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Photophysical Insights of Halogenated Dipyrrolonaphthyridine-Diones as Potential Photodynamic Therapy Agents. | LitMetric
We report the synthesis and photophysical characterization of novel halogenated dipyrrolonaphthyridine-diones (X -DPNDs, X = Cl, Br, and I), as candidates for photodynamic therapy (PDT) application. Apart from the heavy atom-induced spin-orbit coupling (SOC) dynamics in the investigated X -DPNDs, it was found that the position of the halogen atom (relative to the nitrogen of the pyrrole ring) also influenced the triplet excited state behavior. Interestingly, the faster/efficiency sensitization of O to O using X -DPND correlates with the rate of triplet population, k >1.6 × 10 s for I -DPND vs k >2.9 × 10 s for Cl -DPND and Br -DPND (where τ = 343 ± 3 ps for I -DPND and τ = 5-6 ns for Cl -DPND and Br -DPND are the lowest time constants/values for ISC). Furthermore, the heavy atom-induced SOC in Cl -DPND and Br -DPND did not lead to a reduction of the corresponding fluorescence (ca 75% vs 67% for the parent DPND). The attractive photophysical characteristics of Cl /Br -DPND put them on the landscape as not only promising PDT agents but also as fluorescence probes. The present study is a stepping stone in the development of novel organic photosystems for synergistic photomedicinal applications.
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