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Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
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Intermolecular Interactions in Crystals Modulate Intramolecular Excited State Proton Transfer Reactions.

Hyein Hwang1,2,3, Alasdair Mackenzie4, Michał Andrzej Kochman5,6

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|July 28, 2025
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Summary
This summary is machine-generated.

Crystal packing significantly impacts excited state intramolecular proton transfer (ESIPT) dynamics in dihydroxyanthraquinone (DHAQ) isomers. Intermolecular hydrogen bonding in crystals alters proton transfer pathways compared to solutions.

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Area of Science:

  • Photochemistry
  • Solid-state chemistry
  • Supramolecular chemistry

Background:

  • Proton transfer is vital in chemical and biological systems.
  • Excited state intramolecular proton transfer (ESIPT) is key for photostability in hydroxyanthraquinone pigments.
  • The surrounding environment critically influences proton transfer dynamics.

Purpose of the Study:

  • Investigate how crystalline packing affects photoinduced proton transfer dynamics in dihydroxyanthraquinone (DHAQ) isomers.
  • Compare proton transfer in crystalline versus solution phases for DHAQ isomers.
  • Understand the role of intermolecular interactions in modulating ESIPT.

Main Methods:

  • Studied ESIPT dynamics in single crystals of DHAQ constitutional isomers.
  • Compared proton transfer behavior in crystalline and solution phases.
  • Analyzed the influence of crystal packing and intermolecular hydrogen bonding on excitonic couplings and reaction pathways.

Main Results:

  • Substantial differences in proton transfer dynamics were observed between crystalline and solution phases for 1,4- and 1,5-DHAQ isomers.
  • Intermolecular hydrogen bonding in 1,4- and 1,5-DHAQ crystals led to larger excitonic couplings, altering reaction pathways.
  • 1,8-DHAQ showed minimal changes, lacking intermolecular hydrogen bonds in the crystal.
  • An ESIPT relaxation channel, absent in solution, emerged in the 1,4-DHAQ crystal due to intermolecular interactions.

Conclusions:

  • Crystal packing plays a critical role in modulating proton transfer dynamics.
  • Molecular packing can be strategically controlled to optimize reaction pathways in solid-state environments.
  • Findings provide insights into designing materials with tailored photophysical properties based on crystal structure.