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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
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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
Identifiers
URN: urn:nbn:se:kth:diva-122130DOI: 10.1039/c3ob40121aISI: 000316803900018Scopus ID: 2-s2.0-84876972137OAI: oai:DiVA.org:kth-122130DiVA: diva2:621167
Note

QC 20130514

Available from: 2013-05-14 Created: 2013-05-13 Last updated: 2017-12-06Bibliographically approved

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Li, Xin

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