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Issue 18, 2017
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A novel (3,6-di-tert-butylcarbazol-9-yl) triphenylamine–BODIPY–tricyanofuran conjugated dye: synthesis and rapid naked-eye detection of hypochlorite

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Abstract

Herein, a colorimetric and ratiometric probe, BCPA–BODIPY–TCF, for hypochlorite (ClO) based on a D–π–A structure was synthesized through the Knoevenagel reaction, which consisted of donating groups (3,6-di-tert-butylcarbazol-9-yl)triphenylamine–BODIPY conjugated with a strong electronic acceptor group, 2-dicyanomethylene-4,5,5-trimethyl-3-cyano-2,5-dihydrofuran (tricyanofuran). Upon the addition of ClO, the probe displayed rapid identification, immediately accompanied with color change from purple to pink in one minute; this was attributed to the oxidative cleavage of an alkene linker between BODIPY and tricyanofuran. The introduction of tricyanofuran at the 2-position of BODIPY through a C[double bond, length as m-dash]C double bond made the absorption peak red-shift by 85 nm as compared to that of the precursor BCPA–BODIPY due to a strong intramolecular charge transfer (ICT) transition. Upon the addition of ClO, the absorption peak at 580 nm gradually decreased, and the absorption band centred at 500 nm concomitantly increased. The probe was highly selective for ClO detection without the interference of other anions and ROS. Additionally, a paper-based test strip was prepared and used as a naked-eye indicator for the presence of hypochlorite in practical tap water samples.

Graphical abstract: A novel (3,6-di-tert-butylcarbazol-9-yl) triphenylamine–BODIPY–tricyanofuran conjugated dye: synthesis and rapid naked-eye detection of hypochlorite

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Publication details

The article was received on 04 Jun 2017, accepted on 26 Jul 2017 and first published on 27 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01970J
Citation: New J. Chem., 2017,41, 9607-9612
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    A novel (3,6-di-tert-butylcarbazol-9-yl) triphenylamine–BODIPY–tricyanofuran conjugated dye: synthesis and rapid naked-eye detection of hypochlorite

    X. Xu and Y. Qian, New J. Chem., 2017, 41, 9607
    DOI: 10.1039/C7NJ01970J

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