Aromatic−Aromatic Interaction between 2,3,5-Triphenyl-2H-tetrazolium Chloride and Poly(sodium 4-styrenesulfonate)

Abstract

Aromatic-aromatic interactions are found between the cationic molecule 2,3,5-triphenyl-2H-tetrazolium chloride (TTC) and the molecule poly(sodium 4-styrenesulfonate) (PSS) which makes the overall interaction of TTC with PSS more intense than the interaction with other polyanions containing sulfonate groups and produces a decrease on the redox ability of TTC. Diafiltration was used to compare the binding of TTC to PSS, poly(sodium vinylsulfonate) (PVS), and the more hydrophobic poly(sodium 2-(N-acrylamido)-2-methyl-propanesulfonate) (PAMPS). The UV-vis spectrum of TTC is changed in the presence of the aromatic polyanion. The 1H NMR signals of TTC are broadened and shifted in the presence of PSS, suggesting the occurrence of pi-pi interactions. Moreover, nuclear Overhauser effects (NOE) between the TTC and PSS protons are found. Possible structures for the complex are proposed.

Binding of Methylene Blue to Polyelectrolytes Containing Sulfonate Groups

“…We have already reported the high ability of this polymer to bind aromatic cations or zwitterions, due to a suitable complementation of short-range electrostatic forces, nonspecific hydrophobic interactions, and ar/ar interactions. [28][29][30][31][32][33] UV-Vis analyses show that in the presence of small amounts of PSS, the aggregation of MB is also induced in the environment of the polymer, as can be seen in Figure 7 by the disappearance of the monomer band. But as the concentration of PSS increases from an equimolar ratio (in sulfonate groups), the band corresponding to the higher aggregates shifts continuously to 616 nm, revealing the continuous formation of smaller aggregates.…”

“…Thus, the luminescent, [28][29][30] redox, [31] acid/base, [29,30,32] and binding properties [29][30][31]33] of various substrates are modified by this method. Ar/ar interactions are one of the principal noncovalent forces governing molecular recognition and biomolecular structure.…”

Extraction-spectrophotometric and theoretical (Hartree-Fock) investigations of a ternary complex of iron(II) with 4-nitrocatechol and 2,3,5-triphenyl-2H-tetrazolium

“…The results showed that the extracted ternary complex has a composition of 1 : 1 : 2 (Fe-4NC-TTC). One can conclude that the Fe(II)-4NC anionic chelate has a double negative charge, since TTC forms monovalent cation (TT + ) [13,[15][16][17][18][19][20][21][22][23][24][25][26] and the Fe(II)-to-TTC molar ratio is 1 : 2 ( Fig. 5, 2).…”

“…We previously reported [13] a liquid-liquid extraction-chromogenic system containing Fe(III), 4NC, and a widely used [15][16][17][18][19][20][21][22][23][24][25][26] cationic ion-association reagent, 2,3,5-triphenyl-2H-tetrazolium chloride (TTC). The next step, study of a similar system containing Fe(II) instead of Fe(III), is accomplished here.…”

Facile Formation of Redox‐Active Totally Organic Nanoparticles in Water by In Situ Reduction of Organic Precursors Stabilized through Aromatic–Aromatic Interactions by Aromatic Polyelectrolytes

“…Among aromatic counterions, the tetrazolium salt 2,3,5‐triphenyl‐2 H ‐tetrazolium chloride (TTC) has been used . It was seen by diafiltration and 1 H‐NMR, that aromatic–aromatic interactions between the tetrazolium salt and polymers bearing BS groups occur, and the strength of the interaction directly correlates with the linear aromatic density.…”