Composite polydots and applications thereof

Patent metadata

Field	Value
Publication number	US-10512690-B2
Application number	US-201515303171-A
Country	US
Kind code	B2
Filing date	Apr 10, 2015
Priority date	Apr 10, 2014
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

The present invention relates to nanoparticle compositions and, in particular, to composite polymeric nanoparticle compositions. A composite nanoparticle described herein comprises a photoluminescent polymeric component and a photo-thermal polymeric component. The photoluminescent polymeric component and the photo-thermal polymeric component can each comprise a single polymeric species or multiple polymeric species.

First claim

The invention claimed is:

1. A composite nanoparticle comprising:
photoluminescent polymeric component; and
a photo-thermal polymeric component,
wherein the photo-thermal component comprises poly[4,4-bis(2-ethylhexvl)cyclopenta[2,1-b:3,4-b′]dithiophene-2,6-diyl-alt-2,5-diethylhexyl-3,6-bis(thiophen-2-yl)pyrrolor[3,4-c]-pyrrole-1,4-dione].

2. The composite nanoparticle of claim 1 , wherein the photoluminescent polymeric component comprises a polymeric species having a molecular weight lower than a polymeric species of the photo-thermal polymeric component.

3. The composite nanoparticle of claim 1 , wherein the photoluminescent polymeric component comprises a polymeric species having a wider bandgap than a polymeric species of the photo-thermal polymeric component.

4. The composite nanoparticle of claim 2 , wherein the polymeric species of the photoluminescent polymeric component is the same polymeric species as the photo-thermal polymeric component.

5. The composite nanoparticle of claim 1 , wherein the photoluminescent polymeric component and the photo-thermal polymeric component are present throughout the nanoparticle.

6. The composite nanoparticle of claim 1 , wherein the photoluminescent polymeric component and the photo-thermal polymeric component are localized to different regions of the composite nanoparticle.

7. The composite nanoparticle of claim 6 , wherein the photo-thermal polymeric component is localized to the core of the composite nanoparticle and the photoluminescent polymeric component is localized to surfaces of the composite nanoparticle.

8. The composite nanoparticle of claim 7 , wherein the photoluminescent polymeric component forms a shell over the photo-thermal polymeric component.

9. The composite nanoparticle of claim 1 , wherein a ratio of the photo-thermal polymeric component to the photoluminescent polymeric component ranges from 1:10 to 10:1.

10. The composite nanoparticle of claim 1 , wherein the photoluminescent polymeric component comprises one or more species of conjugated polymer operable to photoluminesce in the visible or infrared region of the electromagnetic spectrum.

11. The composite nanoparticle of claim 10 , Wherein the photo-thermal polymeric component comprises one or more species of conjugated polymer operable to generate heat when irradiated with radiation of wavelength 700 nm to 1000 nm.

12. The composite nanoparticle of claim 1 having a size of 1 nm to 500 nm.

13. The composite nanoparticle of claim 11 , wherein the photoluminescent polymeric component comprises polymer species having a donor-acceptor architecture comprising a donor monomeric species (D) and an acceptor monomeric species (A).

14. The composite nanoparticle of claim 13 , wherein the photo-thermal polymeric component comprises polymer species having a donor-acceptor architecture comprising a donor monomeric species (D) and an acceptor monomeric species (A).

15. The composite nanoparticle of claim 14 , wherein the donor-acceptor architecture is of the formula

wherein D is a donor monomeric species, A and A 1 are an acceptor monomeric species, m and n range from 1 to 100 and each X is independently O, N, S, Se or Te.

16. The composite nanoparticle of claim 15 , wherein the donor-acceptor architecture is of the formula

17. The composite nanoparticle of claim 1 , wherein the photothermal polymeric component comprises poly [4,4-bis(2-ethylhexyl)-cyclopenta[2,1-b;3,4-b ′]dithiophene-2,6-diylalt-2,1,3-benzoselenadiazole-4,7-diyl], and the photoluminescent component comprises poly[(9,9-dihexylfluorene)-co-2,1,3-benzothiadiazole-co-4,7-di(thiophen-2-yl)-,1,3-benzothiadiazole.

