Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 2, 2017

Copper-assisted azide–alkyne cycloaddition chemistry as a tool for the production of emissive boron difluoride 3-cyanoformazanates

Author affiliations

Abstract

The synthesis and characterization of emissive boron difluoride (BF2) complexes of 3-cyanoformazanate ligands produced using copper-assisted azide–alkyne cycloaddition (CuAAC) chemistry is described. Detailed spectroscopic and electrochemical characterization of benzyl-functionalized complexes served as models and demonstrated that triazole formation at the N-aryl substituents of the formazanate ligand scaffold led to red-shifted absorption and emission maxima and more difficult electrochemical reduction compared to alkyne-substituted precursors. CuAAC chemistry was also used to append ferrocene and tetraethylene glycol substituents to the formazanate backbone. In the case of the ferrocene-substituted complexes, fluorescence was quenched and a reversible oxidation feature (in addition to the reduction features associated with formazanate complexes) was observed using cyclic voltammetry. Treatment with NOBF4 oxidized ferrocene to ferrocenium and resulted in the reestablishment of fluorescence. Tetraethylene glycol substitution produced the first water soluble BF2 formazanate, which was shown to distribute throughout the cytoplasm and nucleus of mouse fibroblast cells when studied as a fluorescence imaging agent.

Graphical abstract: Copper-assisted azide–alkyne cycloaddition chemistry as a tool for the production of emissive boron difluoride 3-cyanoformazanates

Supplementary files

Article information


Submitted
18 Oct 2016
Accepted
02 Nov 2016
First published
08 Nov 2016

This article is Open Access

Org. Chem. Front., 2017,4, 178-190
Article type
Research Article

Copper-assisted azide–alkyne cycloaddition chemistry as a tool for the production of emissive boron difluoride 3-cyanoformazanates

S. M. Barbon, S. Novoa, D. Bender, H. Groom, L. G. Luyt and J. B. Gilroy, Org. Chem. Front., 2017, 4, 178 DOI: 10.1039/C6QO00640J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements