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Lewis acid catalyzed condensation of pyrrole and 4-fluoro-2,6-dimethylbenzaldehyde followed by chemical oxidation afforded the corresponding chlorin along with the parent porphyrin. The subsequent metalation of the porphyrin-chlorin mixture in the presence of Zn(OAc)2•2H2O afforded Zn monoand di-hydroxychlorins in addition to the Zn porphyrin in a one-flask synthesis. This new direct hydroxylation reaction eliminates the need for highly toxic OsO4and H2S that are traditionally used for the generation of hydroxy chlorins. In addition to the full characterization of the zinc chlorins, we present cyclic voltammograms, steady-state absorption, and emission profiles of this rarely available class of compounds. Our findings show that Zn mono- and di-hydroxychlorins are stable compounds that possess exceptionally long triplet excited states in solution, making them promising candidates for photodynamic therapy.more » « lessFree, publicly-accessible full text available July 1, 2026
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Yee, Suwhan; Spitzack, Jason; Swanson, Jacob; Jung, Heejung; Rim, Donghyun (, Environmental Pollution)
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