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Issue 1, 2014
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Triaza-macrocyclic complexes of aluminium, gallium and indium halides: fast 18F and 19F incorporation via halide exchange under mild conditions in aqueous solution

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Abstract

Rapid and complete fluorination of the complexes [MCl3(L)] (L = Me3-tacn, BzMe2-tacn, M = Al, Ga, In) occurs at room temperature via reaction of a MeCN solution of the complex with 3 mol equiv. of KF in water. The Ga and In complexes are also readily fluorinated using R4NF (R = Me or nBu) in MeCN solution, whereas no reaction occurs with the Al species under these conditions. The distorted octahedral fac-trifluoride coordination at M is confirmed in solution by multinuclear (19F, 27Al, 71Ga and 115In) NMR spectroscopic studies, leading to sharp resonances with 19F–71Ga and 19F–115In couplings evident. The [MF3(L)] are extremely stable in aqueous solution and at low pH; they crystallise as tetrahydrates, [MF3(Me3-tacn)]·4H2O, with extended H-bonding networks formed through both F⋯H–O and O⋯H–O contacts. [InF3(BzMe2-tacn)]·1.2H2O also shows intermolecular F⋯H–O hydrogen bonding contacts. The prospects for developing this coordination chemistry further to take advantage of the high metal–fluoride bond energies to enable rapid, late-stage fluorination of large macromolecules under mild conditions for PET imaging applications in nuclear medicine are discussed. This work also demonstrates that F-18 radiolabelling to form [F-18] [GaF3(BzMe2-tacn)] is effected readily at room temperature in aqueous MeCN over 30–60 min on addition of 2.99 mol equiv. of [19F]–KFaq and 0.4 mL [18F]–KFaq (100–500 MBq) to [GaCl3(BzMe2-tacn)] with ca. 30% incorporation.

Graphical abstract: Triaza-macrocyclic complexes of aluminium, gallium and indium halides: fast 18F and 19F incorporation via halide exchange under mild conditions in aqueous solution

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Supplementary files

Article information


Submitted
26 Jul 2013
Accepted
24 Oct 2013
First published
25 Oct 2013

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2014,5, 381-391
Article type
Edge Article

Triaza-macrocyclic complexes of aluminium, gallium and indium halides: fast 18F and 19F incorporation via halide exchange under mild conditions in aqueous solution

R. Bhalla, C. Darby, W. Levason, S. K. Luthra, G. McRobbie, G. Reid, G. Sanderson and W. Zhang, Chem. Sci., 2014, 5, 381
DOI: 10.1039/C3SC52104D

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