# US 11,307,158 B1 · Nanoparticles for chemiresistor sensors

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- Number: US 11,307,158 B1
- Document ID: US11307158B1
- Status: Granted
- Kind: B1
- Application number: 17/495,499
- Filed: 2021-10-06
- Granted: 2022-04-19
- Earliest claimed: 2021-10-06
- Assignees: Nanoscent Ltd.
- Applicants: Nanoscent Ltd.
- Inventors: Yair Pasca; Katya Kapilov; Maayan Hirsch; Sima Israel; Yahel Zanti
- Web page: https://patentgrep.com/patent/US11307158B1

## CPC

- G01N 27/127: {comprising nanoparticles}
- G01N 33/0047: {Organic compounds}
- B82Y 15/00: Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
- 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)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES

## Abstract

A nanoparticle characterized by sensitivity to an analyte of interest, and comprising a conductive core in contact with a plurality of ligands bound to the conductive core is disclosed. Additionally, a chemiresistor sensor comprising the nanoparticles of the invention and a method of using thereof such as for detection of an analyte of interest in a gaseous sample are disclosed.

## Claims

### Claim 1

A nanoparticle, comprising a conductive core in contact with a plurality of ligands bound to said core, wherein:
each ligand comprises a first moiety thereof capable of binding to the core and a second moiety covalently bound to said first moiety;
wherein the second moiety is an alkyl-aryl moiety comprising at least 2 aliphatic carbon atoms
and the plurality of ligands are assembled to form a shell on top of said core;
and wherein said nanoparticle is characterized by sensitivity to an analyte of interest.

### Claim 2 (depends on 1)

The nanoparticle of claim 1, wherein each of the plurality of ligands is bound to the core via the first moiety, and wherein said bound is via a covalent bond and wherein the covalent bond comprises a coordinative bond.

### Claim 3 (depends on 1)

The nanoparticle of claim 1, wherein each core independently comprises a transitional metal, optionally wherein the transitional metal is substantially in an elemental state within said core.

### Claim 4 (depends on 1)

The nanoparticle of claim 1, wherein the ligand is represented by Formula 1:
wherein:
R represents the first moiety;
each R1 independently represents a substituent or H;
each X and X1 independently represents a heteroatom, —CHR1-, —CR1R1-, or is absent;
A represents an optionally substituted aryl, an optionally substituted heteroaryl, a polycyclic aryl or any combination thereof;
n and k are integers each independently ranging from 0 to 5; and
m is an integer ranging from 1 to 5.

### Claim 5 (depends on 4)

The nanoparticle of claim 4, wherein said heteroatom is selected from the group consisting of O, S, NH, NR1, PH and PR1 or a combination thereof; and if X1 represents the heteroatom then k ranges between 1 and 5.

### Claim 6 (depends on 1)

The nanoparticle of claim 1, wherein the first moiety comprises thio, carboxy, carbonyl, amino, hydroxy, amide, optionally substituted disulfide, silyl, diazo, heteroaryl, an olefin, phosphate, silyl, phosphine, including any salts, any derivative or any combination thereof.

### Claim 7 (depends on 1)

The nanoparticle of claim 1, wherein said first moiety comprises thio or thiolate, and wherein the alkyl-aryl moiety is represented by Formula 2:
wherein:
each R1 independently represents a substituent or H;
each X and X1 independently represents a heteroatom, or is absent;
A represents an optionally substituted aryl, an optionally substituted heteroaryl, or any combination thereof the dashed line represents an attachment point to the first moiety;
the heteroatom is selected from the group consisting of O, S, NH, and NR1, or a combination thereof;
n is an integer each independently being 0 or 1;
k is an integer ranging from 0 to 5;
m is an integer ranging from 1 to 5; and if X1 represents the heteroatom then k ranges between 1 and 5.

### Claim 8 (depends on 7)

The nanoparticle of claim 7, wherein m and k each independently is 1 or 2.

### Claim 9 (depends on 1)

The nanoparticle of claim 1, wherein the alkyl-aryl moiety comprises an aryl substituted in meta-, or in para-position.

### Claim 10 (depends on 1)

The nanoparticle of claim 1, wherein the alkyl-aryl moiety is represented by Formula 3:
wherein m is 2, and wherein k is between 1 and 3.

