Fluorinated alkyl substituted-thieno[3,4-
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, —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, 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 a polymerizable cyclic pi-conjugated carbon-ring structure optionally comprising S, N or O heteroatoms, and phenyl, naphthyl, pyrryl, dithienyl, thienyl and their respective substituted derivatives.
2. The composition of matter of claim 1 wherein the polymerizable cyclic pi-conjugated carbon-ring structure consists of a pi-conjugated single carbon-ring structure optionally comprising S, N, or O heteroatoms.
3. The composition of matter of claim 1 wherein the polymerizable cyclic pi-conjugated carbon-ring structure consists of a pi-conjugated two or three fused carbon-ring structure optionally comprising S, N or O heteroatoms.
4. The composition of matter of claim 1 wherein at least one of X and X′ is selected from the group consisting of phenyl, naphthyl, pyrryl, dithienyl, thienyl and their respective substituted derivatives.
5. The composition of matter of claim 1 wherein at least one of X and X′ is thieno[3,4-b]thiophene.
6. The composition of matter of claim 1 wherein at least one of X and X′ is thieno[2,3-b]thiophene.
7. The composition of matter of claim 1 which has been treated with a dopant.
8. The composition of matter of claim 1 wherein R is trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluorobutyl, 2,2,2-trifluoromethyl-ethyl and 2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethyl.
9. The composition of matter of claim 1 where in R is perfluorobutyl.
10. The composition of matter of claim 1 further comprising at least one member 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.
11. The composition of matter of claim 1 further comprising ethylenedioxythiophene.
12. The composition of matter of claim 1 further comprising tetrabutylammonium hexafluorophosphate.