33955-44-1

Usage

Heterocyclic compound

A compound containing a ring structure with at least one atom other than carbon, in this case, a perylenoquinone core structure.

Perylenoquinone core structure

A central ring structure with fused pentagons and a ketone group (C=O) attached to the 3,4-positions of the ring.

Bright yellow to orange solid

The physical appearance of the compound, indicating its suitability as a dye.

Used as a dye for textiles and inks

Indicates the compound's industrial applications and its ability to produce vibrant colors with high lightfastness.

Under study for potential use as an organic semiconductor

Suggests the compound's potential use in electronics due to its charge transport properties.

Charge transport properties

The ability of a material to move electrical charges, making it a candidate for use in organic electronic devices.

Potential use in organic electronic devices

Suggests the compound's potential applications in devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics.

Demonstrated anti-cancer properties in laboratory studies

Indicates the compound's potential applications in medicine and its ability to inhibit cancer cell growth.

Versatile compound

Highlights the range of potential industrial and scientific applications for 1H-Perylo[3,4-cd]pyridine-1,3(2H)-dione.

InChI:InChI=1/C22H11NO2/c24-21-16-9-7-14-12-5-1-3-11-4-2-6-13(18(11)12)15-8-10-17(22(25)23-21)20(16)19(14)15/h1-10H,(H,23,24,25)

Upstream product

• 33955-42-9 perylene-3,4,9,10-tetracarboxylic-3,4-anhydride-9,10-carboxamide 

Relevant academic research and scientific papers

A two-step synthesis of quaterrylenetetracarboxylic bisimides-novel NIR fluorescent dyes

Quaterrylenetetracarboxylic bisimides are prepared from perylene-3,4:9, 10-tetracarboxylic bisanhydride via perylene-3,4-dicarboxylic imides which are dimerized in molten alkali. The unsubstituted bisimide is an insoluble black pigment. N-substitution with the solubility-increasing 1-hexylheptyl group gives a soluble dye with a remarkably strong fluorescence in the NIR region (816 nm).

Perylene derivatives and their application as dispersants

The present invention relates to substituted perylene derivatives in which the substituent has a sterically stabilizing and/or electrostatically stabilizing effect. The perylene derivatives of the invention are particularly suitable as pigment dispersants. The present invention additionally relates to pigment preparations in which the perylene derivatives of the invention are used.

Preparation of perylene-3, 4-Dicarboxylic acid anhydrides

Preparation of perylene-3,4-dicarboxylic acid anhydrides of the general formula I STR1 wherein R1, R2, R3 and R4 can each be independently of one another hydrogen, halogen, C1 -C20 alkyl, C3 -C14 cycloalkyl, C1 -C20 alkoxy, phenyl, phenyloxy or phenylthio, where phenyl can in each case be mono- or polysubstituted by halogen, C1 -C20 alkyl, C3 -C14 cycloalkyl and/or C1 -C20 alkoxy; --NR52 or --OR5, wherein R5 is hydrogen or C1 -C20 alkyl, or one of the pairs R1 /R2 and R3 /R4 each in 6,7- or 1,12-position is a bridge having the bridge atoms or bridge atom groups --O--, --S--, S=O, SO2 or --NR6, wherein R6 is hydrogen, C1 -C20 alkyl or C3 -C14 cycloalkyl, by treating a perylene-3,4-dicarboximide of formula II STR2 (a) in a first step with a base and, (b) in a second step, reacting the resultant anion with an alkylation agent R7 --X, X being halogen and R7 being unsubstituted or phenyl-substituted C1 -C20 alkyl, to the corresponding carboximide and, (c) in a third step, treating the alkylated carboximide first with a base and, after the treatment with a base, obtaining the perylene-3,4-dicarboxylic acid anhydride I by acidifying the reaction mixture, and novel perylene-3,4-dicarboxylic acid anhydrides, novel N-alkylperylene-3,4-dicarboxylic acid imides and possibilities for the application of the compounds prepared according to this invention.

Preparation of perylene-3,4-dicarboxylic anhydrides

A process for forming perylene-3, 4-dicarboxylic anhydrides by reacting a corresponding perylene-3,4:9, 10-tetracarboxylic dianhydride with a sterically hindered amine, as a base, at an elevated temperature.