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Issue 16, 2013
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From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes

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Abstract

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 π system by an sp3 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, 1H 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.

Graphical abstract: From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes

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Publication details

The article was received on 21 Jan 2013, accepted on 25 Feb 2013 and first published on 25 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB40121A
Citation: Org. Biomol. Chem., 2013,11, 2685-2692
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    From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes

    Y. Ding, T. Li, X. Li, W. Zhu and Y. Xie, Org. Biomol. Chem., 2013, 11, 2685
    DOI: 10.1039/C3OB40121A

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