About: Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues

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Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://www.sciencedirect.com/science/article/pii/S014372081300137X
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 bond by 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-state fluorescence of phenyl and 2-naphthyl derivatives in red/IR region was detected. 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 bond by 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-state fluorescence of phenyl and 2-naphthyl derivatives in red/IR region was detected. (en)
Title	Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues (en)
skos:prefLabel	Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues (en)
skos:notation	RIV/62690094:18470/13:50001296!RIV14-MSM-18470___
http://linked.open...avai/riv/aktivita	N
http://linked.open...avai/riv/aktivity	N
http://linked.open...iv/cisloPeriodika	3
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Lyčka, Antonín
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Hradec Králové / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	109568
http://linked.open...ai/riv/idVysledku	RIV/62690094:18470/13:50001296
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Density functional theory; Fluorescence; Absorption; NMR spectroscopy; X-ray diffraction techniques (en)
http://linked.open.../riv/klicoveSlovo	NMR spectroscopy Fluorescence Density functional theory X-ray diffraction techniques Absorption
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[7A1A92B31127]
http://linked.open...i/riv/nazevZdroje	Dyes and pigments
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	98
http://linked.open...iv/tvurceVysledku	Hrdina, Radim Luňák, Stanislav Padělková, Zdeňka Růžička, Aleš Vyňuchal, Jan Lyčka, Antonín Eliáš, Zdeněk Aysha, Tarek
http://linked.open...ain/vavai/riv/wos	000321169000029
issn	0143-7208
number of pages	10 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.dyepig.2013.04.010
http://localhost/t...ganizacniJednotka	18470

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