Sensor dyes for real-time sensing of metal ions in aqueous environments

Patent metadata

Field	Value
Publication number	US-11275071-B2
Application number	US-201615767175-A
Country	US
Kind code	B2
Filing date	Oct 14, 2016
Priority date	Oct 14, 2015
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

Sensors for detecting and distinguishing metals in a sample comprise phenol group-containing azo dyes, the phenol group having one hydroxy involved in reversible metal ion binding and a second hydroxy alkylated to an optically transparent substrate. The sensors have utility for detecting chromium, calcium, magnesium, copper, mercury, nickel, zinc, cobalt, manganese, cadmium, lead, tin, aluminum, potassium, sodium, or arsenic ions in a sample.

First claim

What is claimed is:

1. A sensor comprising a panel, the panel comprising an optically transparent substrate and more than one dye of formula (IV) bound to the optically transparent substrate by a covalent linkage alkylated on a phenol group of the more than one dye of formula (IV), wherein each phenol group of the more than one dye of formula (IV) has a hydroxy involved in metal binding and a second hydroxy and is alkylated on the second hydroxy; wherein the dye of formula (IV) reversibly binds at least one metal ion;
A-B  (IV)

wherein A is selected from the group consisting of:

B is selected from the group consisting of:

and
R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of:

2. The sensor of claim 1 , wherein the more than one dye of formula (IV) are different.

3. The sensor of claim 1 , wherein the panel is an array comprising more than one optically transparent substrate; wherein each optically transparent substrate is covalently bound to a dye capable of sensing more than one metal covalently bound to the substrate.

4. The sensor of claim 1 , wherein the more than one dye of formula (IV) is selected from the group consisting of
4-(2-pyridylazo)resorcinol (PAR), 4-(quinolin-8-yldiazenyl)benzene-1,3-diol (QAR),

5. The sensor of claim 1 , wherein the optically transparent substrate is a polymer.

6. The sensor of claim 5 , wherein the polymer comprises cellulose, crosslinked polymethacrylate ester, polyacrylamide, or crosslinked polyethylene glycol.

7. The sensor of claim 5 , wherein the polymer is a synthetic polymer.

8. The sensor of claim 7 , wherein the polymer comprises crosslinked polymethacrylate ester, polyacrylamide, or crosslinked polyethylene glycol.

9. The sensor of claim 7 , wherein the polymer comprises poly(acrylate)s, poly(methylmethacrylate), or poly(hydroxyethylmethacrylate).

10. The sensor of claim 1 , wherein the optically transparent substrate further comprises a perturbation moiety.

11. The sensor of claim 10 , wherein the perturbation moiety is a cation, an anion or a zwitterion or a neutral species.

12. The sensor of claim 11 , wherein the cation comprises trialkylammonium groups.

Assignees

• Uwm Res Foundation Inc

Inventors

• Schwabacher Alan
• Geissinger Peter
• Hagemann Trevor
• Oehm Sarah
• Fenske Tyler G

Classifications

• C09B29/3665

  containing a six-membered heterocyclic ring with two nitrogen atoms · CPC title

• G01N31/22

  using chemical indicators (G01N31/02 takes precedence) · CPC title

• C09B56/00

  Azo dyes containing other chromophoric systems · CPC title

• G01N33/1813 Primary

  Specific cations in water, e.g. heavy metals · CPC title

• C09B29/0811

  further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino · CPC title