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Guided by demands for functional porphyrins with tunable electronic properties, high photostability, and controlled supramolecular organization, we report a synthetic approach to\n                    <jats:italic>meso<\/jats:italic>\n                    \u2010tetrakis[4\u2010(diethoxyphosphoryl)\u20102,3,5,6\u2010tetrafluorophenyl]porphyrin (H\n                    <jats:sub>2<\/jats:sub>\n                    TF\n                    <jats:sub>4<\/jats:sub>\n                    PPP), which combines the advantages of diethyl phosphonate and fluorine substituents within a highly symmetrical porphyrin molecule. X\u2010ray diffraction analysis of H\n                    <jats:sub>2<\/jats:sub>\n                    TF\n                    <jats:sub>4<\/jats:sub>\n                    PPP reveals that diethyl phosphonates govern the crystal packing, while the macrocycles avoid\n                    <jats:italic>\u03c0\u2013\u03c0<\/jats:italic>\n                    stacking. Zn(II) and Pd(II) complexes with H\n                    <jats:sub>2<\/jats:sub>\n                    TF\n                    <jats:sub>4<\/jats:sub>\n                    PPP were prepared in high yields. In contrast, insertion of In(III) ions exhibiting strong Lewis acidity was accompanied by partial hydrolysis of phosphonate groups. H\n                    <jats:sub>2<\/jats:sub>\n                    TF\n                    <jats:sub>4<\/jats:sub>\n                    PPP and its Zn(II) and Pd(II) complexes efficiently generate singlet oxygen displaying a good solubility in various organic solvents. The noble\u2010metal\u2010free porphyrin H\n                    <jats:sub>2<\/jats:sub>\n                    TF\n                    <jats:sub>4<\/jats:sub>\n                    PPP surpasses Pd(II) complex of non\u2010fluorinated analogue (PdTPPP) in photocatalytic performance, enabling sustainable oxidation of sulfides to sulfoxides with oxygen. H\n                    <jats:sub>2<\/jats:sub>\n                    TF\n                    <jats:sub>4<\/jats:sub>\n                    PPP forms a stable Langmuir monolayer which can be transferred onto solid substrates, yielding dense single\u2010layer films containing fiber\u2010shaped nanoparticles. The films thus obtained are emissive and their photostability surpasses that of H\n                    <jats:sub>2<\/jats:sub>\n                    TPPP films. Water\u2010soluble porphyrins H\n                    <jats:sub>2<\/jats:sub>\n                    TF\n                    <jats:sub>4<\/jats:sub>\n                    PPP\u2010A and PdTF\n                    <jats:sub>4<\/jats:sub>\n                    PPP\u2010A with phosphonic acid groups were also prepared and briefly investigated.\n                  <\/jats:p>","DOI":"10.1002\/chem.71118","type":"journal-article","created":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T21:30:02Z","timestamp":1778880602000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and Functional Properties of Fluorinated Phosphonate\u2010Substituted Porphyrins: Excellent Photosensitizers and Robust Precursors for Photoactive Langmuir\u2013Schaefer 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