Stilbene and fused stilbene derivatives as solar cell dyes
The present application discloses stilbene derivative compounds and phenyl-benzofuran compositions, useful in the manufacture of dye-sensitized solar cells and other similar technology.
1. A solar cell dye for use in a dye sensitized solar cell (DSSC), wherein the dye is a compound of formula I:
wherein either
R 6 is selected from the group consisting of —NR 3 R 4 , —R 3 , —OR 3 and halo; and
R 5 is —(CR═CR—) n (CR═CR 2 —) m R 1 ,
or
R 6 is —(CR═CR—) n (CR═CR 2 —) m R 1 ; and
R 5 is selected from the group consisting of —NR 3 R 4 , —R 3 , —OR 3 and halo,
and
further wherein m is 0 or 1,
and if m is 0, n is an integer from 1-10, and if m is 1, n is an integer from 0-10,
R 1 and R 2 are independently selected from the group consisting of —H, —CN, —COOR, CONHR, CON(H)OR, —SO 3 R, —SO 2 R—OSO 3 R, —PO 3 HR, and —OPO 3 HR, further wherein at least one of R 1 and R 2 is not —H, and if n=m=0 then R 1 is not —H;
each R is independently selected from —H and C 1-6 linear or branched alkyl; and
R 3 and R 4 are independently selected from the group consisting of H, substituted or unsubstituted linear or branched C 1 -C 10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted C 6 -C 10 aryl, substituted or unsubstituted C 5 -C 10 heteroaryl, substituted or unsubstituted C 5 -C 10 cycloalkyl, and substituted or unsubstituted C 5 -C 10 heterocycloalkyl; or R 3 and R 4 attached to their N together form a ring that is substituted or unsubstituted C 5 -C 10 heterocycloalkyl.
2. The dye of claim 1 having the formula II:
3. The dye of claim 1 having the formula III:
4. The dye of claim 1 having the formula IV:
5. The dye of claim 4 wherein R 6 is —NR 3 R 4 .
6. The dye of claim 5 wherein R 6 is selected from the group consisting of diethylamino, diphenylamino, methyl(phenyl)amino, cyclohexyl(methyl)amino, bis(4-methoxyphenyl)amino, bis(4-(tert-butyl)phenyl)amino, di(pyridin-2-yl)amino, di(pyridin-3-yl)amino, di(pyridin-4-yl)amino, piperidin-1-yl, 4-methylpiperazin-1-yl, 4-phenylpiperazin-1-yl, pyrrolidin-1-yl, and morpholino.
7. The dye of claim 4 wherein R 6 is —R 3 or —OR 3 —.
8. The dye of claim 7 wherein R 6 is selected from the group consisting of 3′,4′-dimethoxyphenyl, tert-butyl, phenyoxy, and methoxy.
9. The dye of claim 4 wherein R 6 is halo.
10. The dye of claim 9 wherein R 6 is bromo.
11. The dye of claim 5 wherein R 3 and R 4 are substituted or unsubstituted phenyl.
12. The dye of claim 4 wherein R 1 and R 2 together are —CN and —COOH.
13. A dye sensitized solar cell comprising the solar cell dye of claim 1 .
14. A method of making a DSSC comprising the step of incorporating the solar cell dye of claim 1 into the DSSC.