RT Journal Article
T1 Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores
A1 Wu, Dan
A1 Durán Sampedro, Gonzalo
A1 O’Shea, Donal
AB 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.
PB Springer
SN 2095-0179
YR 2019
FD 2019
LK https://hdl.handle.net/20.500.14352/95500
UL https://hdl.handle.net/20.500.14352/95500
LA eng
NO Wu, D., Durán-Sampedro, G. & O’Shea, D.F. Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores. Front. Chem. Sci. Eng. 14, 97–104 (2020). https://doi.org/10.1007/s11705-019-1828-x
NO European Commission
DS Docta Complutense
RD 13 abr 2025