Novel dyes, as well as related photovoltaic cells, components, systems, and methods, are disclosed.
1. A compound, comprising a complex formula (Ia):
MX 3 L (Ia)
wherein
M is a transition metal ion;
each X, independently, is a monodentate ligand selected from the group consisting of thiocyanate, isothiocyanate, and pyridine optionally substituted with halo, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl, or heteroaryl; and
L is a tridentate ligand of formula (II):
in which
R 6 is
in which n is 1, 2, or 3; m is 1, 2, or 3; and each R, independently, is COOH, PO 3 H,
and
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , and R 11 , independently, is H, COOH, PO 3 H, halo, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl, heteroaryl, alkenylaryl, alkynylaryl, alkenylheteroaryl, or alkynylheteroaryl.
2. The compound of claim 1 , wherein R 6 is
3. The compound of claim 1 , wherein the transition metal ion is selected from the group consisting of ruthenium ions, osmium ions, and iron ions.
4. The compound of claim 3 , wherein the transition metal ion is Ru(II), Os(II), or Fe(II).
5. The compound of claim 3 , wherein the transition metal ion is Ru(II).
6. The compound of claim 1 , wherein each X is isothiocyanate.
7. The compound of claim 1 , wherein the complex is
8. The compound of claim 1 , wherein each of R 3 and R 9 , independently, is alkenylaryl, alkynylaryl, heteroaryl, or alkynylheteroaryl.
9. The compound of claim 8 , wherein each of R 3 and R 9 , independently, is
in which n is 1, 2, or 3; m is 1, 2, or 3; and each R, independently, is COOH, PO 3 H,
10. The compound of claim 1 , further comprising a counterion.
11. The compound of claim 10 , wherein the counterion is Bu 4 N + .
12. An article, comprising:
first and second electrodes; and
a photoactive layer between the first and second electrodes, the photoactive layer comprising the compound of claim 1 ;
wherein the article is configured as a photovoltaic cell.
13. The article of claim 12 , wherein the photoactive layer further comprises interconnected metal oxide nanoparticles associated with the compound.
14. A module, comprising a plurality of photovoltaic cells, at least two of the photovoltaic cells being electrically connected and at least one of the photovoltaic cells comprising the compound of claim 1 .
15. A compound, comprising a complex of formula (Ia):
MX 3 L (Ia), and
a counterion Bu 4 N + ,
wherein
M is a transition metal ion;
each X, independently, is a monodentate ligand selected from the group consisting of thiocyanate, isothiocyanate, and pyridine optionally substituted with halo, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl, or heteroaryl; and
L is a tridentate ligand of formula (II):
in which
R 6 is
in which n is 1, 2, or 3; m is 1, 2, or 3; and each R, independently, is COOH, PO 3 H,
and
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , and R 11 , independently, is H, COOH, PO 3 H, halo, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl, heteroaryl, alkenylaryl, alkynylaryl, alkenylheteroaryl, or alkynylheteroaryl.
16. The compound of claim 15 , wherein R 6 is
17. The compound of claim 15 , wherein the transition metal ion is selected from the group consisting of ruthenium ions, osmium ions, and iron ions.
18. The compound of claim 17 , wherein the transition metal ion is Ru(II), Os(II), or Fe(II).
19. The compound of claim 17 , wherein the transition metal ion is Ru(II).
20. The compound of claim 15 , wherein each X is isothiocyanate.
21. The compound of claim 15 , wherein the complex is
22. The compound of claim 15 , wherein each of R 3 and R 9 , independently, is alkenylaryl, alkynylaryl, heteroaryl, alkenylheteroaryl, or alkynylheteroaryl.
23. The compound of claim 22 , wherein each of R 3 and R 9 , independently, is
in which n is 1, 2, or 3; m is 1, 2, or 3; and each R, independently, is COOH, PO 3 H,
24. An article, comprising:
first and second electrodes; and
a photoactive layer between the first and second electrodes, the photoactive layer comprising the compound of claim 15 ;
wherein the article is configured as a photovoltaic cell.
25. The article of claim 24 , wherein the photoactive layer further comprises interconnected metal oxide nanoparticles associated with the compound.
26. A module, comprising a plurality of photovoltaic cells, at least two of the photovoltaic cells being electrically connected and at least one of the photovoltaic cells comprising the compound of claim 15 .
27. A compound, comprising a complex of formula (Ia):
MX 3 L (Ia)
wherein
M is a transition metal ion;
each X, independently, is a monodentate ligand selected from the group consisting of thiocyanate, isothiocyanate, and pyridine optionally substituted with halo, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl, or heteroaryl; and
L is a tridentate ligand of formula (II):
in which
R 3 is H, COOH, PO 3 H, halo, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl, heteroaryl, alkynylaryl, alkenylheteroaryl, or alkynylheteroaryl;
R 6 is
in which n is 1, 2, or 3; m is 1, 2, or 3; and each R, independently, is COOH, PO 3 H,
each of the others of R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , and R 11 , independently, is H, COOH, PO 3 H, halo, C 1 -C 20 alkoxy, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl, heteroaryl, alkenylaryl, alkynylaryl, alkenylheteroaryl, or alkynylheteroaryl.
28. The compound of claim 27 , wherein R 6 is
29. The compound of claim 27 , wherein the transition metal ion is selected from the group consisting of ruthenium ions, osmium ions, and iron ions.
30. The compound of claim 29 , wherein the transition metal ion is Ru(II), Os(II), or Fe(II).
31. The compound of claim 29 , wherein the transition metal ion is Ru(II).
32. The compound of claim 27 , wherein each X is isothiocyanate.
33. The compound of claim 27 , wherein each of R 3 and R 9 , independently, is alkynylaryl, heteroaryl, alkenylheteroaryl, or alkynylheteroaryl.
34. The compound of claim 33 , wherein each of R 3 and R 9 , independently, is
in which n is 1, 2, or 3; m is 1, 2, or 3; and each R, independently, is COOH, PO 3 H
35. The compound of claim 27 , further comprising a counterion.
36. The compound of claim 35 , wherein the counterion is Bu 4 N + .
37. An article, comprising:
first and second electrodes; and
a photoactive layer between the first and second electrodes, the photoactive layer comprising the compound of claim 27 ;
wherein the article is configured as a photovoltaic cell.
38. The article of claim 37 , wherein the photoactive layer further comprises interconnected metal oxide nanoparticles associated with the compound.
39. A module, comprising a plurality of photovoltaic cells, at least two of the photovoltaic cells being electrically connected and at least one of the photovoltaic cells comprising the compound of claim 27 .