Photoswitchable Intramolecular Hydrogen Bonds in 5-Phenylazopyrimidines Revealed By In Situ Irradiation NMR Spectroscopy
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00489319" target="_blank" >RIV/61388963:_____/18:00489319 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/chem.201705146" target="_blank" >http://dx.doi.org/10.1002/chem.201705146</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201705146" target="_blank" >10.1002/chem.201705146</a>
Alternative languages
Result language
angličtina
Original language name
Photoswitchable Intramolecular Hydrogen Bonds in 5-Phenylazopyrimidines Revealed By In Situ Irradiation NMR Spectroscopy
Original language description
NMR spectroscopy with in situ irradiation uncovered unique photoswitchable intramolecular hydrogen bonds (IMHBs) in 5-phenylazopyrimidines with two hydrogen bond donors. These compounds form two stable rotamers, each with one IMHB, and the rotamer ratio changes reversibly upon UV or visible light irradiation. Strong substituent dependence of photoinduced structural changes was observed, using suitable substituents, orthogonal photoswitching can be achieved. For example, whereas UV irradiation caused switching between the two rotamers of the trans isomer of a compound with electron-donating methoxy substituent, visible light enabled to obtain the cis photoisomer. No cis isomer was detected for compounds with electro-neutral or electron-accepting substituents, but photoswitching between the two trans isomers was observed. On the other hand, compounds without hydrogen-bond donors or with one donor only formed stable cis isomers. A mechanism of the photoswitching was proposed by DFT computations.
Czech name
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Czech description
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Classification
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
Result continuities
Project
<a href="/en/project/GA15-11223S" target="_blank" >GA15-11223S: Hydrogen bonds and nuclear quantum delocalisation studied by NMR spectroscopy and theoretical calculations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
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Volume of the periodical
24
Issue of the periodical within the volume
2
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
492-498
UT code for WoS article
000419623600030
EID of the result in the Scopus database
2-s2.0-85037358671