Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
A Versatile Long-Wavelength-Absorbing Scaffold for Eu-Based Responsive Probes
Stockholm University, Faculty of Science, Department of Organic Chemistry. Uppsala University, Sweden.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. Uppsala University, Sweden.
2013 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 9, 3099-3109 p.Article, review/survey (Refereed) Published
Abstract [en]

Coumarin-sensitized, long-wavelength-absorbing luminescent EuIII-complexes have been synthesized and characterized. The lanthanide binding site consists of a cyclen-based chelating framework that is attached through a short linker to a 7-hydroxycoumarin, a 7-B(OH)2-coumarin, a 7-O-(4-pinacolatoboronbenzyl)-coumarin or a 7-O-(4-methoxybenzyl)-coumarin. The syntheses are straightforward, use readily available building blocks, and proceed through a small number of high-yielding steps. The sensitivity of coumarin photophysics to the 7-substituent enables modulation of the antenna-absorption properties, and thus the lanthanide excitation spectrum. Reactions of the boronate-based functionalities (cages) with H2O2 yielded the corresponding 7-hydroxycoumarin species. The same species was produced with peroxynitrite in a x106107-fold faster reaction. Both reactions resulted in the emergence of a strong approximate to 407nm excitation band, with concomitant decrease of the 366nm band of the caged probe. In aqueous solution the methoxybenzyl caged Eu-complex was quenched by ONOO. We have shown that preliminary screening of simple coumarin-based antennae through UV/Vis absorption spectroscopy is possible as the changes in absorption profile translate with good fidelity to changes in EuIII-excitation profile in the fully elaborated complex. Taken together, our results show that the 7-hydroxycoumarin antenna is a viable scaffold for the construction of turn-on and ratiometric luminescent probes.

Place, publisher, year, edition, pages
2013. Vol. 19, no 9, 3099-3109 p.
Keyword [en]
coumarins, cyclen, europium, fluorescent probes, lanthanides, reactive oxygen species
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-88682DOI: 10.1002/chem.201203957ISI: 000315142300022OAI: oai:DiVA.org:su-88682DiVA: diva2:613008
Funder
Swedish Research Council
Note

AuthorCount:4;

Available from: 2013-03-26 Created: 2013-03-25 Last updated: 2017-12-06Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Pershagen, EliasIlchenko, Nadia O.
By organisation
Department of Organic Chemistry
In the same journal
Chemistry - A European Journal
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 40 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf