Design and synthesis of advanced NLO materials for...

Details Design and synthesis of advanced NLO materials for... Design and synthesis of advanced NLO materials for...

2001-08-17

2004-04-06

Lambkin, Deborah C. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S063000, C549S065000, C549S059000, C549S060000

Reexamination Certificate

active

06716995

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Technical Field
The field of invention is design, synthesis, use, and devices based on advanced nonlinear optical (NLO) materials.
2. Description of the Related Art
All patents, patent applications, and publications cited within this application are incorporated herein by reference to the same extent as if each individual patent, patent application or publication was specifically and individually incorporated by reference.
The development of chromophores demonstrating nonlinear optical (NLO) properties and the uses thereof, including waveguides incorporating the chromophores and the preparation thereof, and the development of organic polymeric matrices to contain the chromophores, and optical devices incorporating the chromophores/waveguides as well as methods of preparing same, are active areas of research. Disclosures related to these areas have appeared in numerous Patents including the following recently issued U.S. Pat. Nos. 5,272,218; 5,276,745; 5,286,872; 5,288,816; 5,290,485; 5,290,630; 5,290,824; 5,291,574; 5,298,588; 5,310,918; 5,312,565; 5,322,986; 5,326,661; 5,334,333; 5,338,481; 5,352,566; 5,354,511; 5,359,072; 5,360,582; 5,371,173; 5,371,817; 5,374,734; 5,381,507; 5,383,050; 5,384,378; 5,384,883; 5,387,629; 5,395,556; 5,397,508; 5,397,642; 5,399,664; 5,403,936; 5,405,926; 5,406,406; 5,408,009; 5,410,630; 5,414,791; 5,418,871; 5,420,172; 5,443,895; 5,434,699; 5,442,089; 5,443,758; 5,445,854; 5,447,662; 5,460,907; 5,465,310; 5,466,397; 5,467,421; 5,483,005; 5,484,550; 5,484,821; 5,500,156; 5,501,821; 5,507,974; 5,514,799; 5,514,807; 5,517,350; 5,520,968; 5,521,277; 5,526,450; 5,532,320; 5,534,201; 5,534,613; 5,535,048; 5,536,866; 5,547,705; 5,547,763; 5,557,699; 5,561,733; 5,578,251; 5,588,083; 5,594,075; 5,604,038; 5,604,292; 5,605,726; 5,612,387; 5,622,654; 5,633,337; 5,637,717; 5,649,045; 5,663,308; 5,670,090; 5,670,091; 5,670,603; 5,676,884; 5,679,763; 5,688,906; 5,693,744; 5,707,544; 5,714,304; 5,718,845; 5,726,317; 5,729,641; 5,736,592; 5,738,806; 5,741,442; 5,745,613; 5,746,949; 5,759,447; 5,764,820; 5,770,121; 5,76,374; 5,776,375; 5,777,089; 5,783,306; 5,783,649; 5,800,733; 5,804,101; 5,807,974; 5,811,507; 5,830,988; 5,831,259; 5,834,100; 5,834,575; 5,837,783; 5,844,052; 5,847,032; 5,851,424; 5,851,427; 5,856,384; 5,861,976; 5,862,276; 5,872,882; 5,881,083; 5,882,785; 5,883,259; 5,889,131; 5,892,857; 5,901,259; 5,903,330; 5,908,916; 5,930,017; 5,930,412; 5,935,491; 5,937,115; 5,937,341; 5,940,417; 5,943,154; 5,943,464; 5,948,322; 5,948,915; 5,949,943; 5,953,469; 5,959,159; 5,959,756; 5,962,658; 5,963,683; 5,966,233; 5,970,185; 5,970,186; 5,982,958; 5,982,961; 5,985,084; 5,987,202; 5,993,700; 6,001,958; 6,005,058; 6,005,707; 6,013,748; 6,017,470; 6,020,457; 6,022,671; 6,025,453; 6,026,205; 6,033,773; 6,033,774; 6,037,105; 6,041,157; 6,045,888; 6,047,095; 6,048,928; 6,051,722; 6,061,481; 6,061,487; 6,067,186; 6,072,920; 6,081,632; 6,081,634; 6,081,794; 6,086,794; 6,090,322; and 6,091,879. The entire disclosure of these patents is hereby incorporated herein by reference for all purposes.
Despite the attention given to this area, there is a pressing need for improved chromophores that can be used in electro-optic applications and related uses. The present invention is directed to fulfilling this need and providing uses, devices, and communication systems based on non-linear optically active chromophores.
SUMMARY OF THE INVENTION
In various aspects, chromophores comprise of novel electron acceptors (A), novel electron donors (D), and/or novel conjugated bridges (p). The chromophores have non-linear optical properties, i.e., are NLO chromophores.
In one aspect, a thiophene-containing chromophore has the structure
wherein, independently at each occurrence, D is an electron donating group having low electron affinity relative to the electron affinity of A; &pgr;
