TY  - JOUR
A1  - Klimek, Robin
A1  - Asido, Marvin
A1  - Hermanns, Volker
A1  - Junek, Stephan
A1  - Wachtveitl, Josef
A1  - Heckel, Alexander
T1  - Inactivation of competitive decay channels leads to enhanced coumarin photochemistry
T2  - Chemistry – a European journal
N2  - In the development of photolabile protecting groups, it is of high interest to selectively modify photochemical properties with structural changes as simple as possible. In this work, knowledge of fluorophore optimization was adopted and used to design new coumarin- based photocages. Photolysis efficiency was selectively modulated by inactivating competitive decay channels, such as twisted intramolecular charge transfer (TICT) or hydrogen-bonding, and the photolytic release of the neurotransmitter serotonin was demonstrated. Structural modifications inspired by the fluorophore ATTO 390 led to a significant increase in the uncaging cross section that can be further improved by the simple addition of a double bond. Ultrafast transient absorption spectroscopy gave insights into the underlying solvent-dependent photophysical dynamics. The chromophores presented here are excellently suited as new photocages in the visible wavelength range due to their simple synthesis and their superior photochemical properties.
KW  - ATTO 390
KW  - coumarin
KW  - fluorophore
KW  - photocage
KW  - TICT
Y1  - 2022
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/79099
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-790998
SN  - 1521-3765
N1  - We gratefully acknowledge funding of the Deutsche Forschungsgemeinschaft (DFG) through the research training group ‘‘CLiC’’ (GRK 1986, Complex Light-Control) and the CRC902 “Molecular principles of RNA-based regulation”. Open Access funding enabled and organized by Projekt DEAL.
VL  - 28
IS  - 35, art. e202200647
SP  - 1
EP  - 8
PB  - Wiley-VCH
CY  - Weinheim
ER  -