Azide substituted naphthylene or rylene imide derivatives and their use as reagents in click-reactions

A substituted naphthylene or rylene imide derivative of the general formula I

• in which the variables are each defined as follows:
• Y one of the two radicals is a radical of the formula (y2)
• -L-Z—R1 (y2)
• and the other radical in each case is hydrogen;
• R are identical or different radicals:
• aryloxy, arylthio, hetaryloxy or hetarylthio, to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the (i), (ii), (iii), (iv) and/or (v) radicals:
• (i) C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by:
• C1-C12-alkoxy, C1-C6-alkylthio, —C□CR2, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52, —POR5R5, (het)aryl and/or saturated or
• unsaturated C4-C7-cycloalkyl whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the (het)aryl and cycloalkyl radicals may each be mono- or polysubstituted by C1-C18-alkyl and/or the above radicals specified as substituents for alkyl;
• (ii) C3-C8-cycloalkyl whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or
• polysubstituted by:
• C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52 and/or —POR5R5;
• (iii) aryl or hetaryl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by:
• C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52, —POR5R5, (het)aryl, (het)aryloxy and/or (het)arylthio, where the (het)aryl radicals may each be mono- or polysubstituted by C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52, —POR5R5;
• (iv) a —U-aryl radical which may be mono- or polysubstituted by the above radicals specified as substituents for the aryl radicals (iii), where U is a —O—, —S—, —NR3—, —CO—, —SO— or —SO2— moiety;
• (v) C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52 and/or —POR5R5;
• (vi) E-D-SO3−, D is selected from the group of residues as depicted under (ii) and (iii), whereby the counterion of the anion (—SO3−) respectively cation is selected from the group consisting of metal ion and quarternary ammonium ions
• L is a chemical bond or
• an arylene or hetarylene radical, bonded to the rylene skeleton directly or via ethenylene or ethynylene, of the formulae
• —Ar—
• —Ar-E-Ar—
• in which the (het)arylene radicals Ar may be the same or different, may comprise heteroatoms as ring atoms and/or may have fused saturated or unsaturated 5- to 7-membered rings which may likewise comprise heteroatoms, where the entire ring system may be mono- or polysubstituted by phenyl, C1-C12-alkyl, C1-C12-alkoxy, C1-C12-alkylthio and/or —NR3R4;
• E is a chemical bond or an —O—, —S—, —NR2—, —C≡C—, —CR2═CR2— or C1-C6-alkylene moiety;
• Z is —O— or —S— or a carbon-carbon single, double or triple bond, provided that L and Z are not simultaneously a chemical bond;
• R1 is one of the alkyl radicals (i) or (het)aryl radicals (iii) specified as substituents for the R radicals;
• A is:
• hydrogen;
• C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —C≡C—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by the (ii), (iii), (iv) and/or (v) radicals specified as substituents for the R radicals;
• C3-C8-cycloalkyl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the (i), (ii), (iii), (iv) and/or (v) radicals specified as substituents for the R radicals;
• aryl or hetaryl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the (i), (ii), (iii), (iv), (v) radicals specified as substituents for the R radicals, and/or aryl- and/or hetarylazo, each of which may be substituted by C1-C10-alkyl, C1-C6-alkoxy and/or cyano;
• E-D-SO3−, D is selected from the group of residues as depicted under (ii) and (iii), whereby the counterion of the anion (—SO3−) respectively cation is selected from the group consisting of metal ion and quarternary ammonium ions,
• R2 is hydrogen or C1-C18-alkyl, where the R2 radicals may be the same or different when they occur more than once;
• R3, R4 are each independently:
• hydrogen;
• C1-C18-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —CO—, —SO—and/or —SO2— moieties and which may be mono- or polysubstituted by C1-C12-alkoxy, C1-C6-alkylthio, hydroxyl, mercapto, halogen, cyano, nitro and/or —COOR6;
• aryl or hetaryl to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —CO—and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by C1-C12-alkyl and/or the above radicals specified as substituents for alkyl;
• where the R3 radicals may be the same or different when they occur more than once;
• R5 is hydrogen, a C1-C18-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by C1-C12-alkoxy, C1-C6-alkylthio, hydroxyl, mercapto, halogen, cyano, nitro and/or —COOR6;
• aryl or hetaryl to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —CO—and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by C1-C12-alkyl and/or the above radicals specified as substituents for alkyl, where the R5 radicals may be the same or different when they occur more than once;
• R6 is C1-C18-alkyl;
• R7, R8 are each C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —C≡C—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by:
• C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, —NR3R4, —NR3COR4, (het)aryl and/or saturated or unsaturated C4-C7-cycloalkyl whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2— and/or —CR2═CR2 moieties, where the (het)aryl and cycloalkyl
• radicals may each be mono- or polysubstituted by C1-C18-alkyl and/or the above radicals specified as substituents for alkyl;
• aryl or hetaryl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by:
• C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, —NR3R4, —NR3COR4, (het)aryl, (het)aryloxy and/or (het)arylthio, where the (het)aryl radicals may in each case be mono- or
• polysubstituted by C1-C18-alkyl, C1-C12-alkoxy, hydroxyl, —NR3R4 and/or —NR3COR4;
• joined to the nitrogen atom to form a saturated or unsaturated, 5- to 7-membered ring whose carbon chain may be interrupted by one or more —O—, —S— and/or —NR2— moieties, to which may be fused one or two unsaturated or saturated 4- to 8-membered rings whose carbon chain may likewise be interrupted by these moieties and/or —N═, where the entire ring system may be mono- or polysubstituted by C1-C24-alkyl which may be substituted by C1-C18-alkoxy, C1-C18-alkylthio and/or —NR3R4, (het)aryl which may be mono- or polysubstituted by C1-C18-alkyl and/or the above radicals specified as substituents for alkyl, C1-C18-alkoxy, C1-C18-alkylthio and/or —NR3R4;
• m is 0;
• n is an integer in the range of from 0 to 6;
• and
• p is 1.