Compositions and methods for storing holographic data
View Patent ↗In one aspect, the present invention provides a novel thiophene-containing polynitrone compound having structure (II) wherein R 1 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and “a” is an integer from 2 to 4.
1. A thiophene-containing polynitrone compound having structure (II)
wherein R 1 is independently at each occurrence a structure having a formula:
R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and “a” is an integer from 2 to 4.
2. The polynitrone of claim 1 , wherein the nitrone moieties
are attached at positions 2 and 3 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
3. The polynitrone of claim 1 , wherein the nitrone moieties
are attached at positions 2 and 4 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
4. The polynitrone of claim 1 , wherein the nitrone moieties
are attached at positions 2 and 5 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
5. The polynitrone of claim 1 , wherein the nitrone moieties
are attached at positions 3 and 4 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
6. An article comprising the polynitrone of claim 1 .
7. A photo-product of the polynitrone of claim 1 .
8. The photoproduct of claim 7 comprising an oxaziridine having structure (X)
wherein R 1 is independently at each occurrence a structure having a formula:
R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
9. A thiophene-containing dinitrone compound having structure (V)
wherein R 1 is independently at each occurrence a structure having a formula:
R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
10. The dinitrone of claim 9 , wherein the nitrone moieties
are attached at positions 2 and 3 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
11. The dinitrone of claim 9 , wherein the nitrone moieties
are attached at positions 2 and 4 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
12. The dinitrone of claim 9 , wherein the nitrone moieties
are attached at positions 2 and 5 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
13. The dinitrone of claim 9 , wherein the nitrone moieties
are attached at positions 3 and 4 of the thiophene moiety
wherein R 1 is independently at each occurrence a structure having a formula:
R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
14. The composition of claim 9 , where in the dinitrone compound has a structure (VII)
wherein R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
15. The composition of claim 1 , where in the dinitrone compound has a structure (VIII)
wherein R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
16. An article comprising the dinitrone of claim 9 .
17. A photo-product of the dinitrone of claim 9 .
18. The photoproduct of claim 17 comprising structure (XI)
wherein R 1 is independently at each occurrence a structure having a formula:
R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; and R 3 and R 4 are independently halogen, hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical.
19. A method for the preparation of a thiophene-containing polynitrone compound having structure (II),
wherein R 1 is independently at each occurrence a structure having a formula:
R 2 is independently at each occurrence hydrogen, deuterium, a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical, or a C 2 -C 30 aromatic radical; R 5 is independently at each occurrence a C 1 -C 20 aliphatic radical, a C 3 -C 20 cycloaliphatic radical; and “a” is an integer from 2 to 4; said method comprising contacting a carbonyl compound with a hydroxylamine compounds in a solvent at a temperature in a range between about 0° C. and about 50° C.
20. The method according to claim 19 , wherein said solvent comprises acetic acid.