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Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(III) EuroTracker® dyes

Delbianco, M.; Lamarque, L.; Parker, D.

Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(III) EuroTracker® dyes Thumbnail


Authors

M. Delbianco

L. Lamarque



Abstract

The synthesis is described of a series of meta and para-substituted phenylsulfonate derivatives of very bright Eu(III) complexes with arylphosphinate groups and strongly absorbing arylalkynylpyridine moieties. The synthetic route involved the early introduction of trifluoroethyl esters to protect the sulfonic acid group, withstanding the use of reagents including acetyl bromide and mCPBA, and tolerating acid-catalysed esterification and Sonogashira reaction conditions. The Eu(III) complexes exhibit enhanced water solubility; their photophysical properties are not perturbed significantly by introduction of the anionic sulfonate groups.

Citation

Delbianco, M., Lamarque, L., & Parker, D. (2014). Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(III) EuroTracker® dyes. Organic and Biomolecular Chemistry, 12(40), 8061-8071. https://doi.org/10.1039/c4ob01143k

Journal Article Type Article
Publication Date Oct 28, 2014
Deposit Date Nov 14, 2014
Publicly Available Date Nov 20, 2014
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 12
Issue 40
Pages 8061-8071
DOI https://doi.org/10.1039/c4ob01143k

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