Pyrene-3-sulfonic acid

This procedure is based on the method of Smith, Opie, Waw-zonek, and Prichard3 for the preparation of 2,3,6-trimethyl-phenol. 3-Hydroxypyrene has been prepared by fusion of pyrene-3-sulfonic acid with sodium hydroxide 4 and by desul-fonation of 3-hydroxypyrene-5,8,10-trisulfonic acid with hot, dilute sulfuric acid.5... 

In a simulated atmosphere, direct epoxidation by ozone led to the formation of benzo[a]pyrene-4,5-oxide. Benzo [a] pyrene reacted with benzoyl peroxide to form the 6-benzoyloxy derivative (quoted, Nikolaou et al, 1984). It was reported that benzo [a] pyrene adsorbed on fly ash and alumina reacted with sulfur dioxide (10%) in air to form benzo[a]pyrene sulfonic acid (Nielsen et al., 1983). Benzo [a] pyrene coated on a quartz surface was subjected to ozone and natural sunlight for 4 and 2 h, respectively. The compounds 1,6-quinone, 3,6-quinone, and the 6,12-quinone of benzo[a]pyrene were formed in both instances (Rajagopalan et al., 1983). 

The lifetime of PN++ is much enhanced on the anionic NaLS and silica particles compared to water. An interesting feature of the silica particles is that PN++ is easily observed, hut unlike micelles or water e-g n is not observed. This is not due to the fact that e g reacts with silica, as e aq produced in the water bulk by photo-ionization of pyrene sulfonic acid (this molecule does not well bind to silica), has a long lifetime,... 

Table I shows the effect of various systems such as micelles, swollen micelles (achieved by adding hexanol to CTAB), microemulsion systems, vesicles formed from a double-chain CTAB surfactant, and reversed micelles with water cores formed with benzyl dimethylcetylammonium bromide in benzene. Hie active chromophore exists either as pyrene, pyrene sulfonic acid or pyrene tetrasulfonlc acid. Essentially the concept here is that the polar derivatives of pyrene will always locate pyrene at the surface of the micelle as these anionic species of pyrene complex with the positively charged surface. Dimethylaniline is used as an electron donor in each case, it can be seen that for pyrene, a continual decrease in the yield of the pyrene anion (ion yield of unity in the micelle) is observed on going from micelle to swollen micelle, to microemulsion, and no yield of ions is observed in a reversed micelle system. With pyrene tetrasulfonic acid the yield of ions over the different systems is fairly constant, even across to the reverse micellar system. However, the lifetime of the ions is extremely short in the reversed micellar system. An explanation for such behavior can be given as follows as we transverse across the...

Hence, the exiplex has a sandwich structure which promotes efficient back e transfer at the water pool, and the ion yield is very small. However, a sandwich reactant pair of this sort is not formed on a micelle surface and back reaction is slower than the escape of the cation from the surface. Hie swollen micelle and microemulsion systems lead to both randomly organised ionic products and sandwich pairs, to varying extents, which are reflected in the observed yield of ions, with polar derivatives of pyrene, e.g. pyrene sulfonic acid, etc., the reactants are kept on the assembly surface where reaction occurs, giving rise to ions from a non-sandwiched type of configuration. In the reverse micellar system, these ions although they are formed, nevertheless have a short lifetime, as they cannot escape to any great distance in the small water pool. Huts, micelles are far superior to microemulsions in various aspects of... 

Dyes, Dye Intermediates, and Naphthalene. Several thousand different synthetic dyes are known, having a total worldwide consumption of 298 million kg/yr (see Dyes AND dye intermediates). Many dyes contain some form of sulfonate as —SO H, —SO Na, or —SO2NH2. Acid dyes, solvent dyes, basic dyes, disperse dyes, fiber-reactive dyes, and vat dyes can have one or more sulfonic acid groups incorporated into their molecular stmcture. The raw materials used for the manufacture of dyes are mainly aromatic hydrocarbons (67—74) and include ben2ene, toluene, naphthalene, anthracene, pyrene, phenol (qv), pyridine, and carba2ole. Anthraquinone sulfonic acid is an important dye intermediate and is prepared by sulfonation of anthraquinone using sulfur trioxide and sulfuric acid. 

