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Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes

Butler, Stephen J.; Delbianco, Martina; Evans, Nicholas H.; Frawley, Andrew T.; Pal, Robert; Parker, David; Puckrin, Robert S.; Yufit, Dmitry S.

Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes Thumbnail


Authors

Stephen J. Butler

Martina Delbianco

Nicholas H. Evans

Andrew T. Frawley

Robert S. Puckrin

Dmitry S. Yufit



Abstract

The 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.

Citation

Butler, S. J., Delbianco, M., Evans, N. H., Frawley, A. T., Pal, R., Parker, D., …Yufit, D. S. (2014). Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes. Dalton Transactions, 43(15), 5721-5730. https://doi.org/10.1039/c4dt00253a

Journal Article Type Article
Acceptance Date Feb 8, 2014
Online Publication Date Feb 21, 2014
Publication Date Apr 21, 2014
Deposit Date Jun 19, 2014
Publicly Available Date Jun 19, 2014
Journal Dalton Transactions
Print ISSN 1477-9226
Electronic ISSN 1477-9234
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 43
Issue 15
Pages 5721-5730
DOI https://doi.org/10.1039/c4dt00253a

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