- Development of antimicrobial laser-induced photodynamic therapy based on ethylcellulose/chitosan nanocomposite with 5,10,15,20-tetrakis(M-hydroxyphenyl)porphyrin
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The development of new antimicrobial strategies that act more efficiently than traditional antibiotics is becoming a necessity to combat multidrug-resistant pathogens. Here we report the effi-cacy of laser-light-irradiated 5,10,15,20-tetrakis(m-hydroxyphenyl)porphyrin (mTHPP) loaded onto an ethylcellulose (EC)/chitosan (Chs) nanocomposite in eradicating multi-drug resistant Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans. Surface loading of the ethylcelllose/chitosan composite with mTHPP was carried out and the resulting nanocomposite was fully characterized. The results indicate that the prepared nanocomposite incorporates mTHPP inside, and that the composite acquired an overall positive charge. The incorporation of mTHPP into the nanocomposite enhanced the photo-and thermal stability. Different laser wavelengths (458; 476; 488; 515; 635 nm), powers (5–70 mW), and exposure times (15–45 min) were investigated in the antimicrobial pho-todynamic therapy (aPDT) experiments, with the best inhibition observed using 635 nm with the mTHPP EC/Chs nanocomposite for C. albicans (59 ± 0.21%), P. aeruginosa (71.7 ± 1.72%), and S. aureus (74.2 ± 1.26%) with illumination of only 15 min. Utilization of higher doses (70 mW) for longer periods achieved more eradication of microbial growth.
- Hasanin, Mohamed S.,Abdelraof, Mohamed,Fikry, Mohamed,Shaker, Yasser M.,Sweed, Ayman M. K.,Senge, Mathias O.
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- The synthesis of new potential photosensitizers
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Abstract Several new derivatives of tetrakis(hydroxyphenyl)porphyrin were synthesized and their physicochemical data were established. These data were further assessed in terms of the synthesized compounds' usefulness as potential photosensitizers in anticancer photodynamic therapy. Absorption and fluorescence spectra, as well as triplet state lifetime were determined along with the compounds' stability and capacity to generate singlet oxygen. They obtained were compared to the corresponding data pertaining to a well-known and clinically admitted photosensitizing drug (Foscan).
- Rojkiewicz, Marcin,Ku?, Piotr,Kozub, Patrycja,Kempa, Marta
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- Effects of substituents on the photophysical properties of symmetrical porphyrins
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Porphyrin compounds having groups that mimic the phenolic moiety of m- and p-isomers of 5,10,15,20-tetrakis(hydroxyphenyl) porphyrin (THPP) have been synthesized along with 5,10,15,20-tetrakis(heteroaryl) porphyrins bearing 2-thienyl and 5-thiazolyl groups. Absorption and fluorescence spectroscopy, including fluorescence lifetime (τf) and quantum yield (Φf) measurements, were employed to characterize the singlet excited state of all compounds, using 5,10,15,20-tetraphenylporphyrin (H 2TPP) as a standard (Φf = 0.12 in DMF). The generation of singlet oxygen by each porphyrin photosensitizer was measured as the singlet oxygen quantum yield (ΦΔ), using H2TPP as a standard (ΦΔ = 0.64 in DMF). Partition coefficients were determined using 2-octanol as the organic phase and PBS solution as the aqueous phase. Fluorescence quantum yields ranged from 0.01 to 0.18 for all compounds, with heteroaryl porphyrins having the lowest values. Singlet oxygen quantum yields ranged from 0.40 to 0.65, with heteroaryl porphyrins having the highest values, showing them to be better sensitizers than m- and p-THPP. Log P values were all >1 showing higher solubility in the 2-octanol layer.
- Ormond, Alexandra B.,Freeman, Harold S.
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- Synthesis, photophysical properties and DNA-Binding Studies of p-Hydroxy and m-Hydroxy Amphiphilic Porphyrins
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Three p-hydroxy and m-hydroxy amphiphilic porphyrins had been synthesized and fully characterized by 1H NMR, IR and FAB-MS. Their photophysical properties were also determined. Furthermore, the UV-visible absorption and fluorescence emission titration exp
- Zhang, Jie,Jin, Haiwei,Gao, Dongchun,Jia, Wenping,Li, Fang,Zhang, Ping,Song, Tongtong,Wang, Jiali
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- Synthesis and biological distribution study of a new carbon-11 labeled porphyrin for PET imaging. Photochemical and biological characterization of the non-labeled porphyrin
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Ideal reaction conditions were found to promote the "cold" monomethylation of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin with CH3I, at minute time scale, in the presence of base. The photophysical characterization, cellular uptake and dark cytotoxicity of the resulting monomethylated porphyrin were appraised. Moreover, the syntheses of the corresponding labeled porphyrin, using short-lived carbon-11, prepared in the automated radiolabeling system were efficiently performed. The purification of the labeled product was achieved via preparative HPLC with high radiochemical purity and specific radioactivity. Preliminary studies on the biodistribution of 5,10,15-tris(3-hydroxyphenyl)-20-(3-[11C]methoxyphenyl)porphyrin carried out in a BALB/C normal mouse, using PET imaging, showed that the liver is the main pathway for excretion.