18. The composite nanoparticle of claim 17 , wherein the poly [4,4-bis(2-ethylhexyl)-cyclopenta[2,1-b ;3,4 -b′]dithiophene-2,6-diylalt-2,1,3-benzoselenadiazole-4,7-diyl]has a molecular weight ranging from 20,000 to 35,000 Da.

19. The composite nanoparticle of claim 1 , wherein the polymeric photoluminescent component is substituted with an oligomeric photoluminescent component.

20. The composite nanoparticle of claim 19 , wherein the oligomeric photoluminescent component comprises oligomeric [(9,9-dihexylfluorene)-co-2,1,3-benzothiadiazole-co-4,7-di(thiophen-2-yl)-2,1,3-benzothiadiazole.

21. The composite nanoparticle of claim 1 further comprising one or more active agents associated with the photoluminescent polymeric component, the photo-thermal polymeric component or both.

22. The composite nanoparticle of claim 21 , wherein the one or more active agents comprise an antibody, a chemokines receptor, a targeting ligand, protein, amino acid or nucleic acid.

23. A composition comprising:
an aqueous or aqueous-based medium; and
composite nanoparticles disposed in the aqueous or aqueous-based medium, the nanoparticles comprising a photoluminescent polymeric component and a photo-thermal polymeric component,
wherein the photo-thermal component comprises poly[4,4-bis(2-ethylhexyl)cyclopenta[2,1-b;3,4-b′]dithiophene-2,6-diyl-alt-2,5-diethylhexyl-3,6-bis(thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione].

24. The composition of claim 23 , wherein the nanoparticles are present in the aqueous or aqueous-based medium an amount of 1 fg/mL to greater than 1 mg/mL.

25. The composition of claim 23 , wherein the nanoparticles are present in the aqueous or aqueous-based medium an amount of 5 μg/mL to 100 μg/mL.

26. The composition of claim 23 , wherein the photoluminescent polymeric component comprises a polymeric species having a molecular weight lower than a polymeric species of the photo-thermal polymeric component.

27. The composition of claim 23 , wherein the photoluminescent polymeric component and the photo-thermal polymeric component are present throughout the nanoparticle.

28. The composition of claim 23 , wherein the photoluminescent polymeric component and the photo-thermal polymeric component are localized to different regions of the composite nanoparticle.

29. The composition of claim 28 , wherein the photo-thermal polymeric component is localized to the core of the composite nanoparticle and the photoluminescent polymeric component is localized to surfaces of the composite nanoparticle.

30. The composition of claim 23 , wherein the ratio of photo-thermal polymeric component to the photoluminescent polymeric component ranges from 1:10 to 10:1.

31. The composition of claim 23 , wherein the photoluminescent polymeric component comprises polymer species having a donor-acceptor architecture comprising a donor monomeric species (D) and an acceptor monomeric species (A).

32. The composition of claim 31 , wherein the photo-thermal polymeric component comprises polymer species having a donor-acceptor architecture comprising a donor monomeric species (D) and an acceptor monomeric species (A).

33. The composition of claim 32 , wherein the donor-acceptor architecture is of the formula

wherein D is a donor monomeric species, A and A 1 are an acceptor monomeric species, m and n rang

Assignees

• Univ Wake Forest

Inventors

• Levi Nicole Hope
• Macneill Christopher Michael
• Gurysh Elizabeth Grace
• Argenta Louis Charles

Classifications

• C09K2211/1483

  containing nitrogen and sulfur as heteroatoms · CPC title

• C09K2211/1466

  containing nitrogen as the only heteroatom · CPC title

• C09K2211/1458

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1416

  Condensed systems · CPC title

• C08G2261/96

  coating of particles · CPC title