Photoactive materials and related compounds, devices, and methods
View Patent ↗The present invention relates to fullerene derivatives including a pendant group that may be reacted to prepare a composition including a plurality of covalently bound fullerenes. The pendant group may be a cyclic ether, such as an epoxide. The present invention also relates to compositions including reaction products of these fullerene derivatives and photovoltaic devices including such polymeric compositions.
1. A fullerene derivative, comprising a pendant cyclic ether and a fullerene comprising a number C j carbon atoms, wherein j ranges from 50 to 250 and the pendant cyclic ether and the fullerene are spaced apart by an ester group or a ketone group.
2. The fullerene derivative of claim 1 , wherein the fullerene is C 60 .
3. The fullerene derivative of claim 1 , wherein the pendant cyclic ether comprises a cyclic group comprising a number Nc carbon atoms and a number No oxygen atoms, in which Nc is at least 2 and No is at least 1.
4. The fullerene derivative of claim 3 , wherein Nc is 4 and No is 1.
5. The fullerene derivative of claim 3 , wherein Nc is 3 and No is 1.
6. The fullerene derivative of claim 3 , wherein No is 1.
7. The fullerene derivative of claim 1 , wherein the pendant cyclic ether is cyclohexene oxide.
8. The fullerene derivative of claim 1 , wherein the pendant cyclic ether is cyclopentene oxide.
9. The fullerene derivative of claim 1 , wherein the pendant cyclic ether is an epoxy group.
10. The fullerene derivative of claim 1 , wherein the pendant cyclic ether and the fullerene are spaced apart by at least 1 carbon atom.
11. The fullerene derivative of claim 1 , wherein the pendant cyclic ether and the fullerene are spaced apart by at least 3 carbon atoms.
12. The fullerene derivative of claim 1 , wherein the pendant cyclic ether and the fullerene are spaced apart by an ester group.
13. A composition, comprising a reaction product of a plurality of fullerene derivatives, each fullerene derivative comprising a pendant cyclic ether and a fullerene comprising a number C j carbon atoms, wherein j ranges from 50 to 250 and the pendant cyclic ether and the fullerene are spaced apart by an ester group or a ketone group.
14. The composition of claim 13 , wherein the fullerene is C 60 .
15. The composition of claim 13 , wherein the reaction product comprises a plurality of ether groups.
16. The composition of claim 13 , wherein the reaction product is an oligomer comprising at least two pendant fullerenes.
17. The composition of claim 13 , wherein the reaction product is a polymer comprising a plurality of repeat units, each repeat unit comprising a pendant fullerene.
18. The composition of claim 13 , wherein the composition further comprises a first conducting polymer.
19. The composition of claim 18 , wherein the first conducting polymer comprises at least one of polyacetylene, polyphenylacetylene, polydiphenylacetylene, polyaniline, poly(p-phenylene vinylene), polythiophene, polyporphyrins, porphyrinic macrocycles, thiol derivatized polyporphyrins, polymetallocenes, polyphthalocyanines, polyvinylenes, or derivatives thereof.
20. The composition of claim 18 , wherein the composition is prepared from a mixture comprising the plurality of fullerene derivatives, and the first conducting polymer or a precursor thereof.
21. The composition of claim 20 , wherein the mixture further comprises a solvent.
22. The composition of claim 20 , wherein the first conducting polymer or precursor thereof comprises a cyclic ether configured to react with the pendant cyclic ether of the fullerene derivatives.
23. The composition of claim 22 , wherein the mixture further comprises a second conducing polymer or a precursor thereof.
24. The composition of claim 23 , wherein the second conducing polymer or precursor thereof comprises a cyclic ether configured to react with the pendant cyclic ether of the first conducting polymer or precursor thereof.
25. The composition of claim 20 , wherein the first conducting polymer or precursor thereof comprises at least one of thiophene, polythiophene, or a derivative thereof.
26. A device, comprising:
a composition comprising a plurality of fullerene derivatives, each fullerene derivative comprising a pendant cyclic ether and a fullerene comprising a number C j carbon atoms, wherein j ranges from 50 to 250; and
an electron donor;
wherein the device is a photovoltaic device comprising two electrodes with the composition and the electron donor between the two electrodes.
27. A device, comprising:
a reaction product of a plurality of fullerene derivatives, each fullerene derivative comprising a pendant cyclic ether and a fullerene comprising a number C j carbon atoms, wherein j ranges from 50 to 250; and
an electron donor;
wherein the device is a photovoltaic device comprising two electrodes with the reaction product and the electron donor between the two electrodes.
28. A composition, comprising:
a reaction product of a plurality of fullerene derivatives, each fullerene derivative comprising a pendant cyclic ether and a fullerene comprising a number C j carbon atoms, wherein j ranges from 50 to 250,
wherein the composition is prepared from a mixture comprising the plurality of fullerene derivatives and a conducting polymer or precursor thereof.
29. A composition, comprising:
a reaction product of a plurality of fullerene derivatives, each fullerene derivative comprising a pendant cyclic ether and a fullerene comprising a number Cj carbon atoms, wherein j ranges from 50 to 250; and
a first conducting polymer.
30. The composition of claim 29 , wherein the first conducting polymer comprises at least one of polyacetylene, polyphenylacetylene, polydiphenylacetylene, polyaniline, poly(p-phenylene vinylene), polythiophene, polyporphyrins, porphyrinic macrocycles, thiol derivatized polyporphyrins, polymetallocenes, polyphthalocyanines, polyvinylenes, or derivatives thereof.
31. The composition of claim 29 , wherein the composition is prepared from a mixture comprising the plurality of fullerene derivatives, and the first conducting polymer or a precursor thereof.
32. The composition of claim 31 , wherein the mixture further comprises a solvent.
33. The composition of claim 31 , wherein the first conducting polymer or precursor thereof comprises a cyclic ether configured to react with the pendant cyclic ether of the fullerene derivatives.
34. The composition of claim 33 , wherein the mixture further comprises a second conducing polymer or a precursor thereof.
35. The composition of claim 34 , wherein the second conducing polymer or precursor thereof comprises a cyclic ether configured to react with the pendant cyclic ether of the first conducting polymer or precursor thereof.
36. The composition of claim 31 , wherein the first conducting polymer or precursor thereof comprises at least one of thiophene, polythiophene, or a derivative thereof.