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

   https://doi.org/10.3390/molecules25184351  

   Thuita, Damaris ; Damunupola, Dinusha ; Brückner, Christian ( September 2020 , Molecules)

   null (Ed.)

   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. 

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2. Bacterio- and Isobacteriodilactones by Stepwise or Direct Oxidations of meso -Tetrakis(pentafluorophenyl)porphyrin

   https://doi.org/10.1021/acs.joc.8b02628  

   Hewage, Nisansala ; Daddario, Pedro ; Lau, Kimberly S. ; Guberman-Pfeffer, Matthew J. ; Gascón, José A. ; Zeller, Matthias ; Lee, Christal O. ; Khalil, Gamal E. ; Gouterman, Martin ; Brückner, Christian ( December 2018 , The Journal of Organic Chemistry)
3. Studies on the mechanochemically induced chromene-annulation of meso -tetrakis(pentafluorophenyl)-2,3-dihydroxychlorin: Non-innocence of the grinding aids

   https://doi.org/10.1142/S1088424622500122  

   Mohan, Eric C. ; Atoyebi, Adewole O. ; Brückner, Christian ( April 2022 , Journal of Porphyrins and Phthalocyanines)

   The translation of the solution phase, base-induced formation of a chromene-annulated chlorin from the corresponding meso-tetrakis(pentafluorophenyl)-2,3-dihydroxychlorin using a mechanochemical approach (ball milling) is possible, but fraught with unexpectedly large difficulties associated with the grinding aids used. 

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4. Crystal structure of 2,3-dimethoxy- meso -tetrakis(pentafluorophenyl)morpholinochlorin methylene chloride 0.44-solvate

   https://doi.org/10.1107/S2056989020009093  

   Churchill, Serena B. ; Sharma, Meenakshi ; Brückner, Christian ; Zeller, Matthias ( August 2020 , Acta Crystallographica Section E Crystallographic Communications)

   null (Ed.)

   The title morpholinochlorin, C 46 H 16 F 20 N 4 O 3 , was crystallized from hexane/methylene chloride as its 0.44 methylene chloride solvate, C 46 H 16 F 20 N 4 O 3 ·0.44CH 2 Cl 2 . The morpholinochlorin was synthesized by stepwise oxygen insertion into a porphyrin using a `breaking and mending strategy': NaIO 4 -induced diol cleavage of the corresponding 2,3-dihydroxychlorin with in situ methanol-induced, acid-catalyzed intramolecular ring closure of the intermediate secochlorins bisaldehyde. Formally, one of the pyrrolic building blocks was thus replaced by a 2,3-dimethoxymorpholine moiety. Like other morpholinochlorins, the macrocycle of the title compound adopts a ruffled conformation, and the modulation of the porphyrinic π-system chromophore induces a red-shift of its optical spectrum compared to its corresponding chlorin analog. Packing in the crystal is governed by interactions involving the fluorine atoms of the pentafluorophenyl substituents, dominated by C—H...F interactions, and augmented by short fluorine...fluorine contacts, C—F...π interactions, and one severely slipped π-stacking interaction between two pentafluorophenyl rings. The solvate methylene chloride molecule is disordered over two independent positions around an inversion center with occupancies of two × 0.241 (5) and two × 0.199 (4), for a total site occupancy of 88%. 

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5. 1,8-Bis(borylamido)naphthalene Complexes of Lithium and Zinc(II) Including a Zinc(II) Isocyanide Adduct: 1,8-Bis(borylamido)naphthalene Complexes of Lithium and Zinc(II) Including a Zinc(II) Isocyanide Adduct

   https://doi.org/10.1002/ejic.201701099  

   Wang, Guocang ; Dias, H. V. ( December 2017 , European Journal of Inorganic Chemistry)