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Control over Excited State Intramolecular Proton Transfer and Photoinduced Tautomerization: Influence of the Hydrogen‐Bond Geometry
Author(s) -
Parada Giovanny A.,
Markle Todd F.,
Glover Starla D.,
Hammarström Leif,
Ott Sascha,
Zietz Burkhard
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500244
Subject(s) - tautomer , dihedral angle , intramolecular force , chemistry , hydrogen bond , proton , photochemistry , quinoline , methylene , excited state , molecular geometry , bond length , acceptor , molecule , crystallography , crystal structure , stereochemistry , organic chemistry , atomic physics , physics , quantum mechanics , condensed matter physics
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 ( d DA ) 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 d DA 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.