Effect of rhenium(i) complexation on aza-Michael additions to 5-amino-1,10-phenanthroline with [18F]ethenesulfonyl fluoride towards PET optical tracer development

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dc.contributor.authorKlenner, MAen_AU
dc.contributor.authorPascali, Gen_AU
dc.contributor.authorZhang, Ben_AU
dc.contributor.authorCiancaleoni, Gen_AU
dc.contributor.authorMassi, Men_AU
dc.contributor.authorFraser, BHen_AU
dc.date.accessioned2021-08-10T01:40:16Zen_AU
dc.date.available2021-08-10T01:40:16Zen_AU
dc.date.issued2019-01-14en_AU
dc.date.statistics2021-08-10en_AU
dc.description.abstractConjugations with the recently developed [18F]ethenesulfonyl fluoride ([18F]ESF) were performed on 5-amino-1,10-phenanthroline, in its free form and coordinated to a rhenium(i) tricarbonyl complex, as a means of radiosynthesizing dual-modal optical and positron emission tomography (PET) tracers. The Michael-donating ability of the aromatic amine was noticeably perturbed on coordination with the rhenium(i) centre, resulting in decreased radiochemical yields from 34 %, in the case of the free ligand, to 1 %. We attribute the decreased nucleophilicity of the amine to metal deactivation from the electron-withdrawing feature of the rhenium(i) tricarbonyl centre, based on spectroscopic and computational evidence, thus highlighting this effect as a crucial parameter in designing late-stage metal coordination methods employing related aza-Michael additions. Photophysical analyses were also performed on the ESF-conjugated rhenium(i) complex, exhibiting a longer decay lifetime from the triplet metal-to-ligand charge transfer excited state when compared with the non-conjugated analogue. © CSIRO 1996-2021en_AU
dc.identifier.citationKlenner, M. A., Pascali, G., Zhang, B., Ciancaleoni, G., Massi, M., & Fraser, B. H. (2019). Effect of rhenium(i) complexation on aza-Michael additions to 5-amino-1,10-phenanthroline with [18F]ethenesulfonyl fluoride towards PET optical tracer development. Australian Journal of Chemistry, 72(4), 288-294. doi:10.1071/CH18512en_AU
dc.identifier.issn1445-0038en_AU
dc.identifier.issue4en_AU
dc.identifier.journaltitleAustralian Journal of Chemistryen_AU
dc.identifier.pagination288-294en_AU
dc.identifier.urihttps://doi.org/10.1071/CH18512en_AU
dc.identifier.urihttps://apo.ansto.gov.au/dspace/handle/10238/11292en_AU
dc.identifier.volume72en_AU
dc.language.isoenen_AU
dc.publisherCSIRO Publishingen_AU
dc.subjectFluorine 18en_AU
dc.subjectPhenanthrolinesen_AU
dc.subjectRheniumen_AU
dc.subjectPositron computed tomographyen_AU
dc.subjectEmission computed tomographyen_AU
dc.subjectTracer techniquesen_AU
dc.subjectRadiochemical analysisen_AU
dc.subjectLigandsen_AU
dc.subjectDecayen_AU
dc.titleEffect of rhenium(i) complexation on aza-Michael additions to 5-amino-1,10-phenanthroline with [18F]ethenesulfonyl fluoride towards PET optical tracer developmenten_AU
dc.typeJournal Articleen_AU
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