Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F13%3A50001296" target="_blank" >RIV/62690094:18470/13:50001296 - isvavai.cz</a>
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S014372081300137X" target="_blank" >http://www.sciencedirect.com/science/article/pii/S014372081300137X</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.dyepig.2013.04.010" target="_blank" >10.1016/j.dyepig.2013.04.010</a>

Result language
angličtina
Original language name
Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues
Original language description
Three N-analogues of Pechmann dye with identical aryl groups in the 5, 50-positions (aryl Ľ phenyl, 2-naphthyl, 2-thienyl) and carboxy ester groups in the 3,30-positions were synthesized by oxidative dimerization of the corresponding 5-aryl-pyrrolinone esters. Derivatives with improved solubility in most organic solvents were prepared by subsequent N-methylation. The dyes were confirmed as E isomers, i.e. holding an all-trans 1,6-diaryl-1,3,5-hexatriene backbone, with slight torsion of central C]C bondby X-ray diffraction and density functional theory (DFT) calculations. No E/Z photoisomerization was observed. Full assignment of 1H and 13C NMR signals was performed. The absorption spectra are quite similar with the maxima in the range 572 nm (aryl Ľ phenyl)e643 nm (aryl Ľ 2-thienyl) in accordance with time dependent DFT calculations of excitation energies. No fluorescence was observed in solution, while all compounds fluoresce in low temperature solvent glass (77 K) and a weak solid-s
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CF - Physical chemistry and theoretical chemistry
OECD FORD branch
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Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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