Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues

Popis výsledku anglicky

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

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CF - Fyzikální chemie a teoretická chemie

OECD FORD obor

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Projekt

—

Návaznosti

N - Vyzkumna aktivita podporovana z neverejnych zdroju

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Dyes and pigments

ISSN

0143-7208

e-ISSN

—

Svazek periodika

98

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

10

Strana od-do

530-539

Kód UT WoS článku

000321169000029

EID výsledku v databázi Scopus

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