Phenyltetraene-based nonlinear optical chromophores
Alkoxy-substituted phenyltetraene nonlinear optically active compounds, films and devices that include the compounds, and methods for making and using the compounds, films, and devices.
1. A compound of the structure
wherein
D is selected from the group consisting of a diarylamino group, a dialkylamino group, and an arylalkylamino group;
A is
wherein R a1 and R a2 are independently selected from the group consisting of alkyl, fluorinated alkyl, perfluorinated alkyl, substituted alkyl, aryl, fluorinated aryl, perfluorinated aryl, substituted aryl, heteroaryl, and substituted heteroaryl, and
X 1 , X 2 , and X 3 are independently selected from the group consisting of fluoro, cyano, trifluoromethyl, and trifluoromethylsulfonyl;
R 1 and R 2 are independently selected from the group consisting of
(a) hydrogen, and
(b) C1-C6 alkyl; or
R 1 and R 2 taken together with the carbon atom to which they are attached form a 3- to 7-membered ring; and
R 3 is selected from the group consisting of substituted and unsubstituted C1-C12 alkyl.
2. The compound of claim 1 , wherein R 3 is C1-C12 unsubstituted alkyl.
3. The compound of claim 1 , wherein R 3 is C1-C12 n-alkyl.
4. The compound of claim 1 , wherein substituted C1-C12 alkyl is a C1-C12 alkyl in which one or more hydrogen atoms is replaced with one or more halogen atoms.
5. The compound of claim 1 , wherein substituted C1-C12 alkyl is C n F 2n+1 , wherein n is an integer from 1 to 12.
6. The compound of claim 1 , wherein substituted C1-C12 alkyl is C n H 2n OR 4 , wherein n is an integer from 1 to 12, and R 4 is selected from the group consisting of hydrogen, alkyl, aryl, and acyl.
7. The compound of claim 1 , wherein R 3 is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, and n-pentyl.
8. The compound of claim 1 , wherein R 1 and R 2 are methyl.
9. The compound of claim 1 , wherein D is dialkylamino.
10. The compound of claim 1 , wherein A is tricyanofuranylidene.
11. A film comprising a compound of claim 1 .
12. The film of claim 11 further comprising a host material.
13. The film of claim 12 , wherein the host material comprises a crosslinked polymer network.
14. The film of claim 11 further comprising a second nonlinear optical chromophore.
15. An electro-optic device, comprising a compound of claim 1 .
16. The compound of claim 1 , wherein the diarylamino group, the dialkylamino group, or the arylalkylamino group is substituted with a crosslinkable group or a dendron.
17. The compound of claim 1 , wherein D is
wherein n and m are independently an integer from 1 to 6, and
A and B are independently selected from the group consisting of hydrogen, methyl or —OR, wherein R is hydrogen, C1-C6 alkyl, aryl, acyl, a crosslinkable group or a dendron optionally substituted with a crosslinkable group.