- Gonc?lves, Nuno P. F.,Sim?es, Ana V. C.,Abreu, Artur R.,Abrunhosa, Antero J.,D?browski, Janusz M.,Pereira, Mariette M.
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- Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air
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Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.
- Hanafiah, Marlia M.,Lakkaboyana, Sivarama Krishna,Lakshmidevi, Jangam,Marella, Ravi Kumar,Naidu, Bandameeda Ramesh,Prasad, Sana Siva,Venkateswarlu, Katta
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- New approach for the synthesis, docking of new porphyrins and their antitumor activity
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A new methodology for the synthesis of a new series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 5a-5d, 6a-6c, 7 and 8 is presented. Structures of new compounds were established based on both elemental and spectral data. Cytotoxicity activity of the newly synthesized compounds was investigated against two human cell lines MCF-7 and HepG2. Molecular docking was performed to investigate the binding between the most active porphyrin derivatives and Bcl-2 molecular biomarkers in HepG2 cells.
- Tawfik, Eman H.,Fadda, Ahmed A.,Soliman, Nanees N.,Abou-Zeid, Laila,Negm, Amr
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p. 251 - 259
(2019/02/24)
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- A four-phenyl porphine production method (by machine translation)
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The invention discloses a production method for tetraphenyl porphin. The production method includes the steps that 1, pyrrole and aromatic aldehyde are prepared into a mixed solution for standby application; 2, solvent is added into a polymerization reactor, the pressure of the polymerization reactor is maintained at 1-5 atm, the mixed solution obtained in the step 1 starts to be dripped to start a polymerization reaction, after the reaction is finished, reaction products are cooled to normal temperature, and filter liquor and a filter cake are obtained through filtration; 3, the filter cake obtained in the step 2 and propionic acid are added into an oxidation reactor, oxygen-containing gas is introduced to carry out an oxidation reaction, cooling is carried out after oxidation is finished, a solid and filter liquor are obtained through filtration, and the solid is washed and dried to obtain the tetraphenyl porphin. The production method has the advantages of being high in yield, safe and environmentally friendly, separation and purification are easy, and the production quality is stable.
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Paragraph 0059-0062; 0103-0110
(2020/02/07)
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- A four-phenyl porphine preparation method
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The invention discloses a preparation method of meso-tetraphenylchlorin. The preparation method comprises the steps that 1, a mixed solution of pyrrole and aromatic aldehyde is prepared for standby; 2, a solvent is added into a polymerization reactor, nitrogen displacement is conducted till the concentration of tail oxygen is lower than 1%, the solvent is heated to backflow, the mixed solution obtained in the first step starts to be dropwise added, a reaction is started, after the mixed solution is dropwise added completely, the reaction is continuously conducted for 0.05 h to 0.5 h, and then the reaction is stopped; 3, oxygen-containing gas with the oxygen volume fraction ranging from 5% to 100% is fed into the polymerization reactor for oxidation, cooling is conducted after the oxidation is completed, filtration is conducted to obtain a filter cake and filtrate, and a product is obtained after the filter cake is washed and dried. The preparation method of the meso-tetraphenylchlorin has the advantages that the yield is high, safety and environmental protection are achieved, separation and purification are easy, and the product quality is stable.
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Paragraph 0060; 0110-0116
(2018/03/26)
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- Synthesis of amphiphilic meso -tetrasubstituted porphyrin-L-amino acid and -heterocyclic conjugates based on m -THPP
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Two series of amphiphilic meso-tetrasubstituted porphyrin conjugates based on 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin (m-THPP) covalently linked to L-amino acids and heterocycles were synthesized efficiently in the context of a program targeting new photosensitizers for PDT. 5,10,15-Tris(3-hydroxyphenyl)-20-(3-oxyacetic acid)phenyl]porphyrin and the respective trihexyl ether derivatives were conjugated with polar and non-polar natural L-amino acids such as glycine, L-proline, and L-tyrosine via an amide bond linker using N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate in diisopropylethylamine (HBTU/DIPEA). m-THPP was also conjugated with heterocyclic systems such as indole 3-acetic acid, 4-methylthiazole-5-carboxylic acid, and thiophene-2-carboxylic acid via ester linker using N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride in N-hydroxysuccinamide or 1-hydroxybenzotriazole (EDCI, NHS or HOBt). The members of the two series were obtained in good yields and characterized by UV-vis, HRMS MALDI-TOF, 1H NMR and 13C NMR spectroscopy.
