Boron dipyrromethene (BODIPY)-derived dyes are generally
superior
emitters, but their absorption and emission fail to match the bio-active
optical window (650–900 nm). In this work, we explored four
bisBODIPY dyes (PB1–PB4) with easy-to-go synthesis, good solubility,
high photostability, and high emission quantum yield in the deep-red
region. Methyl and ethyl groups were introduced in these BODIPY dyes
to improve their solubility. PB4 having a fused coplanar plane was
synthesized and compared to PB1–PB3 having a non-fused structure.
Their geometric structure was confirmed by single-crystal analysis,
and their electronic structure, along with one-photon and two-photon
absorptions, was analyzed by time-dependent functional theory calculation.
Their absorption/emission spectra, emission quantum yields, and lifetimes
were compared. It was found that the fused coplanar structure successfully
red shifted PB4 absorption/emission to the deep-red region (698/720
nm), with a quantum yield of 0.58. PB4 showed an amplified spontaneous
emission effect with an output efficiency of 6.0% at a pumping power
of 3000 μJ. An improved photodynamic therapy (PDT) performance
was observed from PB4 via in vitro and in vivo experiments. The practical
PDT performance was evaluated by cell availability. Upon a 980 nm
laser radiation of 5 min, the cell viability was decreased to ∼15%.