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Open AccessArticle

Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

Department of Chemistry, University of Connecticut, Unit 3060, Storrs, CT 06269–3060, USA
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Author to whom correspondence should be addressed.
Academic Editor: M. Graça P. M. S. Neves
Molecules 2020, 25(18), 4351; https://doi.org/10.3390/molecules25184351
Received: 14 August 2020 / Revised: 12 September 2020 / Accepted: 16 September 2020 / Published: 22 September 2020
meso-Phenyl- and meso-pentafluorophenyl-porpholactones, their metal complexes, as well as porphyrinoids directly derived from them are useful in a number of technical and biomedical applications, and more uses are expected to be discovered. About a dozen competing and complementary pathways toward their synthesis were reported. The suitability of the methods changes with the meso-aryl group and whether the free base or metal derivatives are sought. These circumstances make it hard for anyone outside of the field of synthetic porphyrin chemistry to ascertain which pathway is the best to produce which specific derivative. We report here on what we experimentally evaluated to be the most efficient pathways to generate the six key compounds from the commercially available porphyrins, meso-tetraphenylporphyrin (TPP) and meso-tetrakis(pentafluorophenyl)porphyrin (TFPP): free base meso-tetraphenylporpholactone (TPL) and meso-tetrakis(pentafluorophenyl)porpholactone (TFPL), and their platinum(II) and zinc(II) complexes TPLPt, TFPLPt, TPLZn, and TFPLZn, respectively. Detailed procedures are provided to make these intriguing molecules more readily available for their further study. View Full-Text
Keywords: porphyrin; porphyrinoids; porpholactone; oxidation porphyrin; porphyrinoids; porpholactone; oxidation
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Thuita, D.; Damunupola, D.; Brückner, C. Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes. Molecules 2020, 25, 4351.

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