Systems for the light-induced separation of charges

1. Perylene bisimide dyads of the general formula (I),

wherein

substituents R 1 to R 11 are identical or different and denote, each independently, hydrogen or a linear alkyl substituent having at least one and at most 37 carbon atoms;

wherein in the alkyl substituent, one to 10 CH 2 units may be replaced, each independently, by a carbonyl group, an oxygen atom, sulfur atom, selenium atom, tellurium atom, a cis or trans CH═CH group in which one CH unit may also be replaced by a nitrogen atom, an acetylenic C≡C group, a divalent phenyl substituent, divalent pyridine substituent, divalent thiophene substituent, divalent naphthalene substituent in which one or two CH groups may be replaced by nitrogen atoms, and a divalent anthracene substituent in which one or two CH groups may be replaced by nitrogen atoms;

wherein up to 12 individual hydrogen atoms of the CH 2 groups may be replaced, in each case each independently even on identical carbon atoms, by the halogens fluorine, chlorine, bromine, or iodine, a cyano group, or a linear alkyl chain having up to 18 carbon atoms in which one to six CH 2 units may be replaced, each independently, by a carbonyl group, an oxygen atom, sulfur atom, selenium atom, tellurium atom, a cis or trans CH═CH group in which one CH unit may be replaced by a nitrogen atom, an acetylenic C≡C group, a divalent phenyl substituent, a divalent pyridine substituent, a divalent thiophene substituent, a divalent naphthalene substituent in which one or two CH groups may be replaced by nitrogen atoms, and a divalent anthracene substituent in which one or two CH groups may be replaced by nitrogen atoms;

wherein up to 12 individual hydrogen atoms of the CH 2 groups in an alkyl substituent may be replaced, in each case each independently even on identical carbon atoms, by the halogens fluorine, chlorine, bromine, or iodine, a cyano group, or a linear alkyl chain having up to 18 carbon atoms in which one to six CH 2 units may be replaced, each independently, by a carbonyl group, an oxygen atom, sulfur atom, selenium atom, tellurium atom, a cis or trans CH═CH group in which one CH unit may be replaced by a nitrogen atom, an acetylenic C≡C group, a divalent phenyl substituent, a divalent pyridine substituent, a divalent thiophene substituent, a divalent naphthalene substituent in which one or two CH groups may be replaced by nitrogen atoms, and a divalent anthracene substituent in which one or two CH groups may be replaced by nitrogen atoms;

wherein CH 2 groups on which a hydrogen atom is replaced as described above may also be linked to one another to form a ring;

wherein substituents R 1 to R 5 and R 7 to R 11 may moreover represent, each independently, the halogen atoms F, Cl, Br or I, or CN;

X in formula (I) signifies one to 12 CH 2 units in which, each independently, one or more may be replaced respectively by a carbonyl group, an oxygen atom, sulfur atom, selenium atom, tellurium atom, a cis or trans CH═CH group in which one CH unit may also be replaced by a nitrogen atom, an acetylenic C≡C group, a divalent phenyl substituent, a divalent pyridine substituent, a divalent thiophene substituent, a divalent naphthalene substituent in which one or two CH groups may be replaced by nitrogen atoms, and a divalent anthracene substituent in which one or two CH groups may be replaced by nitrogen atoms;

wherein up to 12 individual hydrogen atoms of the CH 2 groups'may be replaced, in each case each independently even on identical carbon atoms, by the halogens fluorine, chlorine, bromine, or iodine, a cyano group, or a linear alkyl chain having up to 18 carbon atoms in which one to six CH 2 units may be replaced, each independently, by a carbonyl group, an oxygen atom, sulfur atom, selenium atom, tellurium atom, a cis or trans CH═CH group in which one CH unit may be replaced by a nitrogen atom, an acetylenic C≡C group, a divalent phenyl substituent, divalent pyridine substituent, divalent thiophene substituent, divalent naphthalene substituent in which one or two CH groups may be replaced by nitrogen atoms, and a divalent anthracene substituent in which one or two CH groups may be replaced by nitrogen atoms;

wherein up to 12 individual hydrogen atoms of the CH 2 groups of the alkyl substituents may be replaced, in each case each independently even on identical carbon atoms, by the halogens fluorine, chlorine, bromine, or iodine, a cyano group, or a linear alkyl chain having up to 18 carbon atoms in which one to six CH 2 units may be replaced, each independently, by a carbonyl group, an oxygen atom, sulfur atom, selenium atom, tellurium atom, a cis or trans CH═CH group in which one CH unit may be replaced by a nitrogen atom, an acetylenic C≡C group, a divalent phenyl substituent, divalent pyridine substituent, divalent thiophene substituent, divalent naphthalene substituent in which one or two CH groups may be replaced by nitrogen atoms, and a divalent anthracene substituent in which one or two CH groups may be replaced by nitrogen atoms; and

wherein CH 2 groups on which a hydrogen atom is replaced as described above may also be linked to one another to form a ring.

2. The compound according to claim 1 , wherein substituents R 1 to R 5 are selected from hydrogen and a hydrocarbon substituent.

3. The compound according to claim 1 , wherein R 6 is selected from an aryl substituent or heteroaryl substituent.

4. The compound according to claim 1 , wherein X is a group that is constituted from one or two phenylene groups or one bisphenylene group in combination with one to four methylene units.

5. A method for manufacturing a perylene bisimide dyad , wherein an olefin is reacted by 1,3-dipolar cycloaddition with a nitrone, wherein the perylene bisimide is a perylene bisimide of formula (I) according to claim 1 and the nitrone is a nitrone of formula (II),

wherein R 1 to R 6 and X have the same meaning as in formula (I).

6. A photovoltaic cell comprising a compound according to claim 1 .

7. The photovoltaic cell according to claim 6 , wherein the photovoltaic cell is a titanium oxide cell.

8. A method for converting solar energy into electrical energy comprising using a system for light-driven charge separation comprising a compound according to claim 1 in the presence of solar energy.

9. A method for carrying out a chemical reaction comprising using a compound according to claim 1 as a light-driven reducing or oxidizing agent in a chemical reaction in the presence of light.

10. A method for detecting protonic acids and Lewis acids comprising using a compound according to claim 1 as a fluorescent indicator.