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Download fileUtility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes
journal contribution
posted on 2015-09-15, 13:23 authored by Stephen ButlerStephen Butler, Martina Delbianco, Nicholas H. Evans, Andrew T. Frawley, Robert Pal, David Parker, Robert S. Puckrin, Dmitry S. YufitThe synthetic utility of europium complexes with three coordinated 4-bromopyridyl groups for chromophore elaboration has been assessed in palladium-catalysed Sonogashira coupling reactions, and in copper(I) mediated click reactions of the triazide derivative, generated in situ. The crystal structure of the Eu complex of a p-OMe-phenyl substituted triazole at 100 K is reported in which the pendant triazole sensitising moieties interdigitate in the solid-state lattice. The triazole complex can be separated into Δ and Λ enantiomers by chiral HPLC but is weakly emissive in methanol (ε 5.5 mM−1 cm−1; λexc 320 nm; ϕ 0.2%), contrasting with a set of four alkynyl–aryl derivatives which are one thousand times brighter and absorb strongly with broad absorption maxima in the range 332 to 360 nm. An enantiopure europium complex gives an intense CPL signal in solution that is the strongest yet reported.
Funding
We thank the ERC (FCC 266804), CISbio Bioassays, the Royal Society and EPSRC for support.
History
School
- Science
Department
- Chemistry
Published in
DALTON TRANSACTIONSVolume
43Issue
15Pages
5721 - 5730 (10)Citation
BUTLER, S.J. ... et al, 2014. Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes. Dalton Transactions, 43 (15), pp. 5721 - 5730.Publisher
© The Royal Society of ChemistryVersion
- AM (Accepted Manuscript)
Publisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Publication date
2014Notes
This is the accepted version of an article subsequently published in the journal, Dalton Transactions [© The Royal Society of Chemistry]. The definitive version is available at: http://dx.doi.org/10.1039/c4dt00253a.ISSN
1477-9226Publisher version
Language
- en