Devices containing chiroptical switching materials and methods of making and using the same

Abstract

A polycarbodiimide polymer that is reversibly switchable between two distinct optical orientations is described. The polymer is useful in forming devices such as filters, storage media, actuators, and displays. Methods of making and using such polymers are also described.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic diagram of a first apparatus of the present invention.

FIG. 2 is a schematic diagram of a second apparatus of the present invention.

FIG. 3 is a schematic diagram of a third apparatus of the present invention.

FIG. 4 is a schematic diagram of a fourth apparatus of the present invention.

FIG. 5. Variable-temperature ¹H NMR spectra of R-3 in CD₂Cl₂.

FIG. 6. Stereoregular structures of non-symmetrically substituted polyguanidines prepared through the polymerization of an achiral carbodiimide with catalyst R-1.

FIG. 7. GPC chromatograms of poly-1a and poly-1b eluting with chloroform at a rate of 1.0 mL/min.

FIG. 8. Optical rotations, [α]_D, of poly-1a and poly-1b versus annealing time in toluene at 80° C. (c=0.1 g/100 mL).

FIG. 9. Variable-temperature [α]_D of poly-1b in toluene (c=0.1 g/100 mL) at a heating rate of 1.5° C./min.

FIG. 10. Variable-temperature CD (top) and UV-visible (bottom) spectra of poly-1b in toluene (c=2.1×10⁻⁴ M, path length=10 mm).

FIG. 11. Variable-temperature CD (top) and UV-visible (bottom) spectra of poly-1b in toluene (c=2.1×10⁻⁴ M, path length=10 mm) in the heating-cooling-heating thermal cycle. The sample is the same as that in FIG. 7. The measurement was performed six month later compared to that in FIG. 7.

FIG. 12. Variable-temperature g_abs (top) and UV-visible (bottom) spectra of poly-1b in chloroform (c=2.1×10-4 M, path length=10 mm).

FIG. 13. Variable-temperature g_abs spectra of poly-1b in THF (c=2.1×10⁻⁴ M, path length=10 mm).

FIG. 14. g_abs-values at 380 nm of poly-1b in toluene/THF at 25° C.

FIG. 15. A possible mechanism of the present invention.

Claims

1. A device, comprising: (a) a substrate; and(b) a polycarbodiimide polymer on said substrate,wherein said polycarbodiimide polymer is reversibly switchable between two distinct optical orientations.

2. The device of claim 1, further comprising at least one electrode operatively associated with said polycarbodiimide polymer, and wherein said polycarbodiimide polymer is reversibly switchable between said two distinct optical orientations in response to a change in electric field.

3. The device of claim 2, wherein said electrode is patterned on said substrate.

4. The device of claim 1, wherein said polycarbodiimide polymer is patterned on said substrate.

5. The device of claim 1, wherein said substrate comprises a semiconductor.

6. The device of claim 1, wherein said substrate is optically transparent.

7. The device of claim 1, further comprising an actuator connected to said polycarbodiimide polymer.

8. The device of claim 1, wherein said polycarbodiimide polymer is formed from the polymerization of achiral monomers with an optically active organometallic catalyst.

9. The device of claim 1, wherein said polycarbodiimide polymer comprises repeating units each containing a polycyclic ring.

10. The device of claim 9, wherein said polycyclic ring is substituted with at least one polar or ionic group.

11. A method of switching the optical orientation of a polymer from a first optical orientation to a second optical orientation, comprising: (a) providing a polycarbodiimide polymer in a first optical orientation; and then(b) passing an electric field through said polycarbodiimide polymer to switch said polycarbodiimide polymer from said first optical orientation to said second optical orientation.

12. The method of claim 11, wherein said polycarbodiimide polymer is formed from the polymerization of achiral monomers with an optically active organometallic catalyst.

13. The method of claim 11, wherein said polycarbodiimide polymer comprises repeating units each containing a polycyclic ring.

14. The method of claim 11, wherein said polycarbodiimide polymer switches from said first optical orientation to said second optical orientation within one second at room temperature.

15. The method of claim 11, wherein said polycyclic ring is substituted with at least one polar or ionic group.

16. A compound of Formula I:

17. The compound of claim 16 having the formula:

18. A catalyst composition comprising a compound of claim 16 solubilized in an organic solvent.

19. The catalyst composition of claim 18, wherein said compound is solubilized in said solvent in monomeric form.

20. A method of making a polycarbodiimide polymer of formula II:

21. The method of claim 20, wherein said catalyst is a titanium alkoxide catalyst.

22. The method of claim 20, wherein said polycyclic group is substituted with at least one polar or ionic group.

23. The method of claim 20, wherein said polycyclic group contains at least three fused rings.

24. The method of claim 20, wherein said polycyclic group is selected from the group consisting of anthracene, acridene, chrysene, fluoranthene, perylene, pentacene, dibenzopyrene, dibenzofluoranthene, benzoperylene, dibenzoperylene, rubicene, and decacyclene.

25. A polycarbodiimide polymer of formula II:

26. The polymer of claim 25, wherein said polycyclic group is substituted with at least one polar or ionic group.

27. The polymer of claim 25, wherein said polycyclic group contains at least three fused rings.

28. The polymer of claim 25, wherein said polycyclic group is selected from the group consisting of anthracene, acridene, chrysene, fluoranthene, perylene, pentacene, dibenzopyrene, dibenzofluoranthene, benzoperylene, dibenzoperylene, rubicene, and decacyclene.