WO2005070894A1 - Procede de fabrication de di-imides de l'acide terrylene-3,4:11,12-tetracarboxylique - Google Patents

Procede de fabrication de di-imides de l'acide terrylene-3,4:11,12-tetracarboxylique Download PDF

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WO2005070894A1
WO2005070894A1 PCT/EP2005/000314 EP2005000314W WO2005070894A1 WO 2005070894 A1 WO2005070894 A1 WO 2005070894A1 EP 2005000314 W EP2005000314 W EP 2005000314W WO 2005070894 A1 WO2005070894 A1 WO 2005070894A1
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alkyl
substituted
aryl
alkoxy
cyano
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PCT/EP2005/000314
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German (de)
English (en)
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Martin KÖNEMANN
Klaus MÜLLEN
Erik Reuther
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Basf Aktiengesellschaft
MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V.
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Priority to EP05700915A priority Critical patent/EP1713777A1/fr
Publication of WO2005070894A1 publication Critical patent/WO2005070894A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems

Definitions

  • the present invention relates to a new process for the preparation of terrylene-3,4: 11,12-tetracarboxylic acid diimides of the general formula I.
  • R, R ' are independently hydrogen; CrC 3 o-alkyl, the carbon chain of which can be interrupted by one or more groupings -O-, -S-, -NR 1 -, -CO- and / or -SO 2 - and by cyano, CrC 6 alkoxy, aryl , which can be substituted by CC 18 alkyl or -CC 6 alkoxy, and / or a 5- to 7-membered heterocyclic radical bonded via a nitrogen atom, which may contain further heteroatoms and may be aromatic, may be mono- or polysubstituted can; C 5 -C 8 cycloalkyl, the carbon skeleton of which is interrupted by one or more groupings -O-, -S- and / or -NR 1 - and / or which can be substituted one or more times by CrC 6 alkyl; Aryl or hetaryl, which is substituted by dC ⁇ alkyl, CC 6 alkoxy,
  • R 2 is hydrogen, -CC 18 alkyl; Aryl or hetaryl, each of which can be substituted by CC 6 alkyl, C r C 6 alkoxy, hydroxy, carboxy or cyano.
  • the invention further relates to processes for the preparation of 9- (dioxaborolan-2-yl) perylene-3,4-dicarboximides of the general formula IVa
  • R has the meaning already mentioned and the radicals R 3 are identical or different and independently of one another are hydrogen, C 1 -C 30 -alkyl, C 5 -C 8 cycloalkyl, aryl or hetaryl, the radicals R 3 also with formation one of the two oxygen atoms and the boron atom-containing five-membered ring, which can be substituted on the carbon atoms by up to 4 -CC 30 alkyl, C 5 -C 8 cycloalkyl, aryl or hetaryl groups,
  • N, N'-dialkyl-substituted terrylene-3,4: 11,12-tetracarboxylic acid diimides are accessible according to Heterocycles 56, pp. 331-340 (2002) by using an N-alkyl-9-bromoperylene-3,4-dicarboximide 9-tributyltin derivative is reacted, which is then coupled with an N-alkyl-4-halo-naphthalene-1,8-dicarboximide to give the corresponding 9- (4-naphthalene-1,8-dicarboximide) perylene-3,4-dicarboximide, from which the terrylene-3,4: 11,12-tetracarboxylic acid diimide is in turn produced by cyclodehydrogenation.
  • the known production processes have a number of disadvantages: toxic tin compounds and / or strong bases are used in large quantities, the reaction times are very long and / or the overall yield is less than 50%.
  • the object of the invention was therefore to remedy these disadvantages and to provide a process which enables the preparation of terrylene-3,4: 11,12-tetracarbonate diimides in an advantageous, economical manner.
  • X is halogen, C 1 -C 12 -alkylsulfonyl, the alkyl radical of which may be substituted by halogen, or C 6 -C 18 -aryl sulfonyl,
  • alkyl groups occurring in the formulas I to V can be straight-chain or branched. If the alkyl groups are substituted, they usually have 1 or 2 substituents.
  • Cycloalkyl groups and aromatic radicals which are substituted can generally have up to 3, preferably 1 or 2, of the substituents mentioned.
