From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes
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
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.
Oxidative Cyclization, Aqueous-Solution, Energy-Transfer, Copper(Ii) Ion, Zinc Ions, Sensor, Chemosensors, Porphyrin, Emission, Design
IdentifiersURN: urn:nbn:se:kth:diva-122130DOI: 10.1039/c3ob40121aISI: 000316803900018ScopusID: 2-s2.0-84876972137OAI: oai:DiVA.org:kth-122130DiVA: diva2:621167
QC 201305142013-05-142013-05-132013-05-14Bibliographically approved