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 Jun 2016
Accepted
24 Aug 2016
First published
25 Aug 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements