Fluorinated alkyl substituted-thieno[3,4-]thiophene monomers and polymers therefrom
View Patent ↗Partially and fully fluorinated alkyl substituted thienothiophene monomers (and polymers thereof) wherein the monomers are represented by the formula: wherein R is a partially or fully fluorinated primary, secondary or tertiary alkyl having from 1 to 8 carbon atoms; and X and X′ are independently selected from the group consisting of H, F, Cl, Br, I, MgCl, MgBr, Mgl, Sn(R′) 3 , CH═CHR″, —OR″, —COOR″, —S—COR″, —B(OR″) 2 , —COR″, —C≡CH, and a polymerizable cyclic pi-conjugated carbon-ring structure optionally comprising S, N or O heteroatoms; wherein R′ is a primary, secondary or tertiary alkyl having from 1 to 6 carbon atoms, and R″ is H or a primary, secondary or tertiary alkyl having from 1 to 6 carbon atoms.
1. A composition of matter represented by the formula
wherein
R is a partially or fully fluorinated primary, secondary or tertiary alkyl having from 1 to 8 carbon atoms; and
X and X′ are independently selected from the group consisting of H, F, Cl, Br, I, MgCl, MgBr, Mgl, Sn(R′) 3 ,
CH═CHR″, —OR″, —COOR″, —S—COR″, —B(OR″) 2 ,
—COR″, —C≡CH, and a polymerizable cyclic pi-conjugated carbon-ring structure optionally comprising S, N or O heteroatoms;
wherein
R′ is a primary, secondary or tertiary alkyl having from 1 to 6 carbon atoms, and
R″ is H or a primary, secondary or tertiary alkyl having from 1 to 6 carbon atoms.
2. The composition of matter of claim 1 wherein R is a fully fluorinated primary, secondary or tertiary alkyl having from 1 to 8 carbon atoms.
3. The composition of matter of claim 2 wherein X and X′ are H and R is a fully fluorinated primary, secondary or tertiary alkyl having 4 carbon atoms.
4. The composition of matter of claim 2 wherein at least one of X and X′ is represented by the formulae
5. The composition of matter of claim 2 wherein at least one of X and X′ is selected form the group consisting of F, Cl, Br and I.
6. A composition of matter represented by the formula
wherein
R is a fully fluorinated primary, secondary or tertiary alkyl having from 1 to 8 carbon atoms,
n is an integer,
Y is —CZ 1 ═CZ 2 —, —C≡C— phenyl, naphthyl, pyrryl, thienyl, thieno[3,4,b]thiophene, thieno[2,3-b]thiophene and their respective substituted derivatives, and
Z 1 and Z 2 are independently selected from H, F, Cl or CN.
7. The composition of matter of claim 6 wherein n is an integer from 2 to 10, inclusive.
8. The composition of matter of claim 6 wherein n is an integer from 11 to 50,000, inclusive.
9. The composition of matter of claim 8 wherein Y is —CH═CH—.
10. The composition of matter of claim 8 wherein Y is —C≡C—.
11. The composition of matter of claim 8 wherein Y is selected from the group consisting of phenyl, naphthyl, pyrryl, thienyl, thieno[3,4,b]thiophene, thieno[2,3-b]thiophene and their respective substituted derivatives.
12. The composition of matter of claim 11 which has been treated with a dopant.
13. The composition of matter of claim 12 wherein the dopant is a p-type dopant.
14. The composition of matter of claim 12 wherein the dopant is an n-type dopant.
15. The composition of claim 11 dispersed in a fluid.
16. The composition of claim 15 wherein the fluid comprises water.
17. The composition of claim 15 wherein the fluid is water.
18. A composition of matter represented by the formula:
where R is a fully fluorinated primary, secondary or tertiary alkyl having from 1 to 8 carbon atoms and n is an integer from 2 to 50,000, inclusive.
19. The composition of matter of claim 18 wherein R is trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluorobutyl, 2,2,2-trifluoromethyl-ethyl and 2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethyl.
20. The composition of matter of claim 18 where in R is perfluorobutyl.
21. The composition of matter of claim 18 which has been treated with a dopant.
22. The composition of matter of claim 21 wherein the dopant is a p-type dopant.
23. The composition of matter of claim 21 wherein the dopant is an n-type dopant.
24. The composition of matter of claim 22 dispersed in a fluid selected from the consisting of polyacrylic acid, polymethacrylic acid, polymaleic acid, polystyrene sulfonic acid, a perfluorosulfonic acid polymer, polyvinyl sulfonic acid and poly(styrene-co-acrylonitrile) sulfonic acid and mixtures thereof.