Chemical/Physical. At room temperature, concentrated sulfuric acid will react with pyrene to form a mixture of disulfonic acids. In addition, an atmosphere containing 10% sulfur dioxide transformed pyrene into many sulfur compounds, including pyrene-1-sulfonic acid and pyrenedisulfonic acid (Nielsen et al., 1983). 

Lateral Mobility(Fluidity) of Sulfonate A and B Micelles. The ratio of excimer to monomer fluorescence intensity of pyrene had previously been used to measure the fluidity of biological membranes (8). The ease of excimer formation was correlated with the fluidity of the membrane. The same principle may be applied to the measurement of fluidity in inverted micelles. To this end, we used three pyrene carboxylic acid probes of varying chain length PVA, PNA and... 

N -Iodoacetylethylenediamiwo)-naphthalene-1-sulfonic acid N-(Iodoacetylaminoethyl)-5-naphthylamine-1-sulfonic acid N-(lodoacetylaminoethyl)-8-naphthylamine-l-sulfonic acid 7-(p-Methoxybenzylamino-4-nitro-benz-2-oxy-1,3-diazole N-3-Pyrene maleimide Quinacrine mustard Rhodamine B isothiocyanate... 

Anthracene or pyrene or anthraquinone 2-sulfonic acid or pyrene 1-sulfonic acid p,p -Diisocyanatodiphenylmethane, triisocyanate, THF, bis-phenol A, 1,3,5-trihydroxybenzene Fluorescence sensor [129]... 

Metal salts such as sodium and ammonium sulfate exert a dilution effect that effectively weakens the aggressive action of sulfuric acid. Thus, Tietze and Bayer,159 sulfonating pyrene in the presence of sodium sulfate, weakened the oxidizing action of the pure acid on this hydrocarbon in fact, heating pyrene, sulfuric acid, and sodium sulfate in the molar proportions 1 3 3 at 180° for 6 hours gives a 100% yield of 1-pyrenesulfonic acid.160 Adding sodium sulfate is also advantageous in preparation of l-aminoanthraquinone-2-sulfonic acid.161... 

Similarly, l-anilinonaphthalene-8-sulfonic acid (ANS) only emits in a hydrophobic environment, being almost completely quenched in aqueous solution. ANS and some other dyes, including 6-(p-toluidinyl)naphthalene-2-sulfo-nate, pyrene, l,6-diphenyl-l,3,5-hexatriene, fluorescein, and rhodamine derivatives attached to long acyl chains or to fatty acids that localize in the cellular membranes were used as probes for hydrophobic sites in proteins, protein folding, imaging of membranes of the cell, and solvent polarity. Pyrene-labeled fatty acids were used to detect the fusion of two membranes. When present in a membrane at sufficiently high concentrations, pyrene excimers (excited-state dimers) are formed that emit at 470 nm. Upon fusion with other membranes, probe concentration decreases, and excimer fluorescence is replaced by monomer fluorescence at 400 nm. This process can be monitored by ratiometric detection of pyrene labels. 

Spectral position and form of fluorescence bands are dependent on the molecular environment (neighbored molecules) and can be used to investigate adsorption, complexation, interaction, or aggregation processes. Special fluorophores like pyrene and l-anilinonaphthalene-8-sulfonic acid (ANS) exhibit dramatic changes of their fluorescence spectra when changing the polarity of their environment and were therefore often applied as fluorescence probes. 

Benzophenone sunscreen agents, 119 Benzo[a]pyrene, 97, 99 Benzo[a]pyrene triols, 99, 231 Benzo[/)]quinoline, 347 Benzothiazole, 340 Benzosuberone-4-sulfonic acid, 270 2-Benzothiazole-2,2 -disulfide, 124 5-Benzoyl-2-acctylthiophene, 255 Benzpylecgonine, 312i, 492 5-Benzoyl-2-ethylthiophene, 255 Benzoylmercury, 93 Benzoylnorecgonine, 312... 

Pyrene 46 reacts with chlorosulfonic acid (two equivalents) in 5ym-tetrachlor-oethane (10-20 °C) for 15-20 hours to yield the 3-sulfonic acid (90-92%). ... 

Tietze, E. Bayer, O. Sulfonic acids of pyrene and their derivatives. Justus Liebigs Ann. Chem. 1939, 540,189-210. 

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