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

30 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

Fingerprint

Proton transfer
Excited states
Hydrogen bonds
Dihedral angle
Phenol
Phenols
Geometry
Protons
quinoline

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Control over excited state intramolecular proton transfer and photoinduced tautomerization : Influence of the hydrogen-bond geometry. / Parada, Giovanny A.; Markle, Todd F.; Glover, Starla D.; Hammarström, Leif; Ott, Sascha; Zietz, Burkhard.

In: Chemistry - A European Journal, Vol. 21, No. 17, 20.04.2015, p. 6362-6366.

Research output: Contribution to journalArticle

Parada, Giovanny A. ; Markle, Todd F. ; Glover, Starla D. ; Hammarström, Leif ; Ott, Sascha ; Zietz, Burkhard. / Control over excited state intramolecular proton transfer and photoinduced tautomerization : Influence of the hydrogen-bond geometry. In: Chemistry - A European Journal. 2015 ; Vol. 21, No. 17. pp. 6362-6366.
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