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Three-State Fluorescence of a 2-Functionalized Pyrene-Based RNA Label.

Andreas J Reuss1, Christian Grünewald2, Henrik Gustmann1

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The RNA fluorescence label 2-(2-pyrenylethynyl) adenosine (2PyA) exhibits unique wavelength-dependent fluorescence. This study reveals its emission originates from distinct intramolecular charge transfer states, influenced by excitation energy and molecular configuration.

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Area of Science:

  • Photophysics
  • Molecular Spectroscopy
  • Biophysical Chemistry

Background:

  • RNA structural dynamics are crucial for biological function.
  • Fluorescence labels are essential tools for studying biomolecules.
  • Pyrene-based probes offer unique photophysical properties.

Purpose of the Study:

  • To investigate the unusual wavelength-dependent fluorescence of the pyrene-based RNA label 2-(2-pyrenylethynyl) adenosine (2PyA).
  • To elucidate the excited-state dynamics and emission mechanisms of 2PyA in solution.
  • To correlate fluorescence behavior with molecular structure and excitation conditions.

Main Methods:

  • Steady-state and time-resolved emission spectroscopy.
  • Ultrafast transient absorption spectroscopy.
  • Quantum chemical calculations (CC2 and DFT).

Main Results:

  • 2PyA displays triexponential fluorescence strongly dependent on excitation wavelength.
  • Excitation into the S2 state yields structured, long-lived fluorescence shifted hypsochromically.
  • Emission arises from simultaneous mesomeric (MICT) and twisted (TICT) intramolecular charge transfer states.
  • Populations of these states are influenced by excitation energy, rotational momentum, and molecular geometry (distance and tilt angle).

Conclusions:

  • The complex fluorescence of 2PyA is attributed to simultaneous emission from distinct intramolecular charge transfer states.
  • Excitation wavelength critically controls the population pathways and observed fluorescence characteristics.
  • Molecular geometry, specifically adenine-pyrene distance and tilt, dictates substate stabilization.