materials Science

Background:

  • Tetrazines are known for their fluorescence.
  • Branched alkoxy substituents render tetrazines liquid at ambient temperatures.
  • High chromophore density is maintained in these liquid tetrazines.

Purpose of the Study:

  • Investigate photophysical properties of alkoxy-tetrazines in solution and neat liquids.
  • Correlate alkoxy substituent size with liquid viscosity.
  • Understand factors influencing fluorescence quantum yields and decay pathways.

Main Methods:

  • Time-resolved spectroscopy to study decay pathways.
  • Quantum chemical calculations to probe electronic states and energy barriers.
  • Femtosecond time-resolved anisotropy studies in solution and neat liquids.

Main Results:

  • 3-chloro-6-alkoxytetrazines exhibit higher fluorescence quantum yields than 3,6-dialkoxy derivatives.
  • Intersystem crossing is a significant decay pathway, faster in 3,6-dialkoxy tetrazines.
  • Alkoxy chain length positively correlates with rotational correlation times in solution.
  • Fast anisotropy decay in neat liquids indicates efficient exciton migration.

Conclusions:

  • The difference in intersystem crossing rates is attributed to the activation energy for tetrazine core distortion and subsequent state crossing.
  • Efficient intersystem crossing in 3,6-dialkoxy tetrazines competes with fluorescence.
  • Exciton migration is rapid in neat liquid films of alkoxy-tetrazines.