Control over excited state intramolecular proton transfer and photoinduced tautomerization: Influence of the hydrogen-bond geometry

Giovanny A. Parada, Todd F. Markle, Starla D. Glover, Leif Hammarström, Sascha Ott, Burkhard Zietz

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

The influence of H-bond geometry on the dynamics of excited state intramolecular proton transfer (ESIPT) and photoinduced tautomerization in a series of phenol-quinoline compounds is investigated. Control over the proton donor-acceptor distance (dDA) and dihedral angle between the proton donor-acceptor subunits is achieved by introducing methylene backbone straps of increasing lengths to link the phenol and quinoline. We demonstrate that a long dDA correlates with a higher barrier for ESIPT, while a large dihedral angle opens highly efficient deactivation channels after ESIPT, preventing the formation of the fully relaxed tautomer photoproduct.

Original languageEnglish
Pages (from-to)6362-6366
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number17
DOIs
Publication statusPublished - Apr 20 2015

Keywords

  • excited state
  • fluorescence
  • hydrogen bonds
  • intramolecular proton transfer
  • phenols
  • tautomerism

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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