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Fluorination of the tetraphenylethene core: synthesis, aggregation-induced emission, reversible mechanofluorochromism and thermofluorochromism of fluorinated tetraphenylethene derivatives

Abstract

The Suzuki-Miyaura cross-coupling reactions of bromoalkenes with fluorophenylboronic acids afforded 17 fluorinated tetraphenylethene (FTPE) compounds that have mere fluorine substituent(s) directly on the tetraphenylethene (TPE) core with different number and substitution position of the fluorine atom(s). The X-ray structures of four FTPEs show that these FTPE derivatives have C-H···F and C-H···π hydrogen bonds in the crystal packing. DFT calculations indicate that both the HOMO and LUMO orbitals of the FTPEs essentially have lower energy levels than those of the parent TPE, and the energy gaps are highly dependent on the substitution pattern. These FTPEs exhibit aggregation-induced emission characteristics as most TPE derivatives but the aggregation process was found to be gradual and time-dependent. The emission wavelengths of both aggregates from tetrahydrofuran/H2O and solids, and the corresponding emission quantum yields of the solid samples vary with different substitution pattern. In addition, two examples of these FTPEs show reversible mechanofluorochromic and thermofluorochromic property (the latter was only shown on silica gel), while the parent TPE does not exhibit mechanochromism under the same conditions.

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Publication details

The article was received on 27 Jan 2019, accepted on 12 Feb 2019 and first published on 13 Feb 2019


Article type: Paper
DOI: 10.1039/C9TC00511K
Citation: J. Mater. Chem. C, 2019, Accepted Manuscript

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    Fluorination of the tetraphenylethene core: synthesis, aggregation-induced emission, reversible mechanofluorochromism and thermofluorochromism of fluorinated tetraphenylethene derivatives

    H. Zhang, Y. Nie, J. Miao, D. Zhang, Y. Li, G. Liu, G. Sun and X. Jiang, J. Mater. Chem. C, 2019, Accepted Manuscript , DOI: 10.1039/C9TC00511K

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