Abstract:
Tert. alkylphenoxy substituted polycyclic compounds of general formula (I), in which the variables have the following meanings: P = a conjugated polycyclic group, optionally aryl substituted, stable to base and acid and not containing residues from the group -CO-NH-CO-, -COOH and -CO-O-CO-; R = C1-C8 alkyl, the carbon chain of which may be interrupted by one or several groups of -O-, -S-, -NR -, -CO- and/or -SO2- and which may be mono- or serially-substituted by C1-C6 alkoxy or a 5- to 7-membered heterocyclic group, bonded by means of a nitrogen atom, which can contain further heteroatoms and can be aromatic, C5-C8 cycloalkyl, the carbon skeleton of which may be interrupted by one or several groups of -O-, -S-, -NR -, -CO- and/or -SO2- and may optionally be substituted with C1-C6 alkyl; R = H or C1-C6 alkyl; Hal = chlorine and/or bromine; m = a number from 0 to 15; n = a number from 1 to 16, whereby the sum m + n
Abstract:
The invention relates to 9-cyano-substituted perylene-3,4-dicarboxylic acid monoimides (I) where the variables have the following meanings: X = a chemical bond, optionally substituted C1-C30 alkylenes, C5-C8 cycloalkylenes, arylenes, heteroarylenes, C1-C20 alkylarylenes, C1-C20 alkylheteroarylenes, aryl- or heteroaryl-C1-C20 alkylenes, Y = a functional group Y', or a polymerisable group P, or X-Y together = a group R, Y' = amino, hydroxy, -COOH, -SO3H, chlorine or bromine, P = a group (II), A, B independently = H, C1-C6 alkyl, phenyl, or together form a cyclopentene or cyclohexene ring, which comprise the double bond to which A and B are bonded, Q = a chemical bond, a -O-, -NR -, -S-, -OCO-, -OCOO-, -OCONR -, -NR CO-, -NR COO-, -NR CONR -, -CO-, -COO-, -CONR -, -SO2-O-, -SO2NR -, -O-SO2- or -NR SO2- group, n = 0, 1, 2 or 3 and R = H, optionally-substituted C1-C30 alkyl, C5-C8 cycloalkyl, aryl or heteroaryl.
Abstract:
Tert-alkylphenoxy-substituted polycyclic compounds of the general formula I where P is a conjugated polycyclic radical which is stable to bases and nucleophiles, optionally bears aryl substituents and contains no group from the group consisting of -CO-NH-CO-, -COOH and -CO-O-CO-; R is C 1 -C 8 -alkyl, whose carbon chain may be interrupted by one or more groups selected from the group consisting of -O-, -S-, -NR 1 -, -CO- and/or -SO 2 - and which may be monosubstituted or polysubstituted by C 1 -C 6 -alkoxy or by a 5- to 7-membered heterocyclic radical which is attached via a nitrogen atom and may contain further heteroatoms and be aromatic; C 5 -C 8 -cycloalkyl whose carbon chain may be interrupted by one or more groups selected from the group consisting of -O-, -S-, -NR 1 -, -CO- and/or -SO 2 - and which may be monosubstituted or polysubstituted by C 1 -C 6 -alkyl; R 1 is hydrogen or C 1 -C 6 -alkyl; Hal is chlorine and/or bromine; m is from 0 to 15; n is from 1 to 16, subject to the proviso that the sum m+n is
Abstract:
A process for converting perylene-3,4:9,10-tetracarboximides of the general formula I in which R1 and R2 are each unbranched, branched or cyclic C1-C8-alkyl to a form suitable for use as fluorescent dyes, which comprises a) dissolving or suspending the perylene-3,4:9,10-tetracarboximides whose molecules have a molecular volume of ≦̸230 Å3 in an organic or inorganic solvent at from 0 to 250° C., b1) cooling the solution obtained in step a) to or below the crystallization temperature and, in the case of an organic solvent, if desired at the same time removing excess solvent until the first crystals form, or, in the case of an inorganic solvent, adding water or dilute aqueous solutions of the solvent until the first crystals form, and maintaining the solution at this temperature for further crystallization or b2) cooling the suspension obtained in step a) to or below the crystallization temperature when the temperature in step a) was above the crystallization temperature, and maintaining the suspension at this temperature for further crystallization, c) isolating the solvate crystals formed in step b) and d) then removing the solvent from the solvate crystals, and also novel crystalline forms of perylene-3,4:9,10-tetracarboxylic diimides.
