Perylenemonoimide and naphthalenemonoimide derivatives and their use in dye-sensitized solar cells

A method for making a compound of formula (I′):

• wherein:
• R1, R2 are each independently hydrogen, a halogen, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group;
• m, n are each independently an integer of 0, 1, 2, 3, or 4;
• X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group;
• and
• Y1 is oxygen or N—Z-A, wherein:
• A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]14+, where each R′ is independently hydrogen or an alkyl group;
• and
• Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano and/or halogen substituents,
• the method comprising:
• reacting a compound of formula (II) with a hydroxide alkaline agent or reacting the compound of formula (II) with a hydroxide alkaline agent and then an amine of formula (III):
• wherein:
• R1, R2 are each independently hydrogen, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group;
• m, n are each independently an integer of 0, 1, 2, 3, or 4;
• q is 1;
• X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group, and
• Y2is NR4, where R4 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group or a hetaryl group,
• H2N—Z-A (III)
• wherein:
• A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]4+, where each R′ is independently hydrogen or an alkyl group:
• and
• Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano and/or halogen substituents.

A dye-sensitized solar cell, comprising:

• a compound of formula (I′)
• wherein:
• R1, R2 are each independently hydrogen, a halogen, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group;
• m, n are each independently an integer of 0, 1, 2, 3, or 4;
• X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group;
• and
• Y1 is oxygen or N—Z-A, wherein:
• A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]4+, where each R′ is independently hydrogen or an alkyl group;
• and
• Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano and/or halogen substituents.