Photophysical Properties of 4-Dicyanomethylene-2-methyl-6-(p-dimethylamino-styryl)-4H-pyran Revisited: Fluorescence versus Photoisomerization.
DCM dye
fluorescence photoswitching
photochromism
photoisomerization
solvatochromism
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
11 Nov 2020
11 Nov 2020
Historique:
received:
11
06
2020
pubmed:
12
7
2020
medline:
12
7
2020
entrez:
12
7
2020
Statut:
ppublish
Résumé
Although 4-dicyanomethylene-2-methyl-6-(p-dimethylamino-styryl)-4H-pyran (DCM) has been known for many decades as a bright and photostable fluorophore, used for a wide variety of applications in chemistry, biology and physics, only little attention has been paid so far to the presence of multiple isomers and conformers, namely s-trans-(E), s-cis-(E), s-trans-(Z), and s-cis-(Z). In particular, light-induced E-Z isomerization plays a great role on the overall photophysical properties of DCM. Herein, we give a full description of a photoswitchable DCM derivative by a combination of structural, theoretical and spectroscopic methods. The main s-trans-(E) isomer is responsible for most of the fluorescence features, whereas the s-cis-(E) conformer only contributes marginally. The non-emitting Z isomers are generated in large conversion yields upon illumination with visible light (e.g., 485 or 514 nm) and converted back to the E forms by UV irradiation (e.g., 365 nm). Such photoswitching is efficient and reversible, with high fatigue resistance. The E→Z and Z→E photoisomerization quantum yields were determined in different solvents and at different irradiation wavelengths. Interestingly, the fluorescence and photoisomerization properties are strongly influenced by the solvent polarity: the fluorescence is predominant at higher polarity, whereas photoisomerization becomes more efficient at lower polarity. Intermediate medium (THF) represents an optimized situation with a good balance between these two features.
Identifiants
pubmed: 32652655
doi: 10.1002/chem.202002828
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
14341-14350Subventions
Organisme : Agence Nationale de la Recherche
ID : ANR-17-CE07-0056-01
Organisme : European Research Council
ID : grant n. 692981
Pays : International
Informations de copyright
© 2020 Wiley-VCH GmbH.
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