  • Methylthiomethyl 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-butylthioethyl, 2- and 3-methylthiopropyl, 2- and 3-ethylthiopropyl, 2- and 3-propylthiopropyl, 2- and 3- ButylthiopropyI, 2- and 4-methylthiobutyl, 2- and 4-ethylthiobutyl, 2- and 4-propylthiobutyl, 3,6-dithiaheptyl, 3,6-dithiaoctyl, 4,8-dithianonyl, 3,7-dithiaoctyl, 3rd , 7-dithianonyl, 2- and 4-butylthiobutyl, 4,8-dithiadecyl, 3,6,9-trithiadecyl, 3,6,9-trithiaundecy
  • Carbamoyl methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, butylaminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl, octylaminocarbonyl, nonylaminocarbonyl, decylaminocarbonyl and phenylaminocarbonyl;
  • Chlorine, bromine and iodine preferably chlorine or bromine and particularly preferably bromine
  • Methylsulfonyl trifluoromethylsulfonyl, o-, m- and p-tolylsulfonyl;
  • a diborane II with a1) a 9-bromoperylene-3,4-dicarboximide purple or a2) a naphthalene -1, 8-dicarboxylic acid imide Illb (hereinafter 9-bromoperylene-3,4-dicarboxylic acid imide purple and naphthalene-1,8-dicarboximide Illb together briefly called dicarboximide III).
  • the 9- (dioxaborolan-2-yl) perylene-3,4-dicarboximide IVa or 4- (dioxaborolan-2-yl) naphthalene-1, 8-dicarboximide IVb obtained (hereinafter collectively referred to as dioxaborolanyl derivative IV) is obtained in a second step b) subjected to a Suzuki coupling reaction with a naphthalene-1,8-dicarboximide Illb (b1) or a 9-bromoperylene-3,4-dicarboximide purple (b2).
  • step b) The 9- (4-naphthalene-1,8-dicarboximide) perylene-3,4-dicarboximide V obtained in step b) is finally converted into the terrylene-3,4: 11,12 by cyclodeyhydrogenation in a third step c) Tetracarboxylic acid diimide I transferred.
  • Step a) of the production process according to the invention the reaction of the diborane II with the dicarboximide III, is carried out in the presence of an aprotic organic solvent, a transition metal catalyst and a base.
  • the molar ratio of diborane II to dicarboximide III is generally from 0.8 to 3: 1, in particular from 0.9 to 2: 1 and especially from 1 to 1.5: 1.
  • Suitable solvents for step a) are in principle all aprotic solvents which are stable under the reaction conditions to bases and have a boiling point above the chosen reaction temperature, in which the dicarboximides III dissolve completely at the reaction temperature and the catalysts and bases used at least partially dissolve, so that largely homogeneous reaction conditions available. Both non-polar aprotic and polar aprotic solvents can be used, the non-polar aprotic solvents being preferred.
  • nonpolar aprotic solvents are solvents boiling at> 100 ° C. from the following groups: aliphatics (in particular C 8 -C 18 alkanes), unsubstituted, alkyl-substituted and fused cycloaliphatics (in particular unsubstituted C 7 -C 10 cycloalkanes , C 6 -C 8 cycloalkanes which are substituted by one to three CC 6 - alkyl groups, polycyclic saturated hydrocarbons with 10 to 18 C atoms), alkyl and cycloalkyl-substituted aromatics (especially benzene which is substituted by one to three CC 6 - Alkyl groups or a C 5 -C 8 cycloalkyl radical is substituted) and condensed aromatics, which can be alkyl-substituted and / or partially hydrogenated (in particular special naphthalene, which is substituted by one to four C r C 6 alkyl
  • solvents examples include: octane, isooctane, nonane, isononane, decane, isodecane, undecane, dodecane, hexadecane and octadecane; Cycloheptane, cyclooctane, methylcyclohexane, dimethylcyclohexane, trimethylcyclohexane, ethylcyclohexane, diethylcyclohexane, propylcyclohexane, isopropylcyclohexane, dipropylcyclohexane, butylcyclohexane, tert-butylcyclohexane, methylcycloheptane and methylcycloheptane; Toluene, o-, m- and p-xylene, 1, 3,5-trimethylbenzene (mesitylene), 1,2,4- and 1, 2,3-trimethyl
  • Particularly preferred solvents are xylene (all isomers), mesitylene and above all toluene.
  • Suitable polar aprotic solvents are N, N-disubstituted aliphatic carboxamides (in particular NN-di-Crd-alkyl-Crd-carboxamides), nitrogen-containing heterocycles and aprotic ethers (in particular cyclic ethers and di-CrC 6 -alkyl ethers of monomers and oligomeric C 2 -C 3 alkylene glycols, which can contain up to 6 alkylene oxide units, especially diethylene glycol di-CrC 4 alkyl ether).
