Synthesis and properties of water-soluble porphyrins bearing multidentate ligands

2004 ◽  
Vol 08 (08) ◽  
pp. 1047-1054 ◽  
Author(s):  
Yoshio Uemori ◽  
Masato Sakurai ◽  
Atsuko Osada ◽  
Hiroki Munakata ◽  
Hiroyasu Imai ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Aromatic Compounds ◽  
Covalent Binding ◽  
Nitrilotriacetic Acid ◽  
Association Constants ◽  
Water Soluble ◽  
Para Position ◽  
Multidentate Ligands ◽  
Acid Base ◽  
Base Properties

Water-soluble porphyrins bearing multidentate ligands were prepared by covalent binding of nitrilotriacetic acid to 5,10,15,20-tetrakis(4-aminophenyl)porphyrin or three atropisomers of 5,10,15,20-tetrakis(2-aminophenyl)porphyrin. The acid-base properties and monomer-dimer behavior of the porphyrins were affected by the positions of the multidentate ligands with respect to the porphyrin plane. Among the porphyrins, the porphyrin bearing multidentate ligands at the para position of the phenyl groups dimerized in an aqueous solution. The association constants of the porphyrins with various aromatic compounds were studied in water at pH 7.4 containing 10 mM HEPES at 25°C. These values varied with the structure and charges of both the porphyrins and the aromatic compounds. The association constants of the porphyrin bearing multidentate ligands at the 2-position of the phenyl groups were small compared to those of the porphyrin bearing multidentate ligands at the 4-position.

Synthesis, Acid-Base Properties, Kinetics and Mechanism of Cu2+ Incorporation into Water-Soluble Highly Substituted Porphyrins

2017 ◽  
Vol 21 (09) ◽  
pp. 611-621
Author(s):  
Hirofumi Konno ◽  
Jun Takeda
Keyword(s):  
Aqueous Solution ◽  
Ionic Strength ◽  
Kinetics And Mechanism ◽  
Water Soluble ◽  
Acid Base ◽  
Base Equilibrium ◽  
Absorbance Change ◽  
Acid Base Equilibrium ◽  
Kinetics Of ◽  
Base Properties

The synthesis, acid-base properties, and kinetics of Cu[Formula: see text] incorporation into water-soluble highly substituted porphyrins were studied. The basicity increased and the stepwise acid-base equilibrium was clarified by increasing the number of phenyl groups at the [Formula: see text] position, and the basicity of a dodeca-substituted porphyrin increased with the ionic strength. The metalation reaction of the dodeca-substituted porphyrin with Cu[Formula: see text] in aqueous solution revealed a biphasic absorbance change at 453 nm. Plots of [Formula: see text] or[Formula: see text] vs. the Cu[Formula: see text] concentration and of log ([Formula: see text] or[Formula: see text]/[Formula: see text] 0) vs. the ionic strength show that [Formula: see text] is dependent on the Cu[Formula: see text] concentration and ionic strength, while [Formula: see text] is independent of these parameters. These results confirm the stepwise metalation mechanism and the existence of an intermediate in aqueous solution, which is indicated by the biphasic absorbance change at 453 nm.

Enantioselective Recognition of Chiral Guests by the Water-Soluble Chiral Keplerate {Mo132} Spherical Capsule with 30 Inner Lactate Ligands

2019 ◽  
Author(s):  
Nancy Watfa ◽  
Weimin Xuan ◽  
Zoe Sinclair ◽  
Robert Pow ◽  
Yousef Abul-Haija ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Chiral Recognition ◽  
Association Constants ◽  
Water Soluble ◽  
Enantioselective Recognition ◽  
H Nmr ◽  
Dosy Nmr ◽  
Spherical Capsule ◽  
Surface Pores ◽  
Guest Chemistry

Investigations of chiral host guest chemistry are important to explore recognition in confined environments. Here, by synthesizing water-soluble chiral porous nanocapsule based on the inorganic metal-oxo Keplerate-type cluster, {Mo<sub>132</sub>} with chiral lactate ligands with the composition [Mo<sub>132</sub>O<sub>372</sub>(H<sub>2</sub>O)<sub>72</sub>(<i>x-</i>Lactate)<sub>30</sub>]<sup>42-</sup> (<i>x</i> = D or L), it was possible to study the interaction with a chiral guest, L/D-carnitine and (<i>R</i>/<i>S</i>)-2-butanol in aqueous solution. The enantioselective recognition was studied by quantitative <sup>1</sup>H NMR and <sup>1</sup>H DOSY NMR which highlighted that the chiral recognition is regulated by two distinct sites. Differences in the association constants (K) of L- and D-carnitine, which, due to their charge, are generally restricted from entering the interior of the host, are observed, indicating that their recognition predominantly occurs at the surface pores of the structure. Conversely, a larger difference in association constants (K<i><sub>S</sub></i>/K<i><sub>R</sub></i> = 3) is observed for recognition within the capsule interior of (<i>R</i>)- and (<i>S</i>)-2-butanol.

Acid–base properties and DNA-binding of water soluble N-confused porphyrins with cationic side-arms

2008 ◽  
Vol 6 (22) ◽  
pp. 4157 ◽  
Author(s):  
Yoshiya Ikawa ◽  
Shoji Moriyama ◽  
Hiroyuki Harada ◽  
Hiroyuki Furuta
Keyword(s):  
Dna Binding ◽  
Water Soluble ◽  
Acid Base ◽  
Base Properties

Toward novel sulphur-containing derivatives of tetraazacyclododecane: synthesis, acid–base properties, spectroscopic characterization, DFT calculations, and cadmium(ii) complex formation in aqueous solution

2020 ◽  
Vol 44 (20) ◽  
pp. 8337-8350 ◽  
Author(s):  
Marianna Tosato ◽  
Marco Verona ◽  
Riccardo Doro ◽  
Marco Dalla Tiezza ◽  
Laura Orian ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Complex Formation ◽  
Dft Calculations ◽  
Spectroscopic Characterization ◽  
Acid Base ◽  
Derivatives Of ◽  
Base Properties

New sulphur derivatives of cyclen, with potential complementary properties with respect to known compounds, have been synthesized and studied.

Acid-Base Properties of Peptide Peroxyl Radicals in Aqueous Solution

1989 ◽  
Vol 6 (2-3) ◽  
pp. 127-128 ◽  
Author(s):  
Oliver J. Mieden ◽  
Man Nien Schuchmann ◽  
Clemens Von Sonntag
Keyword(s):  
Aqueous Solution ◽  
Peroxyl Radicals ◽  
Acid Base ◽  
Base Properties

Synthesis of the tetranitro derivative of thiacalix[4]arene and its acid–base properties

2004 ◽  
Vol 82 (8) ◽  
pp. 1266-1270 ◽  
Author(s):  
Xiaojun Hu ◽  
Zhongliang Zhu ◽  
Tianxiang Shen ◽  
Xianfa Shi ◽  
Jie Ren ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Factor Analysis ◽  
Water Solution ◽  
Uv Spectroscopy ◽  
Nitro Derivative ◽  
Uv Absorption ◽  
Acid Base ◽  
Ph Distribution ◽  
Base Properties

The tetranitro derivative 3 of thiacalix[4]arene was synthesized and characterized. Its acid–base properties in water solution were studied by UV spectroscopy. The four pKa values of 3 were determined by target testing factor analysis (TTFA). The pure UV absorption curves and pH distribution curves of five forms of 3 presented in aqueous solution were also calculated by TTFA.Key words: thiacalixarene, nitro derivative, acid–base properties.

Acid-Base Properties of Adenosine 5′-O-Thiomonophosphate in Aqueous Solution

1997 ◽  
Vol 3 (1) ◽  
pp. 29-33 ◽  
Author(s):  
Bin Song ◽  
Roland K. O. Sigel ◽  
Helmut Sigel
Keyword(s):  
Aqueous Solution ◽  
Acid Base ◽  
Base Properties
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