Fig. 5: A general strategy for caging UV-to-NIR PS. | Nature Communications

Fig. 5: A general strategy for caging UV-to-NIR PS.

From: Tuning singlet oxygen generation with caged organic photosensitizers

Fig. 5

a Structures of chemically diverse organic PS (with their corresponding excitation maxima) and the synthesized caged analogs. 14: 2-thioxocoumarin, 15: thionaphthalimide, 16: benzophenoxazine, 17: phenothiazine. b Normalized absorbance spectra of caged compounds (gray lines) and their uncaged PS (from left to right, 14: blue, 15: orange, 16: red, 17: dark red; all at 100 μM in EtOH). c Singlet oxygen generation for compounds 15-17 and their caged analogs measured by monitoring the percentage of absorbance decrease of DPBF (300 µM in EtOH) before (gray bars) and after (colored bars) incubation with acid media (TFA:DCM, 1:1) or 1-10 mg mL−1 AuPd resins followed by illumination (15 (orange): 580 nm, 0.4 mW cm−2, 1 min; 16 (red): 640 nm, 1.5 mW cm−2, 40 min; 17 (dark red): 640 nm, 0.4 mW cm−2, 3 min). Values presented as means and error bars as SD (n = 3, independent experiments). d Singlet oxygen-mediated transformation of dihydroartemisinic acid into the antimalarial drug artemisinin. Conversion rates by HPLC-MS measurements under the same experimental conditions (640 nm illumination, all PS at 10% mol) using uncaged PS 17 (1 mM) or the caged PS 17b (1 mM) without or with AuPd resins (2 mg mL−1). Time-course analysis of the chemical transformation using caged PS 17b and AuPd resins is shown in Supplementary Fig. 31. Source data (c) are provided as a Source Data file.

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