  • solvents are: N, N-dimethylformamide, N, N-diethylformamide, N, N-dimethylacetamide and N, N-dimethylbutyramide; N-methyl-2-pyrrolidone, quinoline, isoquinoline, quinaldine, pyrimidine, N-methylpiperidine and pyridine; Di- and tetramethyltetrahydrofuran, dioxane, diethylene glycol dimethyl ether and di-ethylene glycol diethyl ether.
  • the amount of solvent is generally 10 to 1000 ml, preferably 15 to 500 ml and particularly preferably 20 to 300 ml per g of dicarboximide III.
  • Palladium complexes such as tetrakis (triphenylphosphine) palladium (0), tetrakis (tris-o-tolylphosphine) palladium (0), [1, 2-bis (diphenylphosphino) ethane] palladium (II) chloride, [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) chloride, bis (triethylphosphine) palladium (II) chloride, bis (tricyclohexylphosphine) palladium (II) acetate, (2,2'-bipyridyl) palladium (II) chloride, bis (triphenylphosphine) palladium (II) chloride, tris (dibenzylidene acetone) dipali metal (0), 1, 5-cycloocadiene palladium (II) chloride, bis (acetonitrile)
  • the transition metal catalyst is usually used in an amount of 1 to 20 mol%, especially 2 to 10 mol%, based on the dicarboximide III.
  • the alkali metal salts in particular the sodium and especially the potassium salts, weak organic and inorganic acids, such as sodium acetate, potassium acetate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate and potassium hydrogen carbonate, are preferably used as the base.
  • Preferred bases are the acetates, especially potassium acetate.
  • 0.1 to 10 mol, preferably 1 to 5 mol and particularly preferably 2 to 4 mol of base are used per mol of dicarboximide III.
  • the reaction temperature is usually 20 to 180 ° C, in particular 40 to 150 ° C and especially 60 to 120 ° C.
  • the reaction time is generally 0.5 to 30 h, preferably 0.5 to 25 h and in particular 1 to 20 h.
  • step a) is expediently carried out as follows:
  • Dicarboximide III and solvent are introduced, diborane II, the transition metal catalyst and the base are added in succession and the mixture is heated under protective gas to the desired reaction temperature for 0.1 to 30 h. After cooling to room temperature, the solid constituents are filtered off from the reaction mixture and the solvent is distilled off under reduced pressure.
  • the purity of the dioxaborolanyl derivative IV thus prepared is generally sufficient for further processing. If appropriate, the crude product can be further purified by washing with a solvent which removes the impurities, such as water, or by column chromatography on silica gel with a mixture of methylene chloride and pentane as the eluent.
  • a solvent which removes the impurities such as water
  • the yield in step a) is usually 75 to 95%.
  • Step b) of the process according to the invention the reaction of the 9- (dioxaborolan-2-yl) perylene-3,4-dicarboximide IVa with the naphthalene-1,8-dicarboximide Illb (b1) substituted in the 4-position by a leaving group or the reaction of 4- (dioxaborolan-2yl) naphthalene-1, 8-dicarboximide IVb with 9-bromperylene-3,4-dicarboximide purple (b2) according to a Suzuki coupling reaction is carried out in presence of an organic solvent, if desired in a mixture with water, and a transition metal catalyst and a base.
  • the molar ratio of 9- (dioxaborolan-2-yl) perylene-3,4-dicarboximide IVa to naphthalene-1,8-dicarboximide Illb is generally 0.8 to 3: 1, preferably 0.9 to 2: 1 and in particular 1 to 1.5: 1.
  • the molar ratio of 4- (dioxaborolan-2yl) naphthalene-1, 8-dicarboximide IVb to 9-bromperylene-3,4-dicarboximide purple is generally 0.3 to 2 : 1, preferably at 0.5 to 1.5: 1 and particularly preferably at 0.7 to 1.3: 1.
  • Suitable solvents for step b) are all solvents in which the dioxa-borolanyl derivatives IV and the 9-bromoperylene-3,4-dicarboximide lilac completely and at least partially dissolve the catalysts and bases used, so that the reaction conditions are largely homogeneous .
  • the solvents already mentioned for step a) are particularly suitable, the alkyl-substituted benzenes also being preferred here.
  • the amount of solvent is usually 10 to 1000 ml, preferably 50 to 500 ml and particularly preferably 75 to 250 ml per g of dioxaborolanyl derivative IV.
  • step b) water is preferably used as an additional solvent.
  • 10 to 1000 ml, in particular 15 to 500 ml and especially 20 to 250 ml of water are generally used per liter of organic solvent.
  • Palladium complexes are also preferably used as transition metal catalysts in step b), the same preferences as in step a) apply here.
