4-OH coumarin based rotary switches: Tautomeric state and effect of the stator
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F21%3APU141894" target="_blank" >RIV/00216305:26310/21:PU141894 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0143720820315588?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0143720820315588?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.dyepig.2020.108861" target="_blank" >10.1016/j.dyepig.2020.108861</a>
Alternative languages
Result language
angličtina
Original language name
4-OH coumarin based rotary switches: Tautomeric state and effect of the stator
Original language description
Two new 4-OH coumarin based rotary switches, containing fixed carbonyl groups in the rotor, have been synthesized and their properties have been studied by combined use of DFT calculations and molecular spectroscopy (UV-Vis absorbance and emission, NMR). It was found that the structure of the stator (naphthyl in 2 or quinolyl moiety in 3) and solvents polarity do not influence their azo-hydrazone tautomerism. Both compounds exist as keto (hydrazone) tautomers. The NMR data indicate a mixture of E (major) and Z (minor) keto form isomers in solution. The results are in very good agreement with ground state DFT calculations. The keto tautomers exhibit different emission behavior depending on the structure of the stators. Comparing to 2, more intensive emission and higher lifetime was observed in 3, where the formation of intramolecular hydrogen bonding of the hydrazone NH with the N atom of quinoline restricts the rotation of the stator. According to the spectral data and the TDDFT analysis the observed emission originates from the excitation of the keto tautomers and does not include excited state proton transfer. It was shown that the protonation is a suitable stimulus for E/Z switching in 2, where a possible mechanism is sketched. In the case of 3, the addition of acid leads to the pmtonation of the quinolyl nitrogen atom, which slightly affects the E/Z isomerization ratio.
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/GA17-21105S" target="_blank" >GA17-21105S: Multi-photon absorbing Materials FOR 3D fabrication and 3D imaging (M-FOR-3D)</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
DYES AND PIGMENTS
ISSN
0143-7208
e-ISSN
1873-3743
Volume of the periodical
184
Issue of the periodical within the volume
108861
Country of publishing house
GB - UNITED KINGDOM
Number of pages
12
Pages from-to
1-12
UT code for WoS article
000580897700102
EID of the result in the Scopus database
2-s2.0-85091665153