Journal of Inclusion Phenomena and Macrocyclic Chemistry p. 567 - 575 (2011)
Update date:2022-08-04
Topics:
Bradbury, Adam J.
Lincoln, Stephen F.
Wainwright, Kevin P.
Our observations that 1-[2-[(9-anthracenylmethylamino)ethyl)-4,7,10- tris[(2S)-2-hydroxy-3-phenoxypropyl]-1,4,7,10-tetraazacyclododecane, L 1, complexes Cd(II) to form fluorescent [CdL1] 2+ which undergoes a fluorescence change when it acts as an aromatic anion receptor complex has caused us to explore further the potential development of an interesting sequestration/sensor system. Accordingly, three new, octadentate, fluorescent, macrocyclic ligands, 1-[2-[(9-anthracenylmethyl) ((2S)-2-hydroxy-3-phenoxypropyl)amino]ethyl]-4,7,10-tris[(2S) -2-hydroxy-3-phenoxypropyl]-1,4,7,10-tetraazacyclododecane, (L2), 1-[2-[(9-anthracenyl-methyl)((2S)-2-hydroxy-3-(4′-methyl)phenoxypropyl) amino]ethyl]-4,7,10-tris[(2S)-2-hydroxy-3-(4′-methyl)phenoxypropyl]-1,4,7, 10-tetraazacyclododecane, (L3), and 1-[2-[(9-anthracenylmethyl)((2S)- 2-hydroxy-3-(4′-t-butyl)phenoxypropyl)amino]ethyl]-4,7,10-tris[(2S) -2-hydroxy-3-(4′-t-butyl)phenoxypropyl]-1,4,7,10-tetraazacyclododecane, (L4), have been prepared with a view to using their metal complexes to study aromatic anion sequestration. The eight-coordinate Cd(II) complexes of L2 and L3, [CdL2](ClO4) 2?5H2O and [CdL3](ClO4) 2?2H2O?2Et2O are both capable of acting as receptors for a range of aromatic oxoanions. This is demonstrated by perturbation of the anthracene derived fluorescence emission intensity as the guest aromatic oxoanion and the receptor complex combine. In 20% aqueous 1,4-dioxane the receptor complex/aromatic oxoanion association constants are in the range of 103.2 M-1 (guest = p-hydroxybenzoate) to 107.3 M-1 (guest = 3,4,5-trihydroxybenzoate).
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