Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanolgues

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F13%3A39896178" target="_blank" >RIV/00216275:25310/13:39896178 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.dyepig.2013.04.010" target="_blank" >http://dx.doi.org/10.1016/j.dyepig.2013.04.010</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 heteroanolgues

Popis výsledku v původním jazyce

Three N-analogues of Pechmann dye with identical aryl groups in the 5, 5'-positions (aryl=phenyl, 2-naphthyl, 2-thienyl) and carboxy ester groups in the 3,3'-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 confrmed as E isomers, i.e. holding an all-trans 1,6-diaryl-1,3,5-hexatriene backbone, with slight torsion of central C=C bond byX-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= phenyl)-643 nm (aryl = 2-thienyl) in accordance with time dependent DFTcalculations of excitation energies. No fluorescence was observed in solution, while all compounds fluoresce in low temperature solvent glass (77 K) and a weak solid-state

Název v anglickém jazyce

Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanolgues

Popis výsledku anglicky

Three N-analogues of Pechmann dye with identical aryl groups in the 5, 5'-positions (aryl=phenyl, 2-naphthyl, 2-thienyl) and carboxy ester groups in the 3,3'-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 confrmed as E isomers, i.e. holding an all-trans 1,6-diaryl-1,3,5-hexatriene backbone, with slight torsion of central C=C bond byX-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= phenyl)-643 nm (aryl = 2-thienyl) in accordance with time dependent DFTcalculations of excitation energies. No fluorescence was observed in solution, while all compounds fluoresce in low temperature solvent glass (77 K) and a weak solid-state

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/EE2.3.30.0021" target="_blank" >EE2.3.30.0021: Posílení excelentních týmů výzkumu a vývoje na Univerzitě Pardubice</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

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

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Svazek periodika

98

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

530-539

Kód UT WoS článku

000321169000029

EID výsledku v databázi Scopus

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