Issue 47, 2016

A novel triphenylamine-BODIPY dendron: click synthesis, near-infrared emission and a multi-channel chemodosimeter for Hg2+ and Fe3+

Abstract

A novel triphenylamine-BODIPY based Schiff base fluorescent probe (TPA-BODIPY-OH) with an emission in the near-infrared (NIR) region was designed and prepared by click reaction. TPA-BODIPY-OH showed three emission bands at 510 nm, 598 nm and 670 nm, and can detect Fe3+ and Hg2+ ions with remarkable fluorescence enhancement in THF/H2O (v/v, 1 : 1, buffered with 10 mM HEPES pH = 7.4) based on the hydrolysis reaction of the –C[double bond, length as m-dash]N bond, and naked eye detection was realized with an obvious color change. The stoichiometry between the probe and ions was deduced from a Job's plot, which is 1 : 3 for TPA-BODIPY-OH/Fe3+ and 1 : 2 for TPA-BODIPY-OH/Hg2+, respectively. The dissociation constant value was found to be 1.35 × 10−16 M for TPA-BODIPY-OH/Fe3+ and 2.06 × 10−11 M for TPA-BODIPY-OH/Hg2+. The low detection limit was calculated from the titration results with the values of 5.15 × 10−7 M for TPA-BODIPY-OH/Fe3+ and 6.81 × 10−7 M for TPA-BODIPY-OH/Hg2+, respectively. In order to investigate the biological applications of TPA-BODIPY-OH, a living cell imaging experiment was carried out. The results demonstrate that TPA-BODIPY-OH can be successfully applied as a bioimaging agent in living cells. In addition, amino-group-functionalized silica fluorescent nanoparticles (FNPs) encapsulating the TPA-BODIPY-OH dyes were prepared and characterized by transmission electron microscopy. TPA-BODIPY-OH/SiO2 nanoparticles exhibit good dispersibility, and the quantum yield of FNPs at 657 nm was 42.3%.

Graphical abstract: A novel triphenylamine-BODIPY dendron: click synthesis, near-infrared emission and a multi-channel chemodosimeter for Hg2+ and Fe3+

Supplementary files

Article information

Article type
Paper
Submitted
21 Қыр. 2016
Accepted
21 Қаз. 2016
First published
21 Қаз. 2016

J. Mater. Chem. B, 2016,4, 7549-7559

A novel triphenylamine-BODIPY dendron: click synthesis, near-infrared emission and a multi-channel chemodosimeter for Hg2+ and Fe3+

B. Shen and Y. Qian, J. Mater. Chem. B, 2016, 4, 7549 DOI: 10.1039/C6TB02469F

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