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Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores

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journal contribution
posted on 15.11.2021, 17:06 by Dan WuDan Wu, Gonzalo Durán-Sampedro, Donal O'SheaDonal O'Shea
Bis-alkylsulfonic acid and polyethylene glycol (PEG)-substituted BF2 azadipyrromethenes have been synthesized by an adaptable and versatile route. Only four synthetic stages were required to produce the penultimate fluorophore compounds, containing either two alcohol or two terminal alkyne substituents. The final synthetic step introduced either sulfonic acid or polyethylene glycol groups to impart aqueous solubility. Sulfonic acid groups were introduced by reaction of the bis-alcohol-substituted fluorophore with sulfur trioxide, and a double Cu(I)-catalyzed cycloaddition reaction between the bis-alkyne fluorophore and methoxypolyethylene glycol azide yielded a neutral bis-pegylated derivative. Both fluorophores exhibited excellent near-infrared (NIR) photophysical properties in methanol and aqueous solutions. Live cell microscopy imaging revealed efficient uptake and intracellular labelling of cells for both fluorophores. Their simple synthesis, with potential for last-step structural modifications, makes the present NIR-active azadipyrromethene derivatives potentially useful as NIR fluorescence imaging probes for live cells.

Funding

European Union’s Horizon 2020 research and innovation program, under the Marie Sklodowska-Curie grant agreement No. 707618

History

Comments

This is a post-peer-review, pre-copyedit version of an article published in Frontiers of Chemical Science and Engineering. The final authenticated version is available online at: https://doi.org/10.1007/s11705-019-1828-x

Published Citation

Wu D, Durán-Sampedro G, O’Shea DF. Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores. Front. Chem. Sci. Eng. 2020;14:97–104

Publication Date

26 October 2019

Department/Unit

  • Chemistry

Research Area

  • Cancer
  • Surgical Science and Practice
  • Chemistry and Pharmaceutical Sciences

Publisher

Springer Nature Switzerland AG

Version

  • Accepted Version (Postprint)