000084157 001__ 84157
000084157 005__ 20200117221615.0
000084157 0247_ $$2doi$$a10.1002/ejoc.201800966
000084157 0248_ $$2sideral$$a109415
000084157 037__ $$aART-2018-109415
000084157 041__ $$aeng
000084157 100__ $$aCollado, S.
000084157 245__ $$aOrthopalladation of GFP-Like Fluorophores Through C-H Bond Activation: Scope and Photophysical Properties
000084157 260__ $$c2018
000084157 5060_ $$aAccess copy available to the general public$$fUnrestricted
000084157 5203_ $$aThe luminescence of oxazolones R-1-C6H4CH=CC(O)O-CN(R-2) (1a-1j) and imidazolones R-1-C6H4CH=CC(O)NR3CN(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 H2NR3 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-C6H3CH=CC(O)OCN(R-2)}(mu-carboxylate)](2) (2a-2j) and [Pd{R-1-C6H3CH=CC(O)NR3CN(R-2)}(mu-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-C6H3CH=CC(O)OCN(R-2)}(mu-Cl)](2) (3a-3j) and [Pd{R-1-C6H3CH=CC(O)NR3CN(R-2)}(mu-Cl)](2) (3k-3q), which further react with Tl(acac) (acac = acetylacetonate) to give the mononuclear species [Pd(R-1-C6H3CH=CC(O)OCN(R-2)(acac)] (4a-4j) and [Pd{R-1-C6H3CH=CC(O)NR3CN(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.
000084157 536__ $$9info:eu-repo/grantAgreement/EUR/COST/CA15106-CHAOS$$9info:eu-repo/grantAgreement/ES/DGA-FEDER/E19-17R$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2013-40855-R
000084157 540__ $$9info:eu-repo/semantics/openAccess$$aAll rights reserved$$uhttp://www.europeana.eu/rights/rr-f/
000084157 590__ $$a3.029$$b2018
000084157 591__ $$aCHEMISTRY, ORGANIC$$b16 / 57 = 0.281$$c2018$$dQ2$$eT1
000084157 592__ $$a0.987$$b2018
000084157 593__ $$aPhysical and Theoretical Chemistry$$c2018$$dQ1
000084157 593__ $$aOrganic Chemistry$$c2018$$dQ1
000084157 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/acceptedVersion
000084157 700__ $$aPueyo, A.
000084157 700__ $$aBaudequin, C.
000084157 700__ $$aBischoff, L.
000084157 700__ $$0(orcid)0000-0001-8057-4861$$aJimenez, A.I.$$uUniversidad de Zaragoza
000084157 700__ $$0(orcid)0000-0003-3222-0828$$aCativiela, C.$$uUniversidad de Zaragoza
000084157 700__ $$aHoarau, C.
000084157 700__ $$0(orcid)0000-0001-9779-5820$$aUrriolabeitia, E.P.$$uUniversidad de Zaragoza
000084157 7102_ $$12010$$2760$$aUniversidad de Zaragoza$$bDpto. Química Inorgánica$$cÁrea Química Inorgánica
000084157 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000084157 773__ $$g44 (2018), 6158-6166$$pEUR J ORG CHEM$$tEuropean Journal of Organic Chemistry$$x1434-193X
000084157 8564_ $$s1398553$$uhttps://zaguan.unizar.es/record/84157/files/texto_completo.pdf$$yPostprint
000084157 8564_ $$s179962$$uhttps://zaguan.unizar.es/record/84157/files/texto_completo.jpg?subformat=icon$$xicon$$yPostprint
000084157 909CO $$ooai:zaguan.unizar.es:84157$$particulos$$pdriver
000084157 951__ $$a2020-01-17-21:50:49
000084157 980__ $$aARTICLE