Perylene tetracarboxylic acid dianhydride

Several methods have been reported for the monofunctionaUzation of PDI [6] including one-pot imidization (route A) or a base-promoted coupling reaction between naphthalene monoimide derivatives (route B) [7], as shown in Scheme 2. We found the one-pot imidizatitMi reaction (route A) to be more practical than route B route B consisted of five steps and the open-form product 6b was labile under the basic reaction conditions required to produce the closed product 6a. The one-pot imidization, route A, was simple and 3 could easily be recovered via column chromatography because the use of an excess amount of 3 was necessary. Concerning the solubility and reactivity of perylene tetracarboxylic acid dianhydride (PDA) 4, the imidization of 4 was, first, carried out with 2,6-ditsopropylaniline (5) in imidazole then 3 in propionic acid solution was added to produce the closed product PDI 6a. 

Synthesis of Perylene Tetracarboxylic Acid Dianhydride (PTCA) by Hydrolysis of PTCI to PTCA, and PTCA as a Pigment (Pigment Red 224)... 

Dori N, Menon M, Kilian L, Sokolowski M, Kronik L, Umbach E (2006) Valence electronic structure of gas-phase 3,4,9,10-perylene tetracarboxylic acid dianhydride experiment and theory. Phys Rev B 73 195208... 

Perylene pigments include the dianhydride and diimide of perylene tetracarboxylic acid along with derivatives of the diimide while perinone pigments are derived from naphthalene tetracarboxylic acid. 

The primary starting material for the synthesis of perylene tetracarboxylic acid pigments is the dianhydride 71. It is prepared by fusing 1,8-naphthalene dicar-boxylic acid imide (naphthalic acid imide 69) with caustic alkali, for instance in sodium hydroxide/potassium hydroxide/sodium acetate at 190 to 220°C, followed by air oxidation of the molten reaction mixture or of the aqueous hydrolysate. The reaction initially affords the bisimide (peryldiimide) 70, which is subsequently hydrolyzed with concentrated sulfuric acid at 220°C to form the dianhydride ... 

The dianhydride of perylene tetracarboxylic acid is converted into the pigment form by preparing the corresponding alkali salt and then reprecipitating the compound with an acid. The dianhydride is formed after separating the acid by thermal aftertreatment at 100 to 200°C, possibly under pressure, with an organic solvent. The list of suitable media includes alcohols, ketones, carboxylic acid esters, hydrocarbons, and dipolar aprotic solvents. 

Synthesis of polyimides directly from perylene-3,4,9,10-tetracarboxylic acid dianhydride (DPTA) [4, 5] using diamines as the nucleophilic comonomers which leads to improved solubility for the target polymers. 

The name perylene pigments refers to a class of high performance pigments made up of N,N -disubstituted perylene-3,4,9,10-tetracarboxylic acid imides or perylene-3,4,9,10-tetracarboxylic acid dianhydride. 

Structural variation of perylenes can simply be accomplished by using different amine precursors. The chemical structures of various photoconductive perylenes (general structures XIX and XX) are shown in Table 10.8. Another approach is to modify the central perylene ring structure. Along this line, Duff et al. [238] showed that sulfonation of perylene-3,4,9,10-tetracarboxylic dianhydride with chlorosulfonic acid leads to the formation of perylene-l,12-sulfone-... 

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