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 language | English |
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Pages (from-to) | 6362-6366 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 21 |
Issue number | 17 |
DOIs | |
Publication status | Published - Apr 20 2015 |
Keywords
- excited state
- fluorescence
- hydrogen bonds
- intramolecular proton transfer
- phenols
- tautomerism
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry