Chromophoric polymer dots
The present invention provides, among other aspects, stabilized chromophoric nanoparticles. In certain embodiments, the chromophoric nanoparticles provided herein are rationally functionalized with a pre-determined number of functional groups. In certain embodiments, the stable chromophoric nanoparticles provided herein are modified with a low density of functional groups. In yet other embodiments, the chromophoric nanoparticles provided herein are conjugated to one or more molecules. Also provided herein are methods for making rationally functionalized chromophoric nanoparticles.
1. A chromophoric nanoparticle comprising a semiconducting polymer having a plurality of monomeric units, wherein less than 50% of the monomeric units present in the chromophoric nanoparticle are covalently modified with a hydrophilic moiety, wherein at least one of the monomeric units is covalently modified with a hydrophilic functional group suitable for conjugation, wherein at least one of the monomeric units comprises fluorene or a fluorene derivative, and wherein the hydrophilic functional group is independently selected from the group consisting of carboxylic acid or salts thereof, amino, mercapto, aldehyde, ester, carbonyl, phosphate, cyanate, succinimidyl ester, maleimide, and substituted derivatives thereof.
2. The chromophoric nanoparticle of claim 1 , wherein the hydrophilic functional group is suitable for bioconjugation.
3. The chromophoric nanoparticle of claim 2 , wherein the hydrophilic functional group is stable in an aqueous solution.
4. The chromophoric nanoparticle of claim 1 , wherein less than 30% of the monomeric units are covalently modified with the hydrophilic moiety.
5. The chromophoric nanoparticle of claim 1 , wherein less than 20% of the monomeric units are covalently modified with the hydrophilic moiety.
6. The chromophoric nanoparticle of claim 1 , wherein less than 15% of the monomeric units are covalently modified with the hydrophilic moiety.
7. The chromophoric nanoparticle of claim 1 , wherein at least one of the monomeric units is covalently modified with a nonionic, non-reactive hydrophilic moiety or an ionic, non-reactive hydrophilic moiety.
8. The chromophoric nanoparticle of claim 1 , wherein the chromophoric nanoparticle comprises a plurality of semiconducting polymers.
9. The chromophoric nanoparticle of claim 8 , wherein the chromophoric nanoparticle comprises a blend of semiconducting polymers.
10. The chromophoric nanoparticle of claim 8 , wherein the chromophoric nanoparticle comprises a blend of semiconducting polymers and non-semiconducting polymers.
11. The chromophoric nanoparticle of claim 1 , wherein the chromophoric nanoparticle is stable for at least 3 months when stored in an aqueous solution.
12. The chromophoric nanoparticle of claim 11 , wherein the chromophoric nanoparticle is stable for at least 4 months when stored in an aqueous solution.
13. The chromophoric nanoparticle of claim 12 , wherein the chromophoric nanoparticle is stable for at least 6 months when stored in an aqueous solution.
14. The chromophoric nanoparticle according to claim 1 , wherein the chromophoric nanoparticle is formed by a nanoprecipitation of one or more chromophoric polymers.
15. A composition comprising a plurality of chromophoric nanoparticles according to claim 1 .
16. The composition of claim 15 , comprising a homogeneous population of chromophoric nanoparticles.
17. The chromophoric nanoparticle of claim 1 , wherein less than 10% of the monomeric units are covalently modified with the hydrophilic moiety.
18. The chromophoric nanoparticle of claim 1 , wherein less than 7% of the monomeric units are covalently modified with the hydrophilic moiety.
19. A chromophoric nanoparticle comprising a semiconducting polymer having a plurality of monomeric units, wherein less than 50% of the monomeric units present in the chromophoric nanoparticle are covalently modified with a hydrophilic moiety, and wherein at least one side chain of the monomeric units is covalently modified with a hydrophilic functional group suitable for conjugation, and wherein at least one of the monomeric units comprises fluorene or a fluorene derivative.
20. The chromophoric nanoparticle of claim 1 , wherein the hydrophilic functional group is covalently bonded to a backbone, a side chain, a terminal unit of the semiconducting polymer, or a combination thereof.
21. The chromophoric nanoparticle of claim 19 , further comprising one or more hydrophilic functional groups located at a terminal unit of the semiconducting polymer.
22. The chromophoric nanoparticle of claim 19 , wherein the hydrophilic functional group is suitable for bioconjugation.
23. The chromophoric nanoparticle of claim 19 , wherein the hydrophilic functional group is stable in an aqueous solution.
24. The chromophoric nanoparticle of claim 19 , wherein less than 30%, less than 25%, less than 15%, less than 10%, or less than 7% of the monomeric units are covalently modified with the hydrophilic moiety.
25. The chromophoric nanoparticle of claim 19 , wherein the hydrophilic functional group is independently selected from the group consisting of carboxylic acid or salts thereof, amino, mercapto, aldehyde, ester, hydroxyl, carbonyl, phosphate, cyanate, succinimidyl ester, maleimide, and substituted derivatives thereof.
26. The chromophoric nanoparticle of claim 19 , wherein at least one of the monomeric units is covalently modified with a nonionic, non-reactive hydrophilic moiety or an ionic, non-reactive hydrophilic moiety.
27. The chromophoric nanoparticle of claim 19 , wherein the chromophoric nanoparticle comprises a plurality of semiconducting polymers.
28. The chromophoric nanoparticle of claim 27 , wherein the chromophoric nanoparticle comprises a blend of semiconducting polymers.
29. The chromophoric nanoparticle of claim 27 , wherein the chromophoric nanoparticle comprises a blend of semiconducting polymers and non-semiconducting polymers.
30. The chromophoric nanoparticle of claim 19 , wherein the chromophoric nanoparticle is stable for at least 3 months, at least 4 months, or at least 6 months when stored in an aqueous solution.