Please use this identifier to cite or link to this item: https://apo.ansto.gov.au/dspace/handle/10238/11292
Title: Effect of rhenium(i) complexation on aza-Michael additions to 5-amino-1,10-phenanthroline with [18F]ethenesulfonyl fluoride towards PET optical tracer development
Authors: Klenner, MA
Pascali, G
Zhang, B
Ciancaleoni, G
Massi, M
Fraser, BH
Keywords: Fluorine 18
Phenanthrolines
Rhenium
Positron computed tomography
Emission computed tomography
Tracer techniques
Radiochemical analysis
Ligands
Decay
Issue Date: 14-Jan-2019
Publisher: CSIRO Publishing
Citation: Klenner, 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/CH18512
Abstract: Conjugations 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 1996-2021
URI: https://doi.org/10.1071/CH18512
https://apo.ansto.gov.au/dspace/handle/10238/11292
ISSN: 1445-0038
Appears in Collections:Journal Articles

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