  • the amount of catalyst used is usually 1 to 20 mol%, in particular 1.5 to 5 mol%, based on the dioxaborolanyl derivative IV.
  • the alkali metal salts of weak acids are preferred, the carbonates such as sodium carbonate and especially potassium carbonate being particularly preferred.
  • the amount of base is 1 to 100 mol, in particular 5 to 50 mol and especially 10 to 30 mol, per mol of dioxaborolanyl derivative IV.
  • the reaction temperature is generally 20 to 180 ° C, preferably 40 to 150 ° C and particularly preferably 60 to 120 ° C. If water is used in step b), it is advisable not to carry out the reaction at temperatures above 100 ° C., since otherwise pressure would have to be used.
  • the reaction is usually completed in 0.5 to 48 h, in particular in 3 to 24 h and especially in 5 to 20 h.
  • step b) is expediently carried out as follows: 9- (Dioxaborolan-2-yl) perylene-3,4-dicarboximide IVa and naphthalene-1, 8-dicarboximide Illb or 4- (dioxaborolan-2-yl) naphthalen-1, 8-dicarboximide IVb and 9- Bromoperylene-3,4-dicarboximide purple and solvent, add the transition metal catalyst and the base, preferably dissolved in water, and heat the mixture to the desired reaction temperature under protective gas for 0.5 to 48 h. After cooling to room temperature, the organic phase is separated from the reaction mixture and the solvent is distilled off under reduced pressure.
  • the purity of the 9- (4-naphthalene-1,8-dicarboximide) perylene-3,4-dicarboximide V thus prepared is generally sufficient for further processing.
  • the crude product can be further purified by washing with water and, if desired, a suitable organic solvent, in particular a chlorinated aliphatic or aromatic hydrocarbon, or by column chromatography on silica gel using methylene chloride as the eluent.
  • the yield in step b) is usually 90 to 95%.
  • Step c) of the process according to the invention the cyclodehydrogenation of 9- (4-naphthalene-1, 8-dicarboximide) per len-3,4-dicarboximide V to give the terrylene
  • 3,4: 11,12-tetracarboxylic acid diimide I is carried out in an organic reaction medium containing hydroxyl and amino functions and containing an essentially undissolved base.
  • Amino alcohols which have 2 to 20, preferably 2 to 10, carbon atoms are particularly suitable as the organic reaction medium.
  • the carbon chain of these alcohols can be interrupted by ether oxygen atoms.
  • particularly suitable solvents are ethanolamine, triethanolamine and diethanolamine, ethanolamine being preferred. It is also possible to use mixtures of alcohols and amines which each have a boiling point of at least 70 ° C. and are liquid at the reaction temperature.
  • Suitable bases which are essentially insoluble in the reaction medium are the alkali metal salts, in particular the sodium salts and especially the potassium salts, weak organic and preferably weak inorganic acids, such as formates, acetates, propionates, hydrogen carbonates and particularly preferably carbonates, in particular sodium carbonate and above all potassium carbonate.
  • the amount of base is 1 to 3 mol, preferably 1.2 to 2 mol and particularly preferably 1.5 to 1.8 mol per mol of 9- (4-naphthalene-1,8-dicarboximide) perylene-3,4- dicarboximide V.
  • the reaction temperature is generally 40 to 200 ° C, in particular 50 to 180 ° C and especially 80 to 160 ° C.
  • the reaction time is usually 0.5 to 12 h, preferably 0.5 to 6 h and in particular 1 to 4 h.
  • step c) is expediently carried out in such a way that a mixture of 9- (4-naphthalene-1, 8-dicarboximide) perylene-3,4-dicarboximide V, solvent and base is added for 0.1 to 12 h under protective gas the desired reaction temperature, and the terrylene-3,4: 11,12-tetracarboxylic acid diimide I formed, after cooling to room temperature, precipitates out of the reaction mixture by adding an organic solvent, such as ethanol, and is filtered off and washed with water.
  • an organic solvent such as ethanol
  • the terrylene-3,4: 11,12-tetracarboxylic anhydride I isolated in this way is washed with water and, if desired, with an aliphatic alcohol, such as methanol, ethanol, propanol or isopropanol, and then dried in vacuo. If desired, column chromatography on silica gel with a mixture of methylene chloride and acetone as the eluent can also be carried out.
  • the yield in step c) is generally 90 to 100%.
  • the terrylene-3,4: 11,12-tetracarbonate diimides I can be economically viable in good yields (overall yield over all stages generally from 50 to 90%) and high purities (usually 95 to 99%) Way to be made.
