Photoswitching Behavior of 5-Phenylazopyrimidines: In Situ Irradiation NMR and Optical Spectroscopy Combined with Theoretical Methods

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00490912" target="_blank" >RIV/61388963:_____/18:00490912 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/acs.joc.8b00569" target="_blank" >http://dx.doi.org/10.1021/acs.joc.8b00569</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.8b00569" target="_blank" >10.1021/acs.joc.8b00569</a>

Result language
angličtina
Original language name
Photoswitching Behavior of 5-Phenylazopyrimidines: In Situ Irradiation NMR and Optical Spectroscopy Combined with Theoretical Methods
Original language description
The photoswitching behavior of 5-phenylazopyrimidines was investigated by optical methods and NMR spectroscopy with in situ irradiation sustained by mathematical modeling and DFT calculations. Irradiation of various compounds with electron-donating groups on the pyrimidine ring and substituents with electron-withdrawing as well as electron-donating substituent in the para-position of the phenyl ring were examined. All compounds could be successfully converted to the cis isomer, this isomerization and the subsequent thermal fading were studied. Switching cycles can be repeated without signs of photodegradation for most of the compounds, which makes them adept to molecular photoswitches. Interestingly, the chloro and cyano derivatives can be switched without UV light, which makes them vis(pi -> pi) vis(n -> pi*) photoswitches. Surprisingly equal trans-to-cis photoisomerization quantum yields for pi -> pi* and n -> pi* excitation indicate the blocking of the inversion pathway following pi -> pi* excitation. In contrast to that, DFT computations suggest the inversion mechanism for the reverse thermal cis-to-trans isomerization of 5-phenylazopyrimidines.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry

Project
<a href="/en/project/GA18-11851S" target="_blank" >GA18-11851S: Intermolecular interactions studied by NMR spectroscopy and advanced quantum-chemical calculations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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