- Sweed, Ayman M. K.,Senge, Mathias O.,Atta, Sanaa M. Sh.,Farrag, Dalia S.,Abdel-Rahman, Abdel-Rahman H.,Shaker, Yasser M.
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p. 997 - 1009
(2018/09/12)
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- The coulometric approach to the superoxide scavenging activity determination: The case of porphyrin derivatives influence on oxygen electroreduction
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The electrochemical and antioxidant properties of 5,10,15,20-tetrakis(3′-hydroxyphenyl)porphyrin (H2T(m-OHPh)P) and 5,10,15,20-tetrakis(4′-hydroxyphenyl)porphyrin (H2T(p-OHPh)P) were tested by the cyclic voltammetry (CV) method. It i
- Kuzmin, Sergey M.,Chulovskaya, Svetlana A.,Parfenyuk, Vladimir I.
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p. 1053 - 1062
(2015/10/29)
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- Ecofriendly Porphyrin Synthesis by using Water under Microwave Irradiation
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Water, under microwave irradiation and at a temperature of 473 K, reaches pressures above 16 bar, being capable to act as catalyst, without the use of organic solvents and oxidants, for meso-substituted porphyrin synthesis. Sustainability of the reaction is proved by E Factor=35 and EcoScale value of 50.5, the highest so far obtained for porphyrin synthesis. Methodology's wide versatility is clearly demonstrated by the good yields obtained for both aryl and alkyl substituted porphyrins. These reaction conditions represent a huge development, not only by using very high concentrations, minimizing organic solvent usage, but also by eradicating toxic expensive solvents and oxidants.
- Henriques, César A.,Pinto, Sara M.A.,Aquino, Gilberto L.B.,Pineiro,Calvete, Mário J.F.,Pereira, Mariette M.
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p. 2821 - 2824
(2015/03/30)
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- Photodynamic therapy efficacy enhanced by dynamics: The role of charge transfer and photostability in the selection of photosensitizers
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Progress in the photodynamic therapy (PDT) of cancer should benefit from a rationale to predict the most efficient of a series of photosensitizers that strongly absorb light in the phototherapeutic window (650-800 nm) and efficiently generate reactive oxy
- Arnaut, Luis G.,Pereira, Mariette M.,Dabrowski, Janusz M.,Silva, Elsa F. F.,Schaberle, Fabio A.,Abreu, Artur R.,Rocha, Luis B.,Barsan, Madalina M.,Urbanska, Krystyna,Stochel, Grazyna,Brett, Christopher M. A.
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supporting information
p. 5346 - 5357
(2014/05/20)
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- Simple porphyrin desymmetrization: 5,10,15,20-tetrakis(3-hydroxyphenyl) porphyrin (mTHPP) as a gateway molecule for peripheral functionalization
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The rise in the demand of unsymmetrical porphyrin systems for applications such as photodynamic therapy and nonlinear optics mandates a concomitant development of simple and practical synthetic approaches. A new method for the rapid generation of unsymmetrical porphyrins from the same common and easily accessible symmetric porphyrin starting material is discussed herein. A library of unsymmetric mTHPP [5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin] derivatives were synthesized in good yields through simple nucleophilic substitution, esterification, and metal-catalyzed cross-coupling reactions. This method was optimized to generate a library of customized unsymmetrical porphyrins quickly for use in a variety of applications. A common meso-aryl-substituted porphyrin as the starting material was used to update the synthetic toolkit through a mixture of classical and modern chemistry. This approach was studied as an approach to the synthesis of picket fence porphyrin mimics and afforded such compounds in good yields with few synthetic steps. In addition, employing simple nucleophilic substitution chemistry was employed to access cofacial caged bis(porphyrin) systems in two synthetic steps. Copyright
- Rogers, Luke,Burke-Murphy, Emeralda,Senge, Mathias O.
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p. 4283 - 4294
(2014/07/21)
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- MnO2 instead of quinones as selective oxidant of tetrapyrrolic macrocycles
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Porphyrins and chlorins were generated through dehydrogenation of the corresponding porphyrinogen and bacteriochlorin precursors using activated manganese dioxide and focused microwave irradiation. The application of this inexpensive heterogeneous oxidant under microwave heating conditions, instead of the quinones usually employed in conventional methodologies, allowed short reaction times, simple overall work-ups and good yields.
