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Issue 31, 2013
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A tetraphenylethene-substituted pyridinium salt with multiple functionalities: synthesis, stimuli-responsive emission, optical waveguide and specific mitochondrion imaging

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Abstract

In this work, a heteroatom-containing luminogen (TPE-Py) with multi-functionalities was synthesized in a reasonable yield by melding a pyridinium unit with tetraphenylethene through vinyl functionality. TPE-Py is weakly emissive in solution but becomes a strong emitter when aggregated as nanoparticle suspensions in poor solvents or in the solid state, displaying a phenomenon of aggregation-induced emission. Crystallization generally weakens and red-shifts the light emission. The crystalline aggregates of TPE-Py, however, emit stronger and bluer light than their amorphous counterparts. The solid-state emission of TPE-Py can be reversibly switched between green and yellow color by grinding–fuming and grinding–heating processes with a high contrast due to the transformation from the crystalline to the amorphous state and vice versa. The large Stokes shift and well-ordered molecular arrangement of the crystalline microrods of TPE-Py make it promising as an optical waveguide material with a low optical loss coefficient of ∼0.032 dB μm−1. TPE-Py works as a good fluorescent visualizer for specific staining of mitochondria in living cells with a high photostability, thanks to its hydrophobic and cationic features.

Graphical abstract: A tetraphenylethene-substituted pyridinium salt with multiple functionalities: synthesis, stimuli-responsive emission, optical waveguide and specific mitochondrion imaging

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Publication details

The article was received on 23 Apr 2013, accepted on 06 Jun 2013 and first published on 06 Jun 2013


Article type: Paper
DOI: 10.1039/C3TC30759J
Citation: J. Mater. Chem. C, 2013,1, 4640-4646
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    A tetraphenylethene-substituted pyridinium salt with multiple functionalities: synthesis, stimuli-responsive emission, optical waveguide and specific mitochondrion imaging

    N. Zhao, M. Li, Y. Yan, J. W. Y. Lam, Y. L. Zhang, Y. S. Zhao, K. S. Wong and B. Z. Tang, J. Mater. Chem. C, 2013, 1, 4640
    DOI: 10.1039/C3TC30759J

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