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Aggregation-responsive ON–OFF–ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

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Abstract

Fluorescence-switching dyes serve as important tools for bioimaging and environment sensing. Herein, we report a new type of molecule, tetrakis(benzo[b]furyl)ethene (TBFE), that undergoes two-wavelength ON–OFF–ON three-stage fluorescence switching triggered by aggregation. This compound features a sterically hindered tetrasubstituted ethene, made available by a hafnium-mediated McMurry coupling reaction. A fluorescent band of TBFE at 360 nm in THF disappears upon dilution with water towards 40% water in THF, giving way to a new peak at 510 nm. This switching behaviour is attributed to the combination of THF/H2O ratio-dependent aggregation-caused quenching and aggregation-induced emission, as supported by the change of size distribution measured by dynamic light scattering and scanning electron microscopy.

Graphical abstract: Aggregation-responsive ON–OFF–ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

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Publication details

The article was received on 03 Oct 2017, accepted on 17 Nov 2017 and first published on 27 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QM00453B
Citation: Mater. Chem. Front., 2018, Advance Article
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    Aggregation-responsive ON–OFF–ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

    H. Hamada, H. Tsuji and E. Nakamura, Mater. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QM00453B

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