# US 8,465,678 B2 · Emissive polymers and devices incorporating these polymers

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- Number: US 8,465,678 B2
- Document ID: US8465678B2
- Status: Granted
- Kind: B2
- Application number: 13/078,658
- Filed: 2011-04-01
- Published: 2011-07-21
- Granted: 2013-06-18
- Earliest claimed: 1998-05-05
- Assignees: Massachusetts Institute of Technology
- Applicants: Timothy M. Swager; Jye-Shane Yang; Vance Williams; Yijun Miao; Claus G. Lugmair; Igor A. Levitsky; Jinsang Kim; Robert Deans
- Inventors: Timothy M. Swager; Jye-Shane Yang; Vance Williams; Yijun Miao; Claus G. Lugmair; Igor A. Levitsky; Jinsang Kim; Robert Deans
- Web page: https://patentgrep.com/patent/US8465678B2

## CPC

- C08L 101/12: characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity (liquid crystal materials or compositions C09K19/00)
- B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
- C08F 257/02: on to polymers of styrene or alkyl-substituted styrenes
- C08G 61/00: Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule (C08G2/00 - C08G16/00 take precedence)
- C08G 61/10: only aromatic carbon atoms, e.g. polyphenylenes
- 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 9/02: Organic tenebrescent materials
- C09K 11/06: containing organic luminescent materials
- G01N 21/6428: {Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" (in vivo A61B5/00; immunoassay G01N33/53)}
- G01N 21/643: {non-biological material}
- G01N 21/7703: {using reagent-clad optical fibres or optical waveguides (using measurement of total internal reflection or attenuated total reflection G01N21/552; optical fibres or waveguides per se G02B)}
- H10K 10/701: {Organic molecular electronic devices}
- H10K 30/65: Light-sensitive field-effect devices, e.g. phototransistors
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/151: {Copolymers}
- H10K 85/154: {Ladder-type polymers}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- G01N 2021/7786: {Fluorescence}
- H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/30: Coordination compounds
- Y02E 10/549: Organic PV cells
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to a class of luminescent and conductive polymer compositions having chromophores, and particularly solid films of these compositions exhibiting increased luminescent lifetimes, quantum yields and amplified emissions. These desirable properties can be provided through polymers having rigid groups designed to prevent polymer reorganization, aggregation or π-stacking upon solidification. These polymers can also display an unusually high stability with respect to solvent and heat exposures. The invention also relates to a sensor and a method for sensing an analyte through the luminescent and conductive properties of these polymers. Analytes can be sensed by activation of a chromophore at a polymer surface. Analytes include aromatics, phosphate ester groups and in particular explosives and chemical warfare agents in a gaseous state. The present invention also relates to devices and methods for amplifying emissions by incorporating a polymer having an energy migration pathway and/or providing the polymer as a block co-polymer or as a multi-layer.

## Claims

### Claim 1

An amplification device, comprising:
a pi-conjugated polymer having an energy migration pathway that transports an excitation energy of the polymer upon exposure of the polymer to electromagnetic radiation, and a chromophore covalently attached to the polymer and in electronic communication with the energy migration pathway, wherein the chromophore emits an emission of radiation greater than that emitted from an essentially identical chromophore associated with a polymer that is free of an energy migration pathway, under essentially identical conditions;
a source of energy applicable to the polymer to cause the emission of radiation; and
a detector positioned to detect the emission of radiation,
wherein a luminescence characteristic of the chromophore is changed upon interaction of the polymer and/or chromophore with an analyte molecule.

### Claim 2 (depends on 1)

An amplification device of claim 1, wherein the excitation energy is transferred from the energy migration pathway to the chromophore to cause the emission of radiation.

### Claim 3 (depends on 1)

An amplification device of claim 1, wherein the energy migration pathway has a length of about 30 angstroms or greater.

### Claim 4 (depends on 1)

An amplification device of claim 1, wherein the luminescence characteristic is a fluorescence emission.

