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• W2894769665 endingPage "6166" @default.
• W2894769665 startingPage "6158" @default.
• W2894769665 abstract "The luminescence of oxazolones R 1 ‐C 6 H 4 CH=CC(O)O‐CN(R 2 ) ( 1a – 1j ) and imidazolones R 1 ‐C 6 H 4 CH=CC(O)NR 3 CN(R 2 ) ( 1k–1q ) has been examined. The new GFP‐like imidazolones (GFP = Green Fluorescent Protein) ( 1k – 1q ) have been prepared by reaction of the oxazolones with amines H 2 NR 3 and bis(trimethylsilyl)acetamide. The most intense fluorescence was found in push‐pull systems containing simultaneously strong electron‐donating and electron‐withdrawing substituents. The incorporation of the Pd atom into the molecular skeleton of oxazolones and imidazolones notably changes their luminescence. The reaction of oxazolones ( 1a–1j ) and imidazolones ( 1k–1q ) with Pd(OAc) 2 (1:1 molar ratio) in carboxylic acids gives the dinuclear [Pd{R 1 ‐C 6 H 3 CH=CC(O)OCN(R 2 )}(µ‐carboxylate)] 2 ( 2a–2j ) and [Pd{R 1 ‐C 6 H 3 CH=CC(O)NR 3 CN(R 2 )}(µ‐carboxylate)] 2 ( 2k–2q ) through regioselective C–H bond activation of the ortho position of the respective 4‐arylidene rings. Complexes 2a – 2q react with LiCl in MeOH to give the chloride‐bridge derivatives [Pd{R 1 ‐C 6 H 3 CH=CC(O)OCN(R 2 )}(µ‐Cl)] 2 ( 3a–3j ) and [Pd{R 1 ‐C 6 H 3 CH=CC(O)NR 3 CN(R 2 )}(µ‐Cl)] 2 ( 3k–3q ), which further react with Tl(acac) (acac = acetylacetonate) to give the mononuclear species [Pd(R 1 ‐C 6 H 3 CH=CC(O)OCN(R 2 )(acac)] ( 4a–4j ) and [Pd{R 1 ‐C 6 H 3 CH=CC(O)NR 3 CN(R 2 )(acac)}] ( 4k–4q ). Complexes 4o and 4q , having an orthopalladated push‐pull imidazolone, are strongly fluorescent, showing a notable increase of the quantum yield with respect to the free ligands 1o and 1q up of one order of magnitude." @default.
• W2894769665 created "2018-10-12" @default.
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• W2894769665 date "2018-11-13" @default.
• W2894769665 modified "2023-09-30" @default.
• W2894769665 title "Orthopalladation of GFP-Like Fluorophores Through C-H Bond Activation: Scope and Photophysical Properties" @default.
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• W2894769665 doi "https://doi.org/10.1002/ejoc.201800966" @default.
• W2894769665 hasPublicationYear "2018" @default.
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