Inactivation of competitive decay channels leads to enhanced coumarin photochemistry
- 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.
Author: | Robin KlimekGND, Marvin AsidoORCiDGND, Volker HermannsGND, Stephan JunekGND, Josef WachtveitlORCiDGND, Alexander HeckelORCiDGND |
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URN: | urn:nbn:de:hebis:30:3-790998 |
DOI: | https://doi.org/10.1002/chem.202200647 |
ISSN: | 1521-3765 |
Parent Title (English): | Chemistry – a European journal |
Publisher: | Wiley-VCH |
Place of publication: | Weinheim |
Document Type: | Article |
Language: | English |
Date of Publication (online): | 2022/04/14 |
Date of first Publication: | 2022/04/14 |
Publishing Institution: | Universitätsbibliothek Johann Christian Senckenberg |
Release Date: | 2023/10/18 |
Tag: | ATTO 390; TICT; coumarin; fluorophore; photocage |
Volume: | 28 |
Issue: | 35, art. e202200647 |
Article Number: | e202200647 |
Page Number: | 8 |
First Page: | 1 |
Last Page: | 8 |
Note: | 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. |
HeBIS-PPN: | 516371029 |
Institutes: | Biochemie, Chemie und Pharmazie |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Sammlungen: | Universitätspublikationen |
Licence (German): | Creative Commons - CC BY - Namensnennung 4.0 International |