Perylenetetracarboxylic acid dibenzimidazole sulfoderivatives containing oxo-groups in the perylene core which form part of a para-quinoid system of bonds, lyotropic liquid crystal systems and anisotropic films containing the same, and methods for making the same

A sulfonated perylenetetracarboxylic acid dibenzimidazole (PTCA DBI) compound containing oxo-groups pendant to a perylene core where the oxo-groups and portions of the perylene core form a para-quinoid system of bonds, wherein said compound comprises one of the following structures I to IV:

• where A1 and A2 are, independently, identical or non-identical fragments comprising the following structural formula
• where X1, X3, X4, X5, X6, X7, and X8 are substituents selected, independently, from —H, —OH, and —SO3H,
• where each Y is a substituents selected, independently, from —H, —Cl, —F, —Br, alkyl, —OH, oxyalkyl, —NO2, and NH2,
• where n is an integer selected from 0, 1, and 2, such that at least one of fragments A1 and A2 comprise at least one sulfo group,
• where p is an integer selected from 0, 1, 2, 3 and 4,
• where each M is a counterion and, when n>1, each M can be the same or different, and
• where j is the number of counterions in the molecule and can be fractional if one or more of the counterions belong to several molecules.

A sulfonated perylenetetracarboxylic acid dibenzimidazole (PTCA DBI) compound containing oxo-groups pendant to a perylene core where the oxo-groups and portions of the perylene core form a para-quinoid system of bonds wherein said compound comprises one of the following structures V to VII:

• where A1 and A2 are, independently, identical or non-identical fragments comprising the following structural formula
• where X1, X3, X4, X5, X6, X7, and X8 are substituents selected, independently, from —H, —OH, and —SO3H,
• where Z is divalent bridge chosen from —O—, —SO2—, and —O—SO2—,
• where each Y is a substituent selected, independently, from —H, —Cl, —F, —Br, alkyl, —OH, oxyalkyl, —NO2, and —NH2,
• where n is an integer selected from 0, 1, and 2, such that at least one of fragments A1 and A2 comprises at least one sulfo group,
• where p is an integer selected from 0, 1, 2, 3 and 4,
• where each M is a counterion and, when n>1, each M can be the same or different, and
• where j is the number of counterions in the molecule, which can be fractional if one or more counterions belong to several molecules.

A lyotropic liquid crystal system comprising at least one sulfonated perylenetetracarboxylic acid dibenzimidazole (PTCA DBI) compound containing oxo-groups pendant to a perylene core where the oxo-groups and portions of the perylene core form a para-quinoid system of bonds, wherein said compound comprises one of the following structures I through IV:

• where A1 and A2 are, independently, identical or non-identical fragments comprising the following structural formula
• where X1, X3, X4, X5, X6, X7, and X8 are substituents selected, independently, from —H, —OH, and —SO3H,.
• where each Y is a substituent selected, independently, from —H, —Cl, —F, —Br, alkyl, —OH, oxyalkyl, —NO2, and —NH2,
• where n is an integer selected from 0, 1, and 2, such that at least one of fragments A1 or A2 comprises at least one sulfo group,
• where p is an integer selected from 0, 1, 2, 3 and 4,
• where each M is a counterion and, when n>1, each M can be the same or different, and
• where j is the number of counterions in the molecule, which can be fractional if one or more counterions belong to several molecules.

A lyotropic liquid crystal system comprising at least one sulfonated perylenetetracarboxylic acid dibenzimidazole compound containing oxo-groups pendant to a perylene core where the oxo-groups and portions of the perylene core form a para-quinoid system of bonds, wherein said compound comprises one of the following structures V to VII:

• where A1 and A2 are, independently, identical or non-identical fragments comprising the following structural formula
• where X1, X3, X4, X5, X6, X7, and X8 are substituents selected, independently, from —H, —OH, and —SO3H,
• where Z is a bridge chosen from —O—, —SO2—, and —O—SO2—,
• where each Y is a substituent selected, independently, from —H, —Cl, —F, —Br, alkyl, —OH, oxyalkyl, —NO2, and NH2
• where n is an integer selected from 0, 1, and 2, such that at least one of fragments A1 and A2 comprises at least one sulfo group,
• where p is an integer selected from 0, 1, 2, 3 and 4,
• where each M is a counterion and, when n>1, each M can be the same or different, and
• where j is the number of counterions in the molecule, which can be fractional if one or more counterions belong to several molecules.