Photochromic polymers and methods of synthesizing same
Ring-opening metathesis polymerization (ROMP) of a photochromic 1,2-bis-(3-thienyl)-cyclopentene monomer generated a series of novel polymers. All polymers exhibit reversible light-activated interconversion between their colorless-open and their colored-closed forms.
1. A homopolymer of the Formula I:
wherein:
n is any positive integer;
X is CH 2 , CHR 10 , O, S, NH, N-alkyl, N-aryl, or CH 2 —CH 2 ;
R 1 is selected from the group consisting of H, a halogen, a carboxylic acid, an ester, an aldehyde, an alkene, a phenyl, an aryl and structure A, where structure A is:
R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are each selected from the group consisting of H and a halogen;
R 8a , R 8b , R 8c and R 8d are each selected from the group consisting of H, an alkyl and a halogen;
R 9 is a phenyl or an aryl; and,
R 10 is an alkyl, an aryl or a phenyl.
2. A homopolymer according to claim 1 , wherein R 1 is chlorine, phenyl or structure A.
3. A homopolymer according to claim 1 , wherein R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are H or fluorine.
4. A homopolymer according to claim 1 , wherein X is CH 2 or O.
5. A homopolymer according to claim 1 , wherein R 1 is structure A and the homopolymer is cross-linked.
6. A homopolymer according to claim 1 , wherein n is from 10 to 100.
7. A homopolymer according to claim 1 , wherein n is 25.
8. A homopolymer according to claim 1 , wherein n is 50.
9. A homopolymer according to claim 1 , wherein n is 100.
10. A method of preparing a homopolymer according to claim 1 comprising carrying out the reaction steps set forth in any one of the following synthetic schemes A, B, C and D;
11. A method of preparing a photochromic homopolymer using ring-opening metathesis polymerization of a photochromic monomer containing a photochromic dithienylethene pendant group.
12. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 1 .
13. The method as defined in claim 12 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
14. A polymer comprising a compound of Formula VI:
wherein:
X is CH 2 , CHR 10 , O, S, NH, N-alkyl, N-aryl, or CH 2 —CH 2 ;
R 1 is selected from the group consisting of H, a halogen, a carboxylic acid, an ester, an aldehyde, an alkene, a phenyl, an aryl and structure A, where structure A is:
R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are each selected from the group consisting of H and a halogen;
R 8a , R 8b , R 8c , and R 8d are each selected from the group consisting of H, an alkyl and a halogen;
R 9 is a phenyl or an aryl; and,
R 10 is an alkyl, an aryl or a phenyl.
15. A method for polymerization of photochromic dithienyl-alkene monomers to yield photochromic homopolymers comprising performing said polymerization in the presence of Grubbs' catalyst.
16. The method of claim 15 , wherein said photochromic monomer is 1,2-bis-(3-thienyl)-cyclopentene.
17. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 2 .
18. The method as defined in claim 17 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
19. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 3 .
20. The method as defined in claim 19 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
21. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 4 .
22. The method as defined in claim 21 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
23. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 5 .
24. The method as defined in claim 23 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
25. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 6 .
26. The method as defined in claim 25 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
27. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 7 .
28. The method as defined in claim 27 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
29. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 8 .
30. The method as defined in claim 29 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
31. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 9 .
32. The method as defined in claim 31 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
33. A homopolymer according to claim 2 , wherein n is from 10 to 100.
34. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 33 .
35. The method as defined in claim 34 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
36. A homopolymer according to claim 2 , wherein n is 25.
37. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 36 .
38. The method as defined in claim 37 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—these that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
39. A homopolymer according to claim 1 , wherein n is 50.
40. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 39 .
41. The method as defined in claim 40 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.
42. A homopolymer according to claim 1 , wherein n is 100.
43. A method of fabricating a manufacture comprising incorporating in said manufacture a homopolymer according to claim 42 .
44. The method as defined in claim 43 , wherein said manufacture is selected from the group consisting of:
(1) opthalmic lenses-eyeglasses that change color depending on the ambient light;
(2) actinometric devices and molecular sensors;
(3) novelty items such as photochromic inks, paints and fibers;
(4) variable transmission filters—those that on command, regulate the amount and type of light that can be transmitted;
(5) high-density optical information storage systems (this invention is particularly well-suited to this application as it provides more information storage sites per unit area),
(6) photo-regulated molecular switches that can be incorporated into molecular-scale machinery;
(7) optoelectronic systems; and
(8) reversible holographic systems.