Alkylenedioxythiophenes and poly(alkylenedioxythiophenes) containing mesogenic groups

A 3,4-Alkylenedioxythiophene of the formula (I),

• wherein
• A is a C1-C5-alkylene radical which is substituted at any point by a linker L and optionally bears further substituents,
• L is a methylene group,
• p is 0 or an integer from 1 to 6,
• M is an n-functional steroid radical or a derivative of a steroid radical,
• n island
• B′ is a bridging group of the formula (B)
• wherein
• q is 0 or 1,
• r and s are each independently 0 or 1, with the proviso that when r is 1, s is 0 and vice versa or both are optionally 0,
• t is 0 or 1,
• Sp is a spacer selected from the group consisting of substituted and unsubstituted linear or cyclic C1-C20-alkylene groups, C5-C20-arylene groups, C2-C20-heteroarylene groups in which from one to three heteroatoms selected from the group consisting of N, O and S can additionally be present in the heteroaromatic ring or ring system, C6-C20-aralkylene groups, C2-C200-oligoether and -polyether groups,
• m is 0 or 1,
• Q is O, S or NH.

A 3,4-Alkylenedioxythiophene of the formula (I),

• wherein
• A is a C1-C5-alkylene radical which is substituted at any point by a linker L and optionally bears further substituents,
• M is an n-functional group of the formula (II-a), (II-b) or (II-c-1) to (II-c-6),
• wherein
• X3, X2 and X3 are substituted or unsubstituted structures selected independently from the group consisting of
• and
• Z1 and Z2 are structures selected independently from the group consisting of
• wherein
• Rx and Ry are each, independently of one another, H, substituted or unsubstituted C1-C22-alkyl, C1-C22-haloalkyl, C1-C22-alkenyl, C1-C22-alkoxy, C1-C22-thioalkyl, C1-C22-iminoalkyl, C1-C22-alkoxycarbonyl, C1-C22-alkoxycarbonyloxy, a radical of an aliphatic C1-C22-alkanecarboxylic acid or of acrylic acid, halogen, pseudohalogen, NO2, a carboxyl group or a hydroxy group,
• h is an integer from 1 to 10,
• w is an integer from 1 to 5,
• x, y and z are each, independently of one another, 0 or 1, and
• n an integer from 1 to 8, where when n is an integer below 8, the group is selected from the group consisting of formulas (II-c-1), (II-c-2), (II-c-3), (II-c-4), (II-c-5) and (II-c-6) and bears a terminal group F′ on the remaining 8-n linkage points denoted by * when n is 1, the group of the formula (II-a) or (II-b) and bears a terminal group F′ at the linkage points denoted by *,
• wherein
• F′ is substituted or unsubstituted C1-C22-alkyl, C1-C22-haloalkyl, C1-C22-alkenyl, C1-C22-alkoxy, C1-C22-thioalkyl, C1-C22-iminoalkyl, C1-C22-alkoxycarbonyl, C1-C22-alkoxycarbonyloxy, a radical of an aliphatic C1-C22-alkanecarboxylic acid or of acrylic acid, halogen, pseudohalogen, a nitro (NO2) group, a carboxyl group, a sulphonic acid group or sulphonate group or a hydroxy group,
• B′ is a bridging group of the formula (B)
• wherein
• q is 0 or 1,
• r and s are identical or different and each are 0 or 1, with the proviso that when r is 1, s is 0 and vice versa or both are optionally 0,
• t is 0 or 1,
• Sp is a spacer selected from the group consisting of substituted and unsubstituted linear or cyclic C1-C20-alkylene groups, C5-C20-arylene groups, C2-C20-heteroarylene groups in which from one to three heteroatoms selected from the group consisting of N, O and S can additionally be present in the heteroaromatic ring or ring system, C6-C20-aralkylene groups, C2-C200-oligoether and polyether groups,
• m is 0 or 1, and
• Q is QS or NH.

