Volume 196, 2017

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

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.

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
26 6 2016
Accepted
24 8 2016
First published
25 8 2016

Faraday Discuss., 2017,196, 439-454

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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