1
is absent or a bridge that provides electronic conjugation between D and the thiophene ring; &pgr;
2
is absent or a bridge that provides electronic conjugation between A and the thiophene ring; A is an electron accepting group having high electron affinity relative to the electron affinity of D; X is O or S; R is alkyl, aryl, heteroalkyl or heteroaryl; and n is 1, 2, 3 or 4.
Specific D groups that may be incorporated into a chromophore include, without limitation, D groups of the following structures,
wherein, independently at each occurrence, R is alkyl, aryl or heteroalkyl; R
1
is hydrogen, alkyl, aryl or heteroalkyl; Y is O, S or Se; m is 2, 3 or 4; p is 0, 1 or 2; and q is 0 or 1. In one embodiment, R contains 1-12 carbons; R
1
is hydrogen or contains 1-12 carbons; Y is O or S; m is 2, 3 or 4; p is 0, 1 or 2; and q is 0 or 1. Some preferred D groups that may be present in a chromophore according to the present invention are of the structures:
In one aspect of the invention, the chromophore contains both &pgr;
1
and &pgr;
2
groups, i.e., the &pgr;
1
and &pgr;
2
groups are not absent from the chromophore. One or both of &pgr;
1
and &pgr;
2
may be, independently at each occurrence, of the structure
wherein, independently at each occurrence, Z
1
is O, S, Se, NR
1
, C(R
1
)2 or —C(R
1
)═C(R
1
)—; p is 0, 1 or 2; o is 0, 1 or 2; o+p is at least 1; R
1
is hydrogen, alkyl, aryl or heteroalkyl;
Z
2
is
and q is 0 or 1.
Some specific structures for &pgr;
1
and &pgr;
2
are:
wherein, independently at each occurrence, R
1
is hydrogen, alkyl, aryl or heteroalkyl; Z
1
is O, S, Se, NR
1
, C(R
1
)
2
or —C(R
1
)═C(R
1
)—; p is 0, 1 or 2; o is 0, 1 or 2; o+p is at least 1; and q is 0 or 1. In one aspect each of &pgr;
1
and &pgr;
2
are —CH═CH—.
Some specific A groups that may be incorporated into chromophores according to the present invention are:
wherein, independently at each occurrence, R is alkyl, aryl or heteroalkyl; R
1
is hydrogen, alkyl, aryl or heteroalkyl; Y is O, S or Se; and q is 0 or 1. Optionally, R contains 1-12 carbons; R
1
is hydrogen or contains 1-12 carbons; Y is 0 or S; and q is 0 or 1. A specifically preferred A group is of the formula
In various aspects of the invention, R is alkyl, and/or aryl, and/or heteroalkyl, and/or heteroaryl, including each and every combination thereof. Optionally, R is hydrophobic, while alternatively R is hydrophilic. Optionally, an R group is saturated, while alternatively an R group is unsaturated. The R group may have, in various aspects of the invention, 1-6 carbons, or 7-12 carbons, or 13-22 carbons.
The value of n may be 1, or 2, or 3, or 4, or each and every combination thereof, e.g., 2 or 3. In one aspect, X is O, while in another aspect X is S.
In one chromophore according to the present invention, &pgr;
1
and &pgr;
2
are
and A is
wherein R is independently at each occurrence alkyl, aryl or heteroalkyl.
Thus, in one aspect, a thiophene-containing chromophore has of the structure
wherein, independently at each occurrence, D is selected from the group consisting of
&pgr;
1
and &pgr;
2
are independently
A is selected from the group consisting of
X is O or S; R is alkyl, aryl or heteroalkyl; n is 1, 2, 3 or 4; R
1
is hydrogen, alkyl, aryl or heteroalkyl; Y is O, S or Se; Z
1
is O, S, Se, NR
1
, C(R
1
)
2
or —C(R
1
)═C(R
1
)—;
Z
2
is
q is 0 or 1; p is 0, 1 or 2; o is 0, 1 or 2; o+p is at least 1; and m is 2, 3 or 4.
In another chromophore according to the present invention, D is selected from:
and &pgr; is selected from:
In another aspect, a chromophore has the structure
wherein, independently at each occurrence, R is alkyl, aryl or heteroalkyl; R
1
is alkyl, aryl or heteroalkyl; and X is O or S. For example, R may be —(CH
2
)
w
OH, —(CH
2
)
w
OR
1
, —(CH
2
)
w
SH, —(CH
2
)
w
CO
2
Et, —(CH
2
)
w
CO
2
H, —(CH
2
)
w
NH
2
, —(CH
2
)
w
CN, —(CH
2
)
w
halogen, or —COC
6
H
4
OCF═CF
2
where w is an integer selected from 1-12; and R
1
may be hydrogen, R, perfluoroalkyl, SiR
3
, Si(CH
3
)
2
t-Bu, or Si(i-Pr)
3
.
In another aspect, a chromophore has the structure
wherein, independently at each occurrence, R is alkyl, aryl or heteroalkyl; R
1
is alkyl, ary

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