A 3,4-Alkylenedioxythiophene of the formula (I),

• wherein
• A is a C1-C5-alkylene radical which is substituted at any point by a linker L and optionally bears further substituents,
• M is an n-functional group of the formula (II-a), (II-b) or (II-c-1) to (II-c-6),
• wherein
• X1, X2 and X3 are substituted or unsubstituted structures selected independently from the group consisting of
• and
• Z1 and Z2 are structures selected independently from the group consisting of
• wherein
• Rx and Ry are each, independently of one another, H, substituted or unsubstituted C1-C22-alkyl, C1-C22-haloalkyl, C3-C22-alkenyl, C1-C22-alkoxy, C1-C22-thioalkyl, C1-C22-iminoalkyl, C1-C22-alkoxycarbonyl, C1-C22-alkoxycarbonyloxy, a radical of an aliphatic C1-C22-alkanecarboxylic acid or of acrylic acid, halogen, pseudohalogen, NO2, a carboxyl group or a hydroxy group,
• h is an integer from 1 to 10,
• w is an integer from 1 to 5,
• x, y and z are each, independently of one another, 0 or 1, and
• n an integer from 1 to 8, where when n is an integer below 8, the group is selected from the group consisting of formulas (II-c-1), (II-c-2), (II-c-3), (II-c-4), (II-c-5) and (II-c-6) and bears a terminal group F′ on the remaining 8-n linkage points denoted by * when n is 1, the group of the formula (II-a) or (II-b) and bears a terminal group F′ at the linkage points denoted by *,
• wherein
• F′ is H, substituted or unsubstituted C1-C22-alkyl, C1-C22-haloalkyl, C1-C22-alkenyl, C1-C22-alkoxy, C1-C22-thioalkyl, C1-C22-iminoalkyl, C1-C22-alkoxycarbonyl, C1-C22-alkoxycarbonyloxy, a radical of an aliphatic C1-C22-alkanecarboxylic acid or of acrylic acid, halogen, pseudohalogen, a nitro (NO2) group, a carboxyl group, a sulphonic acid group or sulphonic group or a hydroxy groups
• B′ is a bridging group of the formula (B)
• wherein
• q is 0 or 1,
• r is 1,
• s is 0,
• t is 0 or 1,
• Sp is a spacer selected from the group consisting of substituted and unsubstituted linear or cyclic C1-C20-alkylene groups, C5-C20-arylene groups, C2-C20-heteroarylene groups in which from one to three heteroatoms selected from the group consisting of N, O and S can additionally be present in the heteroaromatic ring or ring system, C6-C20-aralkylene groups, C2-C200-oligoether and polyether groups,
• m is 0 or 1, and
• Q is O, S or NH.

A polythiophene which comprise recurring units of the formula (IV),

• wherein
• A is a C1 or C3-C5-alkylene radical which is substituted at any point by a linker L and optionally bears further substituents,
• L is a methylene group,
• p is an integer from 1 to 6,
• M is an n-functional group of the formula (II-a), (II-b) or (II-c-1) to (II-c-6),
• wherein
• X1, X2 and X3 are substituted or unsubstituted structures selected independently from the group consisting of
• and
• Z1 and Z2 are structures selected independently from the group consisting of
• wherein
• Rx and Ry are each, independently of one another, H, substituted or unsubstituted C1-C22-alkyl, C1-C22-haloalkyl, C1-C22-alkenyl, C1-C22-alkoxy, C1-C22-thioalkyl, C1-C22-iminoalkyl, C1-C22-alkoxycarbonyl, C1-C22-alkoxycarbonyloxy, a radical of an aliphatic C1-C22-alkanecarboxylic acid or of acrylic acid, halogen, pseudohalogen, NO2, a carboxyl group or a hydroxy group,
• h is an integer from 1 to 10,
• w is an integer from 1 to 5,
• x, y and z are each, independently of one another, 0 or 1, and
• n an integer from 1 to 8, where when n is an integer below 8, the group is selected from the group consisting of formulas (II-c-1), (II-c-2), (II-c-3), (II-c-4), (II-c-5) and (II-c-6) and bears a terminal group F′ on the remaining 8-n linkage points denoted by * when n is 1, the group of the formula (II-a) or (II-b) and bears a terminal group F′ at the linkage points denoted by *,
• wherein
• F′ is H, substituted or unsubstituted C1-C22-alkyl, C1-C22-haloalkyl, C1-C22-alkenyl, C1-C22-alkoxy, C1-C22-thioalkyl, C1-C22-iminoalkyl, C1-C22-alkoxycarbonyl, C1-C22-alkoxycarbonyloxy, a radical of an aliphatic C1-C22-alkanecarboxylic acid or of acrylic acid, halogen, pseudohalogen, a nitro (NO2) group, a carboxyl group, a sulphonic acid group or sulphonic group or a hydroxy group,
• B′ is a bridging group of the formula (B)
• wherein
• q is 0 or 1,
• r and s are identical or different and each are 0 or 1, with the proviso that when r is 1, s is 0 and vice versa or both are optionally 0,
• t is 0 or 1,
• Sp is a spacer selected from the group consisting of substituted and unsubstituted linear or cyclic C1-C20-alkylene groups, C5-C20-arylene groups, C2-C20-heteroarylene groups in which from one to three heteroatoms selected from the group consisting of N, O and S can additionally be present in the heteroaromatic ring or ring system, C6-C20-aralkylene groups, C2-C200-oligoether and polyether groups,
• m is 0 or 1, and
• Q is O, S or NH.