- Nascimento, Bruno F.O.,Rocha Gonsalves, António M.d'A.,Pineiro, Marta
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experimental part
p. 395 - 398
(2010/06/12)
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- Immobilization of porphyrinatocopper nanoparticles onto activated multi-walled carbon nanotubes and a study of its catalytic activity as an efficient heterogeneous catalyst for a click approach to the three-component synthesis of 1,2,3-triazoles in water
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An efficient, regioselective, one-pot and two-step synthesis of β-hydroxy 1,4-disubstituted 1,2,3-triazoles from a wide range of non-activated terminal alkynes and epoxides and sodium azide by way of a three-component click reaction using a catalytic amount of [meso-tetrakis(o- chlorophenyl)porphyrinato]copper(II) (5 mol%) in excellent isolated yields is described. The reactions were performed in water as a green solvent at ambient temperature without any additives. By performing two reaction steps in one pot and purifying only at the final step, this procedure excludes any interim purification of in situ generated organic azide intermediates, which significantly improves the overall yield and reduces the reaction time. To benefit from the recovery and reuse of the catalyst, a new heterogeneous catalyst was prepared by simple and successful impregnation of the catalyst onto activated multi-walled carbon nanotubes (AMWCNT). The heterogeneous catalyst was characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), atomic forced microscopy (AFM), and thermogravimetric (TG) analysis to estimate the amount of nitrogen adsorption, and Raman and FT-IR spectroscopy. Leaching experiments after ten successive cycles showed that the catalyst is most strongly anchored to the AMWCNT support. Mechanistically, porphyrinatocopper catalyzes each step of the reaction in different ways as a bifunctional catalyst including epoxide ring opening by azide delivery to epoxide, forming in situ generated 2-azido alcohols followed by activation of the C≡C triple bond of the starting terminal alkynes by forming a porphyrinatocopper-acetylide intermediate and thereby promoting the [3+ 2]-cycloaddition reaction as the key step to form the triazole framework.
- Sharghi, Hashem,Beyzavi, Mohammad Hassan,Safavi, Afsaneh,Doroodmand, Mohammad Mahdi,Khalifeh, Reza
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experimental part
p. 2391 - 2410
(2009/12/29)
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- Cooperativity in multiply H-bonded complexes
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The free energy of complexation of supramolecular complexes containing phenol-carbamate H-bonds is an additive function of the number of H-bonds, with a constant increment of 6 kJ mol-1 per interaction in carbon tetrachloride.
- Hunter, Christopher A.,Ihekwaba, Ndidi,Misuraca, Maria Cristina,Segarra-Maset, Maria Dolores,Turega, Simon M.
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supporting information; experimental part
p. 3964 - 3966
(2010/01/06)
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- NOVEL USES
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The invention provides the use of a compound of Formula (I), or metallated derivative thereof, in the preparation of a medicament for killing or attenuating the growth of microorganisms by a method which does not comprise exposing the compound to a photod
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Page/Page column 67-68
(2008/06/13)
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- NOVEL COMPOUNDS AND USES THEREOF
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A compound of formula (I): wherein X1, X2, X3, X4, Y1, Y2, Y3, Y4 and Z have meanings given in the description, and metallated forms of such compounds, which are usefu
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- Porphyrin synthesis in surfactant solution: Multicomponent assembly in micelles
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A synthesis of meso-substituted porphyrins in anionic sodium dodecyl sulfate micelles has been developed. Polar, functionalized aromatic aldehydes condense reversibly with pyrrole in the micellar phase. Oxidation of the porphyrinogen then provides functionalized porphyrins in yields of 10-48%. Hydrophobic aldehydes condense irreversibly to give low yields at practical substrate concentrations. Synthesis in D2O solution results in per-β-deuterated porphyrins. A two-phase model is used to rationalize the dependence of porphyrin yield on reactant and surfactant concentration. Micelles are viewed as potential wells which promote porphyrinogen assembly by binding products more tightly than reactants.
- Bonar-Law, Richard P.
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p. 3623 - 3634
(2007/10/03)
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- SYNTHESIS OF TETRAPHENYLPORPHINS WITH REACTIVE GROUPS IN THE BENZENE RINGS. 3. USE OF DIAZOTATION FOR THE PREPARATION OF SUBSTITUTED TETRAPHENYLPORPHINS
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Diazotization of tetra(aminophenyl)porphins has been employed to obtain halo- and hydroxy-tetraphenylporphins.Azo-coupling of tetra(diazophenyl)porphins has given isomeric tetraporphins.
- Semeikin, A.S.,Koifman, O.I.,Berezin, B.D.
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p. 397 - 401
(2007/10/02)
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- Synthesis of Tetraphenylporphins with Active Groups in the Phenyl Rings. 2. Preparation of Tetrakis(hydroxyphenyl)porphins
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The corresponding tetrakis(hydroxyphenyl)porphins were obtained by demethylation of tetrakis(methoxyphenyl)porphins with aniline hydrochloride or 60percent HBr.
- Semeikin, A. S.,Koifman, O. I.,Berezin, B. D.,Syrbu, S. A.
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p. 1082 - 1084
(2007/10/02)
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