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Issue 9, 2016
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A colour-tunable chiral AIEgen: reversible coordination, enantiomer discrimination and morphology visualization

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Abstract

We present a conceptually new approach to synthesise a boron-containing Aggregation-Induced Emissive Luminogen (AIEgen) with a chiral chromophore. An intramolecular N–B coordinating bond results in a low-energy transition that renders the material red-emissive in a solid state. By competitive binding of nucleophiles to the boron atom, this bond is replaced in favour of an intermolecular coordinating bond, which results in a tremendous blue-shift in both the absorption and emission. A supportive DFT computation elucidates that a breakage of the intramolecular N–B coordinating bond causes a tremendous loss of conjugation in the LUMO, resulting in a larger energy gap. Owing to the fact that our scaffold is intrinsically chiral and Lewis-acidic, we demonstrate how our AIEgen discriminates between two pairs of enantiomers in a simple UV-vis measurement. Furthermore, the binding capabilities are exploited to stain polymer blends that comprised a non-coordinating and a Lewis-basic polymer. The red fluorescence that originates only from domains of the non-coordinating polymer is conveniently detected by a fluorescence microscope. Thus, compared to current analytical methods, we present a cheaper and faster methodology to study the micro-morphologies of certain polymer blends.

Graphical abstract: A colour-tunable chiral AIEgen: reversible coordination, enantiomer discrimination and morphology visualization

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Publication details

The article was received on 12 Apr 2016, accepted on 31 May 2016 and first published on 02 Jun 2016


Article type: Edge Article
DOI: 10.1039/C6SC01614F
Citation: Chem. Sci., 2016,7, 6106-6114
  • Open access: Creative Commons BY license
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    A colour-tunable chiral AIEgen: reversible coordination, enantiomer discrimination and morphology visualization

    J. Roose, A. C. S. Leung, J. Wang, Q. Peng, H. H.-Y. Sung, I. D. Williams and B. Z. Tang, Chem. Sci., 2016, 7, 6106
    DOI: 10.1039/C6SC01614F

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