Phosphorus-centered (or P-centered)porphyrins are conjugated polycyclic ring systems consisting of either four pyrroles with inward-facing nitrogens and a phosphorus atom at their core or porphyrins with one of the four pyrroles substituted for a phosphole. Unmodified porphyrins are composed of pyrroles and linked by unsaturated hydrocarbon bridges often acting as multidentate ligands centered around a transition metal like Cu II, Zn II, Co II, Fe III.[1][2] Being highly conjugated molecules with many accessible energy levels, porphyrins are used in biological systems to perform light-energy conversion and modified synthetically to perform similar functions as a photoswitch or catalytic electron carriers.[1][3][4][5] Phosphorus III and V ions are much smaller than the typical metal centers and bestow distinct photochemical properties unto the porphyrin. Similar compounds with other pnictogen cores (As, Sb, Bi) or different polycyclic rings coordinated to phosphorus result in other changes to the porphyrin’s chemistry.[6][7]
Two varieties of P-centered porhpyrins: phosphorus core porphyrin (left) and phosphaporphyrin coordinated to a general metal, M (right).
^ abSchick, Alan; Schreiman, Irwin C.; Wagner, Richard W.; Lindsey, Jonathan S.; and Bocian, David F. (1989). “Spectroscopic characterization of porphyrin monolayer assemblies”. Journal of the American Chemical Society111 (4): 1344-1350. DOI: 10.1021/ja00186a030
^Gong, Xianchang; Milic, Tatjana; Xu, Chang; Batteas, James D.; and Drain, Charles Michael. (2002). “Preparation and Characterization of Porphyrin Nanoparticles”. Journal of the American Chemical Society124 (48): 14290-14291. DOI: 10.1021/ja027405z
^Reddya, D. Raghunath and Maiya, Bhaskar G. (2000). “A molecular photoswitch based on an ‘axial-bonding’ type phosphorus(v) porphyrin”. Chemical Communications 117-118 DOI: 10.1039/b007784o
^Poddutoori, Prashanth K.; Thomsen, Julianne M.; Milot, Rebecca L.; Sheehan, Stafford W.; et al. (2015). “Interfacial electron transfer in photoanodes based on phosphorus(v) porphyrin sensitizers co-deposited on SnO2 with the Ir(III)Cp* water oxidation precatalyst”. Journal of Material Chemistry3: 3868-3879. DOI: DOI: 10.1039/c4ta07018f
^Poddutoori, Prashanth K.; Lim, Gary N.; Pilkington, Melanie; D’Souza, Francis; and van der Est, Art. (2016). “Phosphorus(V) Porphyrin-Manganese(II) Terpyridine Conjugates: Synthesis, Spectroscopy, and Photo-Oxidation Studies on a SnO2 Surface”. Inorganic Chemistry55 (21): 11383-11395. DOI: 10.1021/acs.inorgchem.6b01924
^Barbour, Tanya; Belcher, Warwick J.; Brothers, Penelope J.; Rickard, Clifton E. F.; and Ware, David C. (1992). “Preparation of Group 15 (Phosphorus, Antimony, and Bismuth) Complexes of meso-Tetra-p-tolylporphyrin (TTP) and X-ray Crystal Structure of [Sb(TTP)(OCH(CH3)2)2]Cl”. Inorganic Chemistry31 (5): 746-754. DOI: 10.1021/ic00031a011
^Akiba, Kin-ya; Nadano, Ryo; Satoh, Wataru; Yamamoto, Yohsuke; Nagase, Shigeru; Ou, Zhongping; Tan, Xiaoyu; and Kadish, Karl M. (2001). “Synthesis, Structure, Electrochemistry, and Spectroelectrochemistry of Hypervalent Phosphorus(V) Octaethylporphyrins and Theoretical Analysis of the Nature of the PO Bond in P(OEP)(CH2CH3)(O)”. Inorganic Chemistry40 (22): 5553-5567. DOI: 10.1021/ic010595e
and 25 Related for: Phosphorus porphyrin information
Phosphorus-centered (or P-centered) porphyrins are conjugated polycyclic ring systems consisting of either four pyrroles with inward-facing nitrogens and...
porphyrin-like ligands), while organisms from an iron-depleted region preferred inorganic unbound iron or iron bound to chlorin e6 (another porphyrin-like...
state stabilization.: 2 An example of catalysts of this type is Sander's porphyrin trimer. A Diels Alder reaction between two pyridine functionalized substrates...
Aleshchenkov, S. E.; Cheprakov, A. V. (2012). "Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties" (PDF). J. Org. Chem. 77...
possible coordination sites; four are occupied by nitrogen atoms in a porphyrin ring, the fifth by an imidazole nitrogen in a histidine residue of one...
Magnesium in the center of the porphyrin ring in chlorophyll functions in a manner similar to the iron in the center of the porphyrin ring in heme. Magnesium...
ethylenediamine, which yields isomeric 14-membered tetraaza rings. Similarly, porphyrins, which feature 16-membered central rings, form in the absence of metal...
pigments or chromophores. In plants, these proteins are chlorophylls (a porphyrin derivative that absorbs the red and blue spectrums of light, thus reflecting...
kinase/AdoCbi-phosphate guanylyltransferase. This enzyme participates in porphyrin and chlorophyll metabolism. O'Toole GA, Escalante-Semerena JC (1995)....
The GOE is inferred to have been caused by cyanobacteria that evolved porphyrin-based photosynthesis, which produces dioxygen as a byproduct. The increasing...
A long-known example being ferrocenium [(C5H5)2Fe]+. Organoiron(III) porphyrin complexes, including alkyl and aryl derivatives, are also numerous. In...
appears to the eye. Chlorophyll is the primary pigment in plants; it is a porphyrin that absorbs red and blue wavelengths of light while reflecting green...
α‐diazocarbonyl compounds and a variety of N‐tosylhydrazones catalysed by Co(II)–porphyrin metalloradicals leading to the formation of ketenes, which subsequently...
core ligand called chlorin, and heme, which has a core ligand called porphyrin. They are responsible for the colour observed in plants and humans. Phthalocyanine...
Terzis, Aris; Strouse, Charles E. (1993). "Porphyrin sponges: conservative of host structure in over 200 porphyrin-based lattice clathrates". Journal of the...
surface science including surface modification, surface energy control, and porphyrin allayers. Feringa is a member of many chemical and scientific related...
corresponding aniline. Heating in acid with oxirane, followed by treatment with phosphorus oxychloride provided the bischloride, and removal of the protecting groups...
resistance to oxidation, arsenic trioxide differs from phosphorus trioxide, which readily combusts to phosphorus pentoxide. Reduction gives elemental arsenic or...
auxins, cytokinin, and indole acetic acid, as well as water-soluble porphyrins. These interactions may be physiologically relevant, since some of these...
of N,N′,N″-triethylenephosphoramide (TEPA), which contains tetrahedral phosphorus and is structurally akin to phosphate. It is manufactured by heating aziridine...
January 2007). "Framework coordination polymers of tetra(4-carboxyphenyl)porphyrin and lanthanide ions in crystalline solids". Dalton Transactions (30):...
Invertebrates such as insects or mollusks often display green colors because of porphyrin pigments, sometimes caused by diet. This can causes their feces to look...
possible coordination sites; four are occupied by nitrogen atoms in a porphyrin ring, the fifth by an imidazole nitrogen in a histidine residue of one...
Structure of a vanadium porphyrin compound (left) extracted from petroleum by Alfred E. Treibs, father of organic geochemistry. The close structural similarity...
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