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  • Butler Evans Parker Daltons 2014

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

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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. et al.
In: Dalton Transactions, Vol. 43, No. 15, 21.04.2014, p. 5721-5730.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Butler, SJ, Delbianco, M, Evans, NH, Fawley, AT, Pal, R, Parker, D, Puckrin, RS & Yufit, DS 2014, 'Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes', Dalton Transactions, vol. 43, no. 15, pp. 5721-5730. https://doi.org/10.1039/C4DT00253A

APA

Butler, S. J., Delbianco, M., Evans, N. H., Fawley, A. T., Pal, R., Parker, D., Puckrin, R. S., & 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

Vancouver

Butler SJ, Delbianco M, Evans NH, Fawley AT, Pal R, Parker D et al. Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes. Dalton Transactions. 2014 Apr 21;43(15):5721-5730. doi: 10.1039/C4DT00253A

Author

Butler, Stephen J. ; Delbianco, Martina ; Evans, Nicholas H. et al. / Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes. In: Dalton Transactions. 2014 ; Vol. 43, No. 15. pp. 5721-5730.

Bibtex

@article{9d2d3a0299374953aba61e2b28dbcdcc,
title = "Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes",
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.",
author = "Butler, {Stephen J.} and Martina Delbianco and Evans, {Nicholas H.} and Fawley, {Andrew T.} and Robert Pal and David Parker and Puckrin, {Robert S.} and Yufit, {Dmitry S.}",
year = "2014",
month = apr,
day = "21",
doi = "10.1039/C4DT00253A",
language = "English",
volume = "43",
pages = "5721--5730",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",
number = "15",

}

RIS

TY - JOUR

T1 - Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes

AU - Butler, Stephen J.

AU - Delbianco, Martina

AU - Evans, Nicholas H.

AU - Fawley, Andrew T.

AU - Pal, Robert

AU - Parker, David

AU - Puckrin, Robert S.

AU - Yufit, Dmitry S.

PY - 2014/4/21

Y1 - 2014/4/21

N2 - 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.

AB - 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.

U2 - 10.1039/C4DT00253A

DO - 10.1039/C4DT00253A

M3 - Journal article

VL - 43

SP - 5721

EP - 5730

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 15

ER -