Fluoranthene copolymers and methods of making and using the same
View Patent ↗The present application relates to copolymers having at least one optionally substituted fluoranthene as a first monomer unit and at least one optionally substituted pyrrole as a second monomer unit. The copolymer may, for example, emit green light when exposed to a blue or ultraviolet radiation. Methods of making the copolymer are also disclosed, as well as methods and apparatuses for producing light and detecting nitroaromatics using the copolymer.
1. A copolymer comprising at least one optionally substituted fluoranthene as a first monomer unit and at least one optionally substituted pyrrole as a second monomer unit.
2. The copolymer of claim 1 , where the first monomer unit is represented by Formula I:
wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 hydroxyalkyl, ester, carboxy, and C 1-6 alkyl-N(R 5 )(R 6 ), and
wherein R 5 and R 6 are each independently selected from hydrogen and C 1-6 alkyl.
3. The copolymer of claim 2 , wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen and C 1-6 alkyl.
4. The copolymer of claim 2 , wherein R 1 , R 2 , R 3 , and R 4 are each hydrogen.
5. The copolymer of claim 2 , wherein R 1 and R 2 are the same.
6. The copolymer of claim 2 , wherein R 3 and R 4 are the same.
7. The copolymer of claims 1 , wherein the second monomer unit is represented by Formula II:
wherein R 7 , R 8 , and R 9 are each independently selected from the group consisting of hydrogen and C 1-6 alkyl.
8. The copolymer of claim 7 , wherein R 7 , R 8 , and R 9 are each hydrogen.
9. The copolymer of claim 7 , wherein R 8 and R 9 are the same.
10. The copolymer of claim 1 , wherein the copolymer comprises at least about 30% of the first monomer unit by mole.
11. The copolymer of claim 1 , wherein the copolymer comprises no more than about 99% of the first monomer unit by mole.
12. The copolymer of claim 1 , wherein the copolymer comprises at least about 1% of the second monomer unit by mole.
13. The copolymer of claim 1 , wherein the copolymer comprises no more than about 70% of the second monomer unit by mole.
14. The copolymer of claim 1 , wherein the molar ratio of the first monomer unit to the second monomer unit is about 30:70 to about 99:1.
15. The copolymer of claim 1 , wherein the copolymer exhibits an electrical conductivity of at least 10 −6 S·cm −1 when doped with an effective amount of a dopant.
16. The copolymer of claim 15 , wherein the dopant is iodine.
17. The copolymer of claim 1 , wherein the copolymer exhibits a green emission when exposed to ultraviolet or violet radiation.
18. The copolymer of claim 17 , wherein the green emission has a wavelength of peak emission of about 490 nm to about 570 nm.
19. The copolymer of claim 17 , wherein the ultraviolet or violet radiation has a peak wavelength of about 350 nm to about 450 nm.
20. The copolymer of claim 1 , wherein the copolymer has a weight average molecular weight of at least about 1,000 Da.
21. A method of making a copolymer, the method comprising:
forming a composition comprising an oxidizing agent, at least one optionally substituted pyrrole monomer, and at least one optionally substituted fluoranthene monomer; and
maintaining the composition under conditions effective to polymerize the pyrrole monomer and fluoranthene monomer to form the copolymer.
22. The method of claim 21 , wherein the molar ratio of the pyrrole monomer to the fluoranthene monomer is about 70:30 to about 1:99.
23. The method of claims 21 , wherein the molar ratio of the oxidizing agent to a total amount of monomer components in the composition is no more than about 3:1.
24. The method of claim 21 , wherein the composition is maintained at a temperature of about 30° C. to about 70° C.
25. The method of claim 21 , wherein forming the composition comprises combining (a) a first solution comprising a first solvent and the oxidizing agent and (b) a second solution comprising a second solvent, the pyrrole monomer, and the fluoranthene monomer, wherein:
the first solvent is at least partially immiscible in the second solvent;
the oxidizing agent is soluble in the first solvent; and
both the pyrrole monomer and the fluoranthene monomer are soluble in both the first and second solvents.
26. An apparatus comprising:
a light source configured to emit an ultraviolet or violet radiation; and
a composition configured to receive at least a portion of the radiation emitted from the light source, wherein the composition comprises a copolymer comprising at least one optionally substituted fluoranthene as a first monomer unit and at least one optionally substituted pyrrole as a second monomer unit.
27. The apparatus of claim 26 , further comprising a light detector configured to measure light emitted from the composition.
28. The apparatus of claim 27 , further comprising a housing, wherein the housing contains the composition and is configured to receive a sample adjacent to the composition.
29. An organic light-emitting diode comprising:
a light-emitting active layer;
a conducting layer on one side of the light-emitting active layer;
a cathode; and
an anode, wherein the light-emitting active layer and conducting layer are disposed between the cathode and the anode, and the light-emitting active layer comprises a copolymer comprising at least one optionally substituted fluoranthene as a first monomer unit and at least one optionally substituted pyrrole as a second monomer unit.
30. A method of producing light comprising exposing a composition to a violet or ultraviolet radiation, wherein the composition comprises a copolymer comprising at least one optionally substituted fluoranthene as a first monomer unit and at least one optionally substituted pyrrole as a second monomer unit.
31. A method for detecting nitroaromatics within a sample, the method comprising:
providing a sample suspected of containing one or more nitroaromatics;
contacting a composition to the sample, wherein the composition comprises a copolymer comprising at least one optionally substituted fluoranthene as a first monomer unit and at least one optionally substituted pyrrole as a second monomer unit;
exposing the composition to a radiation effective to produce fluorescence from the copolymer; and
measuring the amount of fluorescence produced by the copolymer.
32. The method of claim 31 , wherein the produced fluorescence is greater in the absence of nitroaromatics than in the presence of nitroaromatics.