NMR, Absorption and Fluorescence Parameters of Azlactones

İçli, Sıddık; Icil, Huriye; Alp, Serap; Koç, Halіl; McKillop, Alexander

doi:10.1080/00387019408006969

Cited by 37 publications

(14 citation statements)

References 11 publications

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“…4-Arylidene-5(4 H )-oxazolones are closely related to imidazolones, which are precursors of the former ( Figure 1 b). Unsaturated oxazolones are also luminescent and they have additional remarkable photophysical properties that include two-photon absorption (TPA), up-conversion, nonlinear optical properties and unique behavior as molecular switches [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization

et al. 2021

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The goal of the work reported here was to amplify the fluorescent properties of 4-aryliden-5(4H)-oxazolones by suppression of the hula-twist non-radiative deactivation pathway. This aim was achieved by simultaneous bonding of a Pd center to the N atom of the heterocycle and the ortho carbon of the arylidene ring. Two different 4-((Z)-arylidene)-2-((E)-styryl)-5(4H)-oxazolones, the structures of which are closely related to the chromophore of the Kaede protein and substituted at the 2- and 4-positions of the arylidene ring (1a OMe; 1b F), were used as starting materials. Oxazolones 1a and 1b were reacted with Pd(OAc)2 to give the corresponding dinuclear orthometalated palladium derivates 2a and 2b by regioselective C–H activation of the ortho-position of the arylidene ring. Reaction of 2a (2b) with LiCl promoted the metathesis of the bridging carboxylate by chloride ligands to afford dinuclear 3a (3b). Mononuclear complexes containing the orthopalladated oxazolone and a variety of ancillary ligands (acetylacetonate (4a, 4b), hydroxyquinolinate (5a), aminoquinoline (6a), bipyridine (7a), phenanthroline (8a)) were prepared from 3a or 3b through metathesis of anionic ligands or substitution of neutral weakly bonded ligands. All species were fully characterized and the X-ray determination of the molecular structure of 7a was carried out. This structure has strongly distorted ligands due to intramolecular interactions. Fluorescence measurements showed an increase in the quantum yield (QY) by up to one order of magnitude on comparing the free oxazolone (QY < 1%) with the palladated oxazolone (QY = 12% for 6a). This fact shows that the coordination of the oxazolone to the palladium efficiently suppresses the hula-twist deactivation pathway.

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Section: Introductionmentioning

confidence: 99%

Fluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization

et al. 2021

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“…The synthesis and purification of 2-phenyl-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-1), 2-(3,5-dinitrophenyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-2), 2-(4-nitrophenyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-3) and 2-(4-tolyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-4) were performed by using general preparation methods of azlactones as described in the literature (Icli 1994).…”

Section: Methodsmentioning

confidence: 99%

Optical Determination of Glucose with Glucose Oxidase Immobilized in PVC together with Fluorescent Oxazol‐5‐One Derivatives

Ozturk

Tımur²,

Alp

2008

Analytical Letters

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Fully reversible biosensors for glucose monitoring based on solid polyvinylchloride (PVC) films where the enzyme glucose oxidase (GOx) was incorporated together with 2-phenyl-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadec yl)benzylidene]-5-oxazolone (CPO-1), 2-(3,5-dinitrophenyl)-4-[4-(1,4,7,10-tetra oxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-2), 2-(4-nitrophenyl) -4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-3) and 2-(4-tolyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-4) derivatives have been developed. The limit of detection (LOD) values for glucose were found to be 1.47 Â 10 25 M, 2.01 Â 10 25 M, 0.89 Â 10 25 M, and 0.12 Â 10 25 M for CPO-1, CPO-2, CPO-3, and CPO-4, respectively (n ¼ 7). Sensor films were found to have excellent photostability.

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“…The synthesis and purification of 4-(2-furylmethylene)-2-phenyl-5-oxazolone (PFO) were performed by using general preparation methods of azlactones as described in the literature [21]. The membrane components, PVC (high molecular weight) and the plasticizer bis-(2-ethylhexyl)phthalate (DOP) were supplied by Fluka, lipophilic anionic additive reagent potassium tetrakis-(4-chlorophenyl)borate (PTCPB), tetrahydrofuran (THF), acetonitrile (ACN) and dichloromethane (DCM) were obtained from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Fluorescence emission studies of 4-(2-furylmethylene)-2-phenyl-5-oxazolone embedded in polymer thin film and detection of Fe3+ ion

2007

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NMR, Absorption and Fluorescence Parameters of Azlactones

Cited by 37 publications

References 11 publications

Fluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization

Fluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization

Optical Determination of Glucose with Glucose Oxidase Immobilized in PVC together with Fluorescent Oxazol‐5‐One Derivatives

Fluorescence emission studies of 4-(2-furylmethylene)-2-phenyl-5-oxazolone embedded in polymer thin film and detection of Fe3+ ion

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