### Claim 5 (depends on 4)

An amplification device of claim 4, wherein the fluorescence emission is increased in the presence of the analyte molecule.

### Claim 6 (depends on 4)

An amplification device of claim 4, wherein the fluorescence emission is decreased in the presence of the analyte molecule.

### Claim 7 (depends on 1)

An amplification device as in claim 1, wherein the source of energy is electromagnetic radiation, electrical energy, or chemical energy.

### Claim 8 (depends on 1)

An amplification device as in claim 1, wherein the polymer is a polyarylene, polyarylene vinylene, polyarylene ethynylene, or ladder polymer.

### Claim 9

An amplification device, comprising:
a polymer having an energy migration pathway that transports an excitation energy of the polymer upon exposure of the polymer to electromagnetic radiation, wherein the energy migration pathway has a length of about 30 angstroms or greater, and a chromophore in electronic communication with the energy migration pathway, wherein the chromophore emits an emission of radiation greater than that emitted from an essentially identical chromophore associated with a polymer that is free of an energy migration pathway, under essentially identical conditions;
a source of energy applicable to the polymer to cause the emission of radiation; and
a detector positioned to detect the emission of radiation,
wherein a luminescence characteristic of the chromophore is changed upon interaction of the polymer and/or chromophore with an analyte molecule.

### Claim 10 (depends on 9)

An amplification device of claim 9, wherein the excitation energy is transferred from the energy migration pathway to the chromophore to cause the emission of radiation.

### Claim 11 (depends on 9)

An amplification device of claim 9, wherein the energy migration pathway has a length of about 30 angstroms or greater.

### Claim 12 (depends on 9)

An amplification device of claim 9, wherein the chromophore is covalently attached to the polymer.

### Claim 13 (depends on 9)

An amplification device of claim 9, wherein the chromophore is non-covalently associated with the polymer.

### Claim 14 (depends on 9)

An amplification device of claim 9, wherein the luminescence characteristic is a fluorescence emission.

### Claim 15 (depends on 14)

An amplification device of claim 14, wherein the fluorescence emission is increased in the presence of the analyte molecule.

### Claim 16 (depends on 14)

An amplification device of claim 14, wherein the fluorescence emission is decreased in the presence of the analyte molecule.

### Claim 17 (depends on 9)

An amplification device as in claim 9, wherein the source of energy is electromagnetic radiation, electrical energy, or chemical energy.

### Claim 18 (depends on 9)

An amplification device as in claim 9, wherein the polymer is a polyarylene, polyarylene vinylene, polyarylene ethynylene, or ladder polymer.

### Claim 19

An amplification device, comprising:
a polymer having an energy migration pathway that transports an excitation energy of the polymer upon exposure of the polymer to electromagnetic radiation, and a chromophore in electronic communication with the energy migration pathway, wherein the chromophore emits a fluorescence emission greater than that emitted from an essentially identical chromophore associated with a polymer that is free of an energy migration pathway, under essentially identical conditions;
a source of energy applicable to the polymer to cause the fluorescence emission; and
a detector positioned to detect the fluorescence emission,
wherein the fluorescence emission is decreased upon interaction of the polymer and/or chromophore with an analyte molecule.

### Claim 20 (depends on 19)

An amplification device of claim 19, wherein the excitation energy is transferred from the energy migration pathway to the chromophore to cause the emission of radiation.

### Claim 21 (depends on 19)

An amplification device of claim 19, wherein the energy migration pathway has a length of about 30 angstroms or greater.

### Claim 22 (depends on 19)

An amplification device of claim 19, wherein the chromophore is covalently attached to the polymer.

### Claim 23 (depends on 19)

An amplification device of claim 19, wherein the chromophore is non-covalently associated with the polymer.

### Claim 24 (depends on 19)

An amplification device as in claim 19, wherein the source of energy is electromagnetic radiation, electrical energy, or chemical energy.

### Claim 25 (depends on 19)

An amplification device as in claim 19, wherein the polymer is a polyarylene, polyarylene vinylene, polyarylene ethynylene, or ladder polymer.