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 |
|---|---|
| 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 |
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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 journal › Article
}
TY - JOUR
T1 - Control over excited state intramolecular proton transfer and photoinduced tautomerization
T2 - Influence of the hydrogen-bond geometry
AU - Parada, Giovanny A.
AU - Markle, Todd F.
AU - Glover, Starla D.
AU - Hammarström, Leif
AU - Ott, Sascha
AU - Zietz, Burkhard
PY - 2015/4/20
Y1 - 2015/4/20
N2 - 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.
AB - 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.
KW - excited state
KW - fluorescence
KW - hydrogen bonds
KW - intramolecular proton transfer
KW - phenols
KW - tautomerism
UR - http://www.scopus.com/inward/record.url?scp=84926628463&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84926628463&partnerID=8YFLogxK
U2 - 10.1002/chem.201500244
DO - 10.1002/chem.201500244
M3 - Article
VL - 21
SP - 6362
EP - 6366
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 17
ER -