Change search
ReferencesLink to record
Permanent link

Direct link
From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
Show others and affiliations
2013 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 11, no 16, 2685-2692 p.Article in journal (Refereed) Published
Abstract [en]

Most reported Zn2+ probes suffer from the interference of background fluorescence originated from the conjugated structures of commonly utilized fluorophores. In this work, three novel meso-hydroxyl group substituted dipyrromethanes DPMOH1-DPMOH3 were synthesized and found to be colourless and nonfluorescent due to the interruption of the conjugated p system by an sp(3) carbon between the two pyrrolic units. Interestingly, only the addition of Zn2+ to the solutions of DPMOH1-DPMOH3 promoted their oxidation to dipyrrin forms, and bright fluorescence "turn on" was observed due to the formation of corresponding dipyrrin complexes with the dipyrrin : zinc stoichiometry of 2 :1. Zn2+ detection mechanism was investigated by UV-Vis, fluorescence, H-1 NMR and HRMS analyses, which can be ascribed to the CHEF type fluorescence enhancement, resulting from good rigidity of the dipyrrin complexes. Hence, DPMOH1-DPMOH3 can be used as fluorescence turn-on Zn2+ probes with the advantage of no background fluorescence.

Place, publisher, year, edition, pages
2013. Vol. 11, no 16, 2685-2692 p.
Keyword [en]
Oxidative Cyclization, Aqueous-Solution, Energy-Transfer, Copper(Ii) Ion, Zinc Ions, Sensor, Chemosensors, Porphyrin, Emission, Design
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-122130DOI: 10.1039/c3ob40121aISI: 000316803900018ScopusID: 2-s2.0-84876972137OAI: diva2:621167

QC 20130514

Available from: 2013-05-14 Created: 2013-05-13 Last updated: 2013-05-14Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Search in DiVA

By author/editor
Li, Xin
By organisation
Theoretical Chemistry and Biology
In the same journal
Organic and biomolecular chemistry
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 25 hits
ReferencesLink to record
Permanent link

Direct link