The synthesis and some physical properties of <i>ms</i>‐tetra(pentafluorophenyl)‐porphin and <i>ms</i>‐tetra(pentachlorophenyl)porphin

Longo, Frederick R.; Finarelli, Margaret G.; Kim, Jean B.

doi:10.1002/jhet.5570060625

Cited by 154 publications

(58 citation statements)

References 13 publications

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“…[25]. All the pyridyl-containing compounds (H2THP(mPyr)4, H2P(pPyr)4 and H2P(mPyr) 4) used for complexation of (ZnHTPP) 2 have been synthesized and purified according to known methods [26][27][28][29][30].…”

Section: Methodsmentioning

confidence: 99%

Formation and optical properties of self-organized pentameric porphyrin arrays

Chernook

Rempel

Borczyskowski

et al. 1996

Chemical Physics Letters

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Principles of formation, electronic absorption and fluorescence spectra are reported for self-organized pentameric arrays of tetrapyrrolic macrocycles. In these arrays two molecules of Zn-porphyrin dimers, Zn(II)l,4-bis [5-(10,15,20+tri-p-hexylphenylporphyrinyl)]-benzene ((ZnHTPP) 2) are bound via one molecule of a tetrapyridyl-substituted free base of porphyrin or tetrahydroporphyrin. The process of self-assembly is based on the twofold coordination of the central Zn ions !n the dimer with the nitrogen atoms of the pyridyl rings in the free base which is strong enough to make the complexes stable at room temperature. The formation of the complexes can be followed by changes in the absorption bands of (ZnHTPP) 2 characteristic of an axial extra-ligation of Zn-porphyrins with pyridine or pyridyl-substituted compounds. The spectral behavior of the free bases in the pentads is determined by a non-planar distortion of their macrocycle caused by the two-point binding with the dimers. The fluorescence intensity of the Zn-porphyrin dimer decreases essentially upon complexation with the tetrapyridyl-substituted free bases. This quenching effect is assigned to a singlet-silaglet energy transfer from the complexed Zn-porphyrin dimers to the free base subunit in the pentad.

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Section: Methodsmentioning

confidence: 99%

Formation and optical properties of self-organized pentameric porphyrin arrays

Chernook

Rempel

Borczyskowski

et al. 1996

Chemical Physics Letters

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“…Epichlorohydrin was from SD's Chemicals (Mumbai, India). Meso-tetra(4-sulphonatophenyl) porphyrinato zinc(II) (ZnTPPS), meso-tetra(4-sulphonatophenyl)-porphyrinato copper(II) (CuTPPS), meso-tetra (4-carboxyphenyl) porphyrinato zinc(II) (ZnTCPP), mesotetra (4-carboxyphenyl)porphyrinato copper(II) (CuTCPP), meso-tetra(4-methylpyridinium) porphyrinato zinc(II) (ZnTMPyP) and meso-tetra(4-methylpyridinium)porphyrinato copper (II) (CuTMPyP) were prepared and characterized as described previously [12][13][14][15][16].…”

Section: A T E R I a L S A N D M E T H O D S Materialsmentioning

confidence: 99%

Thermodynamic and kinetic analysis of porphyrin binding to Trichosanthes cucumerina seed lectin

et al. 2001

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The interaction of several metallo-porphyrins with the galactose-specific lectin from Trichosanthes cucumeirna (TCSL) has been investigated. Difference absorption spectroscopy revealed that significant changes occur in the Soret band region of the porphyrins upon binding to TCSL and these changes have been monitored to obtain association constants (K a ) and stoichiometry of binding (n ). The dimeric lectin binds two porphyrin molecules and the presence of the specific saccharide lactose did not affect porphyrin binding significantly, indicating that the sugar and the porphyrin bind at different sites. The K a values obtained for the binding of different porphyrins with TCSL at 25 8C were in the range of 2 Â 10 3 25 Â 10 5 M 21 . Association constants for meso-tetra(4-sulphonatophenyl)porphyrinato copper(II) (CuTPPS), a porphyrin bearing four negative charges and meso-tetra(4-methylpyridinium)porphyrinato copper(II) (CuTMPyP), a porphyrin with four positive charges, were determined at several temperatures; from the temperature dependence of the association constants, the thermodynamic parameters change in enthalpy (DH8) and change in entropy (DS8) associated with the binding process were estimated. The thermodynamic data indicate that porphyrin binding to TCSL is driven largely by a favourable entropic contribution; the enthalpic contribution is very small, suggesting that the binding process is governed primarily by hydrophobic forces. Stopped-flow spectroscopic measurements show that binding of CuTMPyP to TCSL takes place by a single-step process and at 20 8C, the association and dissociation rate constants were 1.89 Â 10 4 M 21 : s 21 and 0.29 s 21, respectively.

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“…The four atropisomers of meso-tetra(6 methyl-N-methyl-2-pyridyl) porphine were synthesized via standard procedures (16) by refluxing 3-methyl-2-pyridine carboxaldehyde (17) with pyrrole in propionic acid. Following workup, the four atropisomers were separated on silica gel using CH2C12/CH3OH as an The toluene-pyridinium series of compounds meso-a,B,7-tritolyl-6-(Nmethyl-4-pyridiniumyl)porphine, 1+, meso-a,B ditolyl-y,6-di(N-methyl-4-pyridiniumyl)porphine, cis-2+, meso-ac,r-ditolyl-Q,6-di(N-methyl-4-pyridiniumyl)porphine, trans-2+ and meso-a-tolyl-Q,y,6-tri(N-methyl-4-pyridiniumyl)porphine, 3+, were synthesized using the mixed aldehyde method (19).…”

Section: Synthesis Of the Compoundsmentioning

confidence: 99%

Cationic porphyrins as probes of DNA structure

1986

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The DNA binding specificity of a group of cationic manganese porphyrin complexes has been examined using DNase I footprinting methodology and by observing the sites of porphyrin-induced DNA strand scission in the presence of potassium superoxide.The compounds, which possess systematic changes in total charge, its distribution on the periphery on the macrocycle and ligand shape, bind in the minor groove of AT rich regions of DNA. While changes in total charge and charge arrangement do not significantly influence specificity, a shape change which blocks close ligand contact with the minor groove relaxes the original AT specificity causing the compound to cleave at both AT and GC sites. The observed changes in binding sequence specificity were interpreted in terms of electrostatic and steric factors associated with both the compounds and DNA.

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The synthesis and some physical properties of ms‐tetra(pentafluorophenyl)‐porphin and ms‐tetra(pentachlorophenyl)porphin

Cited by 154 publications

References 13 publications

Formation and optical properties of self-organized pentameric porphyrin arrays

Formation and optical properties of self-organized pentameric porphyrin arrays

Thermodynamic and kinetic analysis of porphyrin binding to Trichosanthes cucumerina seed lectin

Cationic porphyrins as probes of DNA structure

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