Über einige neue Derivate des Perylens

Preparation and purification of some oxidation products of perylene

“…One gram (0.004 mole) of perylene (reagent grade) was oxidized with chromic acid (10 g of chromium trioxide in 100 ml of water) for 6 hr at 100°C with continuous agitation, according to a published procedure [4]. The mixture was filtered while hot, and the filtrate was saved for isolation of compound 8.…”

“…The carbon (containing adsorbed dione) was filtered off, washed with acetic acid, dried at 50°C, and extracted with 5 ml of warm nitrobenzene_ The extract was kept at room temperature for 1 to 2 hr; compound 2 crystallized as lightyellow needles; 30 mg (20%), mp 390 to 392°C (dec.); lit. mp 350°C [4]. This material produced one sharp, yellow spot having a strong, purple-pink fluorescence on a thin-layer chromatogram with 18: Analytically pure 3,10-perylenequinone is difficult to obtain by fractional recrystallization.…”

“…Anthraquinone-l ,5-dicarboxylic Acid (8) 5.1. Discussion Anthraquinone·l,5-dicarboxylic acid (8) [7] may be prepared by oxidation of perylene or 3,10-perylenequinone with chromic acid [4,8]; or by oxidation of 3,9'perylenequinone with chromic anhydride in sulfuric acid [9]; it may be characterized as its dimethyl ester [10].…”

“…3,1 O-Perylenequinone (2) 3.1. Discussion 3,1O-Perylenequinone (2) may be prepared by oxidation of perylene with chromic acid according to the method of Zinke and Unterkreuter [4]. Dione 2 is rather difficult to purify by recrystallization.…”

Synthesis, Photophysical Properties, and Nanocrystal Formation of a New Class of Tetra‐N‐Substituted Perylenes

“…[1][2][3] There are very few examples of tetra-N-substituted perylenes to be found in the literature to date which is because of the cumbersome nature of the established preparative methods. [4] We recently discovered a novel and efficient route to 4,9-diaminoperylenequinone-3,10-diimines [5] and showed that it is possible to convert these quinoidal systems to the reduced 3,4,9,10-tetraaminoperylenes, [6] a class of compounds which has very recently been cited in the patent literature of photovoltaic devices. [7] However, these tetraaminoperylenes have extremely negative redox potentials, which leads to their instantaneous reoxidation when exposed to air and makes them impossible to manipulate under the conditions normally encountered in dye chemistry.…”