000102111 001__ 102111
000102111 005__ 20230519145405.0
000102111 0247_ $$2doi$$a10.3390/molecules26051238
000102111 0248_ $$2sideral$$a124334
000102111 037__ $$aART-2021-124334
000102111 041__ $$aeng
000102111 100__ $$0(orcid)0000-0003-1882-2558$$aLaga, E.
000102111 245__ $$aFluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization
000102111 260__ $$c2021
000102111 5060_ $$aAccess copy available to the general public$$fUnrestricted
000102111 5203_ $$aThe goal of the work reported here was to amplify the fluorescent properties of 4-aryliden-5(4H)-oxazolones by suppression of the hula-twist non-radiative deactivation pathway. This aim was achieved by simultaneous bonding of a Pd center to the N atom of the heterocycle and the ortho carbon of the arylidene ring. Two different 4-((Z)-arylidene)-2-((E)-styryl)-5(4H)-oxazolones, the structures of which are closely related to the chromophore of the Kaede protein and substituted at the 2- and 4-positions of the arylidene ring (1a OMe; 1b F), were used as starting materials. Oxazolones 1a and 1b were reacted with Pd(OAc)2 to give the corresponding dinuclear orthometalated palladium derivates 2a and 2b by regioselective C-H activation of the ortho-position of the arylidene ring. Reaction of 2a (2b) with LiCl promoted the metathesis of the bridging carboxylate by chloride ligands to afford dinuclear 3a (3b). Mononuclear complexes containing the orthopalladated oxazolone and a variety of ancillary ligands (acetylacetonate (4a, 4b), hydroxyquinolinate (5a), aminoquinoline (6a), bipyridine (7a), phenanthroline (8a)) were prepared from 3a or 3b through metathesis of anionic ligands or substitution of neutral weakly bonded ligands. All species were fully characterized and the X-ray determination of the molecular structure of 7a was carried out. This structure has strongly distorted ligands due to intramolecular interactions. Fluorescence measurements showed an increase in the quantum yield (QY) by up to one order of magnitude on comparing the free oxazolone (QY < 1%) with the palladated oxazolone (QY = 12% for 6a). This fact shows that the coordination of the oxazolone to the palladium efficiently suppresses the hula-twist deactivation pathway.
000102111 536__ $$9info:eu-repo/grantAgreement/ES/MINECO/PID2019-104379RB-C21$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-106394GB-I00$$9info:eu-repo/grantAgreement/ES/DGA-FSE/E07-20R$$9info:eu-repo/grantAgreement/ES/DGA-FEDER/LMP144-18$$9info:eu-repo/grantAgreement/ES/DGA/E19-20R$$9info:eu-repo/grantAgreement/EUR/COST/CA15106-CHAOS
000102111 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000102111 590__ $$a4.927$$b2021
000102111 592__ $$a0.705$$b2021
000102111 594__ $$a5.9$$b2021
000102111 591__ $$aBIOCHEMISTRY & MOLECULAR BIOLOGY$$b114 / 297 = 0.384$$c2021$$dQ2$$eT2
000102111 593__ $$aAnalytical Chemistry$$c2021$$dQ1
000102111 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b65 / 180 = 0.361$$c2021$$dQ2$$eT2
000102111 593__ $$aDrug Discovery$$c2021$$dQ1
000102111 593__ $$aPharmaceutical Science$$c2021$$dQ1
000102111 593__ $$aMolecular Medicine$$c2021$$dQ1
000102111 593__ $$aOrganic Chemistry$$c2021$$dQ1
000102111 593__ $$aMedicine (miscellaneous)$$c2021$$dQ1
000102111 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000102111 700__ $$aDalmau, D.$$uUniversidad de Zaragoza
000102111 700__ $$0(orcid)0000-0003-3259-0933$$aArregui, S.
000102111 700__ $$0(orcid)0000-0001-9522-5840$$aCrespo, O.$$uUniversidad de Zaragoza
000102111 700__ $$0(orcid)0000-0001-8057-4861$$aJimenez, A.I.
000102111 700__ $$aPop, A.
000102111 700__ $$aSilvestru, C.
000102111 700__ $$0(orcid)0000-0001-9779-5820$$aUrriolabeitia, E.P.
000102111 7102_ $$12010$$2760$$aUniversidad de Zaragoza$$bDpto. Química Inorgánica$$cÁrea Química Inorgánica
000102111 773__ $$g26, 5 (2021), 1238 [19 pp]$$pMolecules (Basel, Online)$$tMolecules$$x1420-3049
000102111 8564_ $$s3849789$$uhttps://zaguan.unizar.es/record/102111/files/texto_completo.pdf$$yVersión publicada
000102111 8564_ $$s2874117$$uhttps://zaguan.unizar.es/record/102111/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000102111 909CO $$ooai:zaguan.unizar.es:102111$$particulos$$pdriver
000102111 951__ $$a2023-05-18-13:46:06
000102111 980__ $$aARTICLE