# US 10,502,733 B2 · Hybrid semiconducting polymer nanoparticles as polarization-sensitive fluorescent probes

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- Number: US 10,502,733 B2
- Document ID: US10502733B2
- Status: Granted
- Kind: B2
- Application number: 14/903,801
- Filed: 2014-07-08
- Published: 2016-06-09
- Granted: 2019-12-10
- Earliest claimed: 2013-07-08
- Assignees: University of Washington through its Center for Commercialization
- Applicants: University of Washington through its Center for Commercialization
- Inventors: Daniel T. Chiu; Maxwell Zeigler
- Web page: https://patentgrep.com/patent/US10502733B2

## CPC

- G01N 33/54346: {Nanoparticles}
- C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers
- C09K 11/06: containing organic luminescent materials
- G01N 33/587: {Nanoparticles}
- B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites
- C08G 2261/124: alternating
- C08G 2261/1412: Saturated aliphatic units
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3246: containing nitrogen and sulfur as heteroatoms
- C08G 2261/522: fluorescent
- C08G 2261/94: Applications in sensors, e.g. biosensors
- C08L 2205/02: containing two or more polymers of the same C08L -group
- C09K 2211/1416: Condensed systems
- C09K 2211/1425: Non-condensed systems
- C09K 2211/1483: containing nitrogen and sulfur as heteroatoms
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Compositions of, methods of making, and methods of using hybrid nanoparticles comprise at least one semiconducting polymer and at least one nonsemiconducting polymer. Compositions of, methods of making and methods of using hybrid nanoparticles comprise at least one semiconducting polymer and non-semiconducting polymers wherein the non-semiconducting polymer comprises more than one non-semiconducting polymer such that at least one non-semiconducting polymer is functionalized for bioconjugation. The hybrid nanoparticles are polarization-sensitive and have low mass ratios with large fluorescence.

## Claims

### Claim 1

A polarization-sensitive nanoparticle comprising:
a semiconducting chromophoric polymer; and
a matrix, wherein the matrix comprises:
a first non-semiconducting matrix polymer; and
a second non-semiconducting matrix polymer;
wherein:
the nanoparticle comprises a blend of the first non-semiconducting matrix polymer, the second non-semiconducting matrix polymer, and the semiconducting chromophoric polymer;
the polarization-sensitive nanoparticle has at least one critical dimension of 1 nm to 1000 nm; and
the percent of semiconducting chromophoric polymer mass is about 1% to 5% of the total mass of the nanoparticle.

### Claim 2 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the semiconducting chromophoric polymer is luminescent.

### Claim 3 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the semiconducting chromophoric polymer is hydrophobic.

### Claim 4 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the first non-semiconducting matrix polymer is an amphiphilic polymer.

### Claim 5 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the first non-semiconducting matrix polymer comprises a first functional group capable of conjugation.

### Claim 6 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the second non-semiconducting matrix polymer is an amphiphilic polymer.

### Claim 7 (depends on 5)

The polarization-sensitive nanoparticle of claim 5, wherein the second non-semiconducting matrix polymer further comprises a second functional group capable of conjugation.

### Claim 8 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the first non-semiconducting matrix polymer and the second non-semiconducting matrix polymer are the same.

### Claim 9 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the polarization-sensitive nanoparticle is fluorescent.

### Claim 10 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the polarization-sensitive nanoparticle is conjugated to a binding moiety and wherein the binding moiety is configured to bind to a target.

### Claim 11 (depends on 10)

The polarization-sensitive nanoparticle of claim 10, wherein the target is a biomolecule.

### Claim 12 (depends on 10)

The polarization-sensitive nanoparticle of claim 10, wherein the target is a biomarker.

### Claim 13 (depends on 7)

The polarization-sensitive nanoparticle of claim 7, wherein the first functional group, the second functional group, or a combination thereof are suitable for bioconjugation.

### Claim 14

A method of analyzing a target, the method comprising:
binding a polarization-sensitive nanoparticle to the target;
illuminating the nanoparticle with electromagnetic radiation sufficient to produce a florescence signal; and
detecting the fluorescence signal;
wherein the nanoparticle comprises:
a semiconducting chromophoric polymer; and
a matrix, wherein the matrix comprises:
a first non-semiconducting matrix polymer; and
a second non-semiconducting matrix polymer;
wherein the nanoparticle has at least one critical dimension of 1 nm to 1000 nm; and
the percent of semiconducting chromophoric polymer mass is about 1% to 5% of the total mass of the nanoparticle.

### Claim 15 (depends on 14)

The method of claim 14, wherein the electromagnetic radiation is polarized.

### Claim 16 (depends on 14)

The method of claim 14, further comprising detecting a change in the fluorescence signal while analyzing the target.

### Claim 17 (depends on 14)

The method of claim 14, further comprising detecting the orientation of the target from the change in the fluorescence signal.

### Claim 18 (depends on 14)

The method of claim 14, further comprising imaging a target.

### Claim 19 (depends on 14)

The method of claim 14, wherein the target is a biomolecule.

### Claim 20 (depends on 14)

The method of claim 14, wherein the target is a biomarker.

### Claim 21 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the polarization-sensitive nanoparticle has a full width at half maximum of the fluorescence emission peak of less than 60 nm.

### Claim 22 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the semiconducting chromophoric polymer is immobilized within the matrix.

### Claim 23 (depends on 1)

The polarization-sensitive nanoparticle of claim 1, wherein the nanoparticle is conjugated to an antibody, a protein, a nucleic acid, a streptavidin, a peptide, an aptamer, an enzyme, a carbohydrate, a deoxyribonucleic acid, a ribonucleic acid, or a lipid.

### Claim 24 (depends on 14)

The polarization-sensitive nanoparticle of claim 14, wherein the semiconducting chromophoric polymer is immobilized within the matrix.