### Claim 11 (depends on 1)

The nanoparticle of claim 1, wherein the ligand comprises at least one of:
wherein L comprises ethyl or butyl.

### Claim 12 (depends on 7)

The nanoparticle of claim 7, wherein said substituent comprises one or more substituents, each independently selected from the group consisting of: C1-C6 alkyl, halo, —NO2, —CN, —OH, —NH2, carbonyl, —CONH2, —CONR′2, —CNNR2, —CSNR2, —CONH—OH, —CONH—NH2, —NHCOR′, —NHCSR′, —NHCNR′, —NC(═O)OR′, —NC(═O)NR′, —NC(═S)OR′, —NC(═S)NR′, —SO2R′, —SOR′, —SR′, —SO2OR′, —SO2N(R′)2, —NHNR′2, —NNR′, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, C1-C6 alkoxy, C1-C6 haloalkoxy, hydroxy(C1-C6 alkyl), hydroxy(C1-C6 alkoxy), alkoxy(C1-C6 alkyl), alkoxy(C1-C6 alkoxy), amino(C1-C6 alkyl), —CONH(C1-C6 alkyl), —CON(C1-C6 alkyl)2, —CO2H, —CO2R′, —OCOR′, —OCOR′, —OC(═O)OR′, —OC(═O)NR′, —OC(═S)OR′, —OC(═S)NR′, a heteroatom, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, or a combination thereof, wherein each R′ is independently selected from hydrogen, alkyl, alkenyl, aryl, heteroaryl a heteroatom, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, or any combination thereof.

### Claim 13 (depends on 1)

The nanoparticle of claim 1, wherein said analyte of interest is a volatile organic compound (VOC) selected from an optionally unsaturated C1-C20 aldehyde, and an optionally unsaturated C1-C20alkane, or both.

### Claim 14

A chemiresistor sensor comprising:
at least two electrodes; and
a sensing element electrically connected to the two electrodes and comprising a structure made from a plurality of nanoparticles, wherein:
each nanoparticle comprises a metal core in contact with a plurality of ligands bound to said core;
each ligand comprises a first moiety or a salt thereof capable of binding to the core, and an alkyl-aryl moiety covalently bound to said first moiety;
the plurality of ligands are assembled to form a shell on top of said core;
and wherein said nanoparticle is characterized by sensitivity to an analyte of interest comprising a volatile organic compound (VOC) selected from an optionally unsaturated C1-C20 aldehyde, and an optionally unsaturated C1-C20alkane.

### Claim 15 (depends on 14)

The chemiresistor sensor of claim 14, wherein the first moiety comprises thio or thiolate, and wherein the alkyl-aryl moiety is represented by Formula 2:
wherein:
each R1 independently represents a substituent or H;
each X and X1 independently represents a heteroatom, or is absent;
A represents an optionally substituted aryl, an optionally substituted heteroaryl, or any combination thereof; the dashed line represents an attachment point to the first moiety;
the heteroatom is selected from the group consisting of O, S, NH, and NR1, or a combination thereof;
n is an integer each independently being 0 or 1;
k is an integer ranging from 0 to 5;
m is an integer ranging from 1 to 5; and if X1 represents the heteroatom then k ranges between 1 and 5.

### Claim 16 (depends on 14)

The chemiresistor sensor of claim 14, wherein the ligand comprises at least one of:
wherein L comprises ethyl or butyl.

### Claim 17 (depends on 14)

The chemiresistor sensor of claim 14, wherein the sensor is configured for selective detection of the analyte of interest within a gaseous sample, wherein a concentration of the analyte of interest within the sample is between 1 ppb and 1 ppm.

### Claim 18 (depends on 14)

A method for detection of an analyte of interest in a gaseous sample, comprising:
a. exposing the chemiresistor sensor of claim 14 to the sample comprises a plurality of VOCs;
b. providing electricity to the sensor, so as to obtain a plurality of conductivity values generated by the sensor; and
c. analyzing said conductivity values, thereby determining the presence of the analyte of interest within said sample, wherein the analyte of interest comprises a VOC selected from an aldehyde, an alkane or both.

### Claim 19 (depends on 18)

The method of claim 18, wherein the analyzing step further comprises determining a concentration of the analyte of interest within the sample.

### Claim 20 (depends on 18)

The method of claim 18, wherein a concentration of the analyte of interest within the sample is between 1 ppb and 1 ppm.