《化学科学与工程前沿（英文）》
>> 2020年
第14卷
第1期
doi:
10.1007/s11705-019-1828-x
RESEARCH ARTICLE
Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF
Department of Chemistry, Royal College of Surgeons in Ireland (RCSI), Dublin 2, Ireland
录用日期：
2019-10-30
发布日期：
2019-10-30
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摘要
Bis-alkylsulfonic acid and polyethylene glycol (PEG)-substituted BF 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.
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