- Treffer 1 von 1
Towards low-energy-light-driven bistable photoswitches
- Thermally stable photoswitches that are driven with low-energy light are rare, yet crucial for extending the applicability of photoresponsive molecules and materials towards, e.g., living systems. Combined ortho-fluorination and -amination couples high visible light absorptivity of o-aminoazobenzenes with the extraordinary bistability of o-fluoroazobenzenes. Herein, we report a library of easily accessible o-aminofluoroazobenzenes and establish structure-property relationships regarding spectral qualities, visible light isomerization efficiency and thermal stability of the cis-isomer with respect to the degree of o-substitution and choice of amino substituent. We rationalize the experimental results with quantum chemical calculations, revealing the nature of low-lying excited states and providing insight into thermal isomerization. The synthesized azobenzenes absorb at up to 600 nm and their thermal cis-lifetimes range from milliseconds to months. The most unique example can be driven from trans to cis with any wavelength from UV upThermally stable photoswitches that are driven with low-energy light are rare, yet crucial for extending the applicability of photoresponsive molecules and materials towards, e.g., living systems. Combined ortho-fluorination and -amination couples high visible light absorptivity of o-aminoazobenzenes with the extraordinary bistability of o-fluoroazobenzenes. Herein, we report a library of easily accessible o-aminofluoroazobenzenes and establish structure-property relationships regarding spectral qualities, visible light isomerization efficiency and thermal stability of the cis-isomer with respect to the degree of o-substitution and choice of amino substituent. We rationalize the experimental results with quantum chemical calculations, revealing the nature of low-lying excited states and providing insight into thermal isomerization. The synthesized azobenzenes absorb at up to 600 nm and their thermal cis-lifetimes range from milliseconds to months. The most unique example can be driven from trans to cis with any wavelength from UV up to 595 nm, while still exhibiting a thermal cis-lifetime of 81 days. <br /> [GRAPHICS] <br /> .…
Verfasserangaben: | Kim Kuntze, Jani Viljakka, Evgenii TitovORCiDGND, Zafar AhmedORCiDGND, Elina KaleniusORCiD, Peter SaalfrankORCiDGND, Arri PriimagiORCiD |
---|---|
DOI: | https://doi.org/10.1007/s43630-021-00145-4 |
ISSN: | 1474-905X |
ISSN: | 1474-9092 |
Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/34888753 |
Titel des übergeordneten Werks (Englisch): | Photochemical & photobiological sciences / European Society for Photobiology |
Untertitel (Englisch): | ortho-fluoroaminoazobenzenes |
Verlag: | Springer |
Verlagsort: | Heidelberg |
Publikationstyp: | Wissenschaftlicher Artikel |
Sprache: | Englisch |
Datum der Erstveröffentlichung: | 10.12.2022 |
Erscheinungsjahr: | 2022 |
Datum der Freischaltung: | 12.04.2024 |
Band: | 21 |
Ausgabe: | 2 |
Seitenanzahl: | 15 |
Erste Seite: | 159 |
Letzte Seite: | 173 |
Fördernde Institution: | H2020 European Research Council [679646]; Luonnontieteiden ja Tekniikan Tutkimuksen Toimikunta [321065]; Graduate School, Tampere University; Deutsche ForschungsgemeinschaftGerman Research Foundation (DFG) [454020933] |
Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC-Klassifikation: | 5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie |
6 Technik, Medizin, angewandte Wissenschaften / 62 Ingenieurwissenschaften / 620 Ingenieurwissenschaften und zugeordnete Tätigkeiten | |
Peer Review: | Referiert |
Publikationsweg: | Open Access / Hybrid Open-Access |
Lizenz (Deutsch): | CC-BY - Namensnennung 4.0 International |