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Volume 196, 2017
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Bulky 4,6-disubstituted tetraphenylethene–naphthalimide dyad: synthesis, copolymerization, stimuli-responsive fluorescence and cellular imaging

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Abstract

We report the design and synthesis of a tetraphenylethene substituted with naphthalimide at the 4, 6 positions, named NI-2TPE. NI-2TPE exhibits strong solvent-dependent emission properties with combined ICT and AIE characteristics in THF–H2O systems. This probe was used directly on test papers to distinguish normal organic solvents using their emission colours under UV light based on its AIE and ICT nature. Thanks to the vinyl group in NI-2TPE, we synthesized a copolymer of NIPAM and NI-2TPE, termed P(NIPAM-co-NI-2TPE). The resulting polymer is highly soluble and fluorescent in water (ΦF = 15.4%). Due to the well-known thermo-responsive character of NIPAM, P(NIPAM-co-NI-2TPE) exhibits an interesting fluorescence change in response to various temperatures. Due to the thermo-induced shrinking of the PNIPAM chain, the fluorescence intensity gradually increased from 20 to 34 °C. As the temperature further increased from 34 to 90 °C, the fluorescence intensity decreased sharply, which was caused by the well-known thermal effects. Furthermore, we synthesized a P(HEA-co-NI-2TPE–TPP acrylate) copolymer, in which HEA is a hydrophilic unit, TPP is a mitochondria label and NI-2TPE a fluorescent probe. The corresponding polymer probe is highly soluble in water with FLQY = 7% and we have further applied this probe as a mitochondria targeted imaging tracker in HeLa cells successfully.

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Publication details

The article was received on 26 Jun 2016, accepted on 24 Aug 2016 and first published on 25 Aug 2016


Article type: Paper
DOI: 10.1039/C6FD00160B
Citation: Faraday Discuss., 2017,196, 439-454
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    Bulky 4,6-disubstituted tetraphenylethene–naphthalimide dyad: synthesis, copolymerization, stimuli-responsive fluorescence and cellular imaging

    Q. Hua, B. Xin, J. Liu, L. Zhao, Z. Xiong, T. Chen, Z. Chen, C. Li, W. Gong, Z. Huang and M. Zhu, Faraday Discuss., 2017, 196, 439
    DOI: 10.1039/C6FD00160B

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