# US 10,768,154 B2 · Ratiometric quantum dot-rhodamine B sensing compound and device made from the compound

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- Number: US 10,768,154 B2
- Document ID: US10768154B2
- Status: Granted
- Kind: B2
- Application number: 15/464,643
- Filed: 2017-03-21
- Published: 2017-09-21
- Granted: 2020-09-08
- Earliest claimed: 2016-03-21
- Assignees: Colgate-Palmolive Company
- Applicants: Colgate-Palmolive Company
- Inventors: Venda Porter Maloney; Donghui Wu; Long Pan; Preston Snee; Armen Shamirian
- Web page: https://patentgrep.com/patent/US10768154B2

## CPC

- G01N 33/0044: {Sulphides, e.g. H2S}
- C09B 11/24: Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes}
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/06: containing organic luminescent materials
- C09K 11/883: {with zinc or cadmium}
- G01N 33/84: involving inorganic compounds or pH
- 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)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present disclosure is directed to a sensing agent. The sensing agent comprises a quantum dot; and a dye moiety coupled to the quantum dot. The sensing agent is capable of sensing at least one analyte chosen from hydrogen sulfide (H2S) and bisulfide. Sensors made from the sensing agents are also disclosed.

## Claims

### Claim 1

A sensor, comprising:
a support matrix; and
a sensing agent embedded in the support matrix, the sensing agent comprising:
a quantum dot; and
a dye moiety coupled to the quantum dot,
wherein the sensing agent is capable of sensing at least one analyte chosen from hydrogen sulfide by FRET modulation between the quantum dot and the dye moiety, and wherein the sensing agent has the formula
QDX2—R2—S—S—R1—X1—Y)n
wherein:
QD is the quantum dot,
Y is the dye moiety,
wherein the dye moiety is a rhodamine group selected from one of:
where the dotted bond shows the position of attachment to the coupling moiety;
R1 and R2 organic bridging groups that will, in combination with the associated linkages X1 and X2 and disulfide bond (—S—S—), provide a distance between the dye and the QD that is from about 0.1 nm to about 10 nm, and
X1 and X2 are linkages that respectively function to attach the R1 group to the dye and R2 group to the quantum dot;
n is the number of coupling-dye groups attached to the QD;
wherein R1 and R2 are alkyl bridges and X1 and X2 are amide linkages; and
wherein the sensor has a detection limit for bisulfide, in water, of less than 2 μM at a sensor concentration of 3.4×10−9 M as determined by the boot strap method, where the conjugated dye:QD ratio is 1.3:1.

### Claim 2 (depends on 1)

The sensor of claim 1, wherein the sensing agent is capable of exhibiting a ratiometric response to at least one analyte chosen from hydrogen sulfide (H2S) and bisulfide.

### Claim 3 (depends on 1)

The sensor of claim 1, wherein the support matrix is chosen from paper, a polymer and a combination thereof.

### Claim 4 (depends on 1)

The sensor of claim 1, wherein the dye moiety is coupled to the quantum dot via a disulfide bridge coupling moiety that is cleavable by the at least one analyte.

### Claim 5 (depends on 1)

The sensor of claim 1, wherein the quantum dot comprises an emissive material selected from ZnS, ZnSe, ZnSe/ZnS, CdS, CdS/ZnS, CdZnS, CdZnS/ZnS, CdSe, CdZnSe, CdSeS, CdZnSeS, CdSe/ZnS, CdZnSe/ZnS, CdSeS/ZnS, CdZnSeS/ZnS, CdSe/CdZnS, CdZnSe/CdZnS, CdSeS/CdZnS, CdZnSeS/CdZnS, CdTe, CdSeTe, CdTe/ZnS, CdSeTe/ZnS, CdTe/CdZnS, CdSeTe/CdZnS, CdTe/ZnSe, CdSeTe/ZnSe, CdTe/ZnSeS, CdSeTe/ZnSeS, ZnSe/CdS, CdS/ZnSe, ZnSe/CdS/ZnS, CdS/ZnSe/ZnS, CdSe/CdTe, CdTe/CdSe, CdSe/CdTe/ZnS, CdTe/CdSe/ZnS, CdSe/CdTe/ZnSe, CdTe/CdSe/ZnSe, AgInS2, AgInS2/ZnS, CuInS2, CuInS2/ZnS, AgInSe2, AgInSe2/ZnS, CuInSe2, CuInSe2/ZnS, ZnSe:Mn, ZnSe:Mn/ZnS, ZnSe:Cu, ZnSe:Cu/ZnS, ZnSe/ZnMnS/ZnS, CdSe:Ag, CdSe:Ag/ZnS, PbS, PbS/ZnS, PbSe, PbSe/CdSe, PbSe/CdSe/ZnSe, ZnSe/ZnMgS/ZnS, ZnSeMnx/ZnS, CdS/CdxZn(1-x)S, CdSe/CdxZn(1-x)S, CdSexTe(1-x)/CdyZn(1-y)S, AgInS2/ZnS, CuInS2/ZnS, AgInSe2/ZnS, and CuInSe2/ZnS, where x and y range from 0 to 1.

### Claim 6 (depends on 1)

The sensor of claim 1, wherein the quantum dot comprises at least one coating chosen from a phase transfer coating, a ligand exchange coating, a polymer coating and a silanization coating.

### Claim 7 (depends on 1)

The sensor of claim 1, wherein the sensor is selective towards the HS− anion compared to other thiols chosen from glutathione and cysteine.

### Claim 8 (depends on 1)

The sensor of claim 1, wherein the sensor provides for a linear correlation of the integrated emission ratio of the QD:dye as a function of the HS− concentration over a broader range of bisulfide analyte concentrations then the same QD donor and dye acceptor combination without the disulfide bridge.