Abstract:
A process for preparing perylene-3,4:9,10-tetracarboxylic dianhydride, comprising: dimerizing a naphthalene-1,8-dicarboximide of the formula IIa; reoxidizing the resulting alkali metal salt of the leuco form of the perylene-3,4:9,10-tetracarboxylic diimide of the formula Ia; hydrolyzing the diimide to the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid in the presence of an inert organic solvent, of an alkali metal base and of water; and subjecting the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid to the action of an aqueous inorganic acid to convert it into perylene-3,4:9,10-tetracarboxylic dianhydride; wherein R3 is cyclohexyl or phenyl which may each be substituted by up to three C1-C4-alkyl radicals, and the dimerizing is in a substantially homogeneous reaction medium consisting essentially of an apolar aprotic organic solvent and an alkali metal base.
Abstract:
Tert-alkylphenoxy-substituted polycyclic compounds of the general formula I where P is a conjugated polycyclic radical which is stable to bases and nucleophiles, optionally bears aryl substituents and contains no group from the group consisting of -CO-NH-CO-, -COOH and -CO-O-CO-; R is C 1 -C 8 -alkyl, whose carbon chain may be interrupted by one or more groups selected from the group consisting of -O-, -S-, -NR 1 -, -CO- and/or -SO 2 - and which may be monosubstituted or polysubstituted by C 1 -C 6 -alkoxy or by a 5- to 7-membered heterocyclic radical which is attached via a nitrogen atom and may contain further heteroatoms and be aromatic; C 5 -C 8 -cycloalkyl whose carbon chain may be interrupted by one or more groups selected from the group consisting of -O-, -S-, -NR 1 -, -CO- and/or -SO 2 - and which may be monosubstituted or polysubstituted by C 1 -C 6 -alkyl; R 1 is hydrogen or C 1 -C 6 -alkyl; Hal is chlorine and/or bromine; m is from 0 to 15; n is from 1 to 16, subject to the proviso that the sum m+n is
Abstract:
A process for converting perylene-3,4:9,10-tetracarboximides of the general formula I in which R1 and R2 are each unbranched, branched or cyclic C1-C8-alkyl to a form suitable for use as fluorescent dyes, which comprises a) dissolving or suspending the perylene-3,4:9,10-tetracarboximides whose molecules have a molecular volume of ≦̸230 Å3 in an organic or inorganic solvent at from 0 to 250° C., b1) cooling the solution obtained in step a) to or below the crystallization temperature and, in the case of an organic solvent, if desired at the same time removing excess solvent until the first crystals form, or, in the case of an inorganic solvent, adding water or dilute aqueous solutions of the solvent until the first crystals form, and maintaining the solution at this temperature for further crystallization or b2) cooling the suspension obtained in step a) to or below the crystallization temperature when the temperature in step a) was above the crystallization temperature, and maintaining the suspension at this temperature for further crystallization, c) isolating the solvate crystals formed in step b) and d) then removing the solvent from the solvate crystals, and also novel crystalline forms of perylene-3,4:9,10-tetracarboxylic diimides.
Abstract:
A process for preparing perylene-3,4:9,10-tetracarboxylic dianhydride, comprising: dimerizing a naphthalene-1,8-dicarboximide of the formula IIa; reoxidizing the resulting alkali metal salt of the leuco form of the perylene-3,4:9,10-tetracarboxylic diimide of the formula Ia; hydrolyzing the diimide to the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid in the presence of an inert organic solvent, of an alkali metal base and of water; and subjecting the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid to the action of an aqueous inorganic acid to convert it into perylene-3,4:9,10-tetracarboxylic dianhydride; wherein R3 is cyclohexyl or phenyl which may each be substituted by up to three C1-C4-alkyl radicals, and the dimerizing is in a substantially homogeneous reaction medium consisting essentially of an apolar aprotic organic solvent and an alkali metal base.
Abstract:
Tert-alkylphenoxy-substituted polycyclic compounds of the general formula I where P is a conjugated polycyclic radical which is stable to bases and nucleophiles, optionally bears aryl substituents and contains no group from the group consisting of -CO-NH-CO-, -COOH and -CO-O-CO-; R is C 1 -C 8 -alkyl, whose carbon chain may be interrupted by one or more groups selected from the group consisting of -O-, -S-, -NR 1 -, -CO- and/or -SO 2 - and which may be monosubstituted or polysubstituted by C 1 -C 6 -alkoxy or by a 5- to 7-membered heterocyclic radical which is attached via a nitrogen atom and may contain further heteroatoms and be aromatic; C 5 -C 8 -cycloalkyl whose carbon chain may be interrupted by one or more groups selected from the group consisting of -O-, -S-, -NR 1 -, -CO- and/or -SO 2 - and which may be monosubstituted or polysubstituted by C 1 -C 6 -alkyl; R 1 is hydrogen or C 1 -C 6 -alkyl; Hal is chlorine and/or bromine; m is from 0 to 15; n is from 1 to 16, subject to the proviso that the sum m+n is