  • Terrylene-3,4: 11, 12-tetracarboxylic acid diimides I substituted symmetrically as well as unsymmetrically on the imide nitrogen atoms are advantageously made available.
  • IR (KBr): v 2963, 2929, 2869, 1702, 1665, 1592, 1356, 1142, 1114, 966, 859, 844,
  • UV / VIS (CHCI 3 ): ⁇ max ( ⁇ ) 265 (30569), 485 (36712), 515 nm (36897 M- 1 cm '1 );
  • V 2.1 g of V were obtained in the form of a solid with a melting point of 286 ° C. , which corresponds to a yield of 90%.
  • IR (KBr): v 2958, 2930, 2860, 1701, 1662, 1590, 1576, 1465, 1357, 1235, 1180, 813, 783.754 cm '1 ;
  • UV / VIS (CHCI 3 ): ⁇ max ( ⁇ ) 264 (25703), 336 (12882), 484 (35481), 512 nm (36307
  • CH isopropyl
  • 2.47 (m, 2H, cyclohexyl); 1.85 (m, 2H, cyclohexyl); 1.70 (m, 4H, cyclohexyl); 1.38 (m, 2H, cyclohexyl); 1.14 (d, 12H, CH 3 isopropyl);
  • IR (KBr): v 2961, 2929, 2867, 1995, 1653, 1585, 1379, 1357, 328, 1247, 1183, 1112, 842, 810, 751 cm -1 ;

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Abstract

L'invention concerne un procédé de fabrication de di-imides de l'acide terrylène-3,4:11,12-tétracarboxylique, de formule générale (I) dans laquelle R et R' désignent, indépendamment, l'hydrogène, un C1-C30-alkyle, C5-C8-cycloalkyle, aryle ou hétaryle éventuellement substitué, procédé caractérisé a) en ce qu'on fait réagir un diborane (II) en présence d'un solvant organique aprotique, d'un catalyseur à base d'un métal de transition, et d'une base, avec a1) un imide de l'acide 9-bromo-pérylène-3,4-dicarboxylique (IIIa) ou a2) un imide de l'acide naphtaline-1,8-dicarboxylique (IIIb), b1) en ce que l'imide de l'acide 9-(dioxaborolane-2-yl)pérylène-3,4-dicarboxylique (IVa) formé est soumis, en présence d'un solvant organique de préférence en mélange avec de l'eau, ainsi que d'un catalyseur à base d'un métal de transition et d'une base, à une réaction de couplage Susuki avec un amide de l'acide naphtaline-1,8-dicarboxylique (IIIb) ou b2) l'imide de l'acide 4-(dioxaborolane-2-yl)naphtaline-1,8-dicarboxylique (IVb) formé, est soumis, en présence d'un solvant organique, de préférence en mélange avec de l'eau, ainsi que d'un catalyseur à base d'un métal de transition et d'une base, à une réaction de couplage Susuki, avec un imide de l'acide 9-bromopérylène-3,4-dicarboxylique (IIIa) et, c) l'imide de l'acide 9-(4-naphtaline-1,8-dicarboxylique)pérylène-3,4-dicarboxylique (V) formé est transformé, par cyclodéshydrogénation dans un milieu réactionnel organique présentant des fonctions hydroxy et amino et renfermant une base sensiblement non dissoute, en di-imide de l'acide terrylène-3,4:11,12-tétracarboxylique (I).
PCT/EP2005/000314 2004-01-23 2005-01-14 Procede de fabrication de di-imides de l'acide terrylene-3,4:11,12-tetracarboxylique WO2005070894A1 (fr)

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DE200410003735 DE102004003735A1 (de) 2004-01-23 2004-01-23 Verfahren zur Herstellung von Terrylen-3,4:11,12-tetracarbonsäurediimiden
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US7671202B2 (en) 2004-01-26 2010-03-02 Northwestern University Perylene n-type semiconductors and related devices
US7982039B2 (en) 2004-01-26 2011-07-19 Northwestern University N-type semiconductors and related devices
US7947837B2 (en) 2006-10-25 2011-05-24 Polyera Corporation Organic semiconductor materials and methods of preparing and use thereof
US7902363B2 (en) 2006-11-17 2011-03-08 Polyera Corporation Diimide-based semiconductor materials and methods of preparing and using the same
US7893265B2 (en) 2007-01-08 2011-02-22 Polyera Corporation Methods for preparing arene-BIS (dicarboximide)-based semiconducting materials and related intermediates for preparing same
US8022214B2 (en) 2007-01-24 2011-09-20 Polyera Corporation Organic semiconductor materials and precursors thereof

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