IP Library Granted Patent US 10,444,249
Granted Patent B2
US 10,444,249 · App. 14/908,954 · Granted Oct 15, 2019

Ion sensor

Inventors: Takanori Fukushima (Yokohama, JP); Fumitaka Ishiwari (Yokohama, JP); Hanako Hasebe (Yokohama, JP); Takao Someya (Bunkyo-ku, JP); Tsuyoshi Sekitani (Bunkyo-ku, JP)
Assignee: JAPAN SCIENCE AND TECHNOLOGY AGENCY
G01N33/84C07C69/017C07C69/54C07C219/34C08F220/06C08F220/30C08F220/34G01N21/6428G01N31/22
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,444,249
App. No.
14/908,954
Granted
Oct 15, 2019
Kind
B2
Abstract

Provided is a compound including a repeating unit (A) having a carboxyl group on a side chain thereof and a repeating unit (B) having a carboxylate group having an ester residue exhibiting an aggregation-induced emission capability on a side chain thereof and the compound is useful as a polyvalent metal ion sensor such as calcium ions that is capable of reversible sensing and of being integrated into a device.

Claims (22)

1. A copolymer, comprising a repeating unit (A) comprising a carboxyl group on a side chain thereof, and a repeating unit (B) comprising a carboxylate group having an ester residue exhibiting an aggregation-induced emission capability on a side chain thereof,

wherein the repeating unit (A) is a repeating unit derived from a monomer selected from the group consisting of acrylic acid, methacrylic acid and styrenecarboxylic acid;

wherein the repeating unit (B) is a repeating unit derived from at least one monomer selected from the group consisting of an acrylate, a methacrylate and a styrenecarboxylate; and

wherein the ester residue is derived from 1-methyl-1,2,3,4,5-pentaphenylsilole, 2,3,4,5-tetraphenyl-1,1-dimethylsilole or tetraphenylethylene, each of which optionally have 1 to 5 hydrophilic groups substituted on a phenyl group thereof, wherein the hydrophilic groups are independently selected from the group consisting of hydroxy group, an amino group, an alkylamino group, a dialkylamino group, a thiol group, a polyoxyethylene group, a polyoxypropylene group and a sulfinyl group.

2. The copolymer according to claim 1 , wherein the copolymer has a molar ratio of the repeating unit (A) to the repeating unit (B), (A:B) 4:1 to 1000:1.

3. The copolymer according to claim 1 , wherein the copolymer has a number-average molecular weight of 10,000 to 1,000,000.

4. The copolymer according to claim 1 , wherein the copolymer is a copolymer adapted to function as a polymer for detecting polyvalent metal ion fluorescence.

5. The copolymer according to claim 1 , further comprising a repeating unit (C) derived from a polyfunctional monomer.

6. The copolymer according to claim 5 , wherein the copolymer comprises 0.1 to 10 mol % of the repeating unit (C).

7. The copolymer according to claim 5 , wherein the repeating unit (C) is a repeating unit derived from a monomer having two or more polymerizable vinyl groups.

8. A device for detecting a polyvalent metal ion, the device comprising the copolymer according to claim 1 .

9. The device of claim 8 , wherein the copolymer is immobilized on a solid base material.

10. The device of claim 9 , wherein the copolymer is immobilized on the solid base material by covalent bonding to the solid base material.

11. A method for quantifying a polyvalent metal ion concentration in a sample, the method comprising contacting the sample with the device of claim 8 , and measuring a fluorescence intensity.

12. The copolymer according to claim 1 , wherein the hydrophilic groups are independently selected from a C 1 to C 6 alkylamino group and a di(C 1 to C 6 alkyl)amino group.

13. The copolymer according to claim 1 , wherein the ester residue is derived from 1-methyl-1,2,3,4,5-pentaphenylsilole.

14. The copolymer according to claim 1 , wherein the ester residue is derived from 2,3,4,5-tetraphenyl-1,1-dimethylsilole.

15. The copolymer according to claim 1 , wherein the ester residue is derived from tetraphenylethylene optionally having 1 to 5 hydrophilic groups substituted on a phenyl group thereof, wherein the hydrophilic groups are independently selected from the group consisting of hydroxy group, an amino group, an alkylamino group, a dialkylamino group, a thiol group, a polyoxyethylene group, a polyoxypropylene group and a sulfinyl group.

16. The copolymer according to claim 1 , wherein a carboxyl group in the repeating unit (A) on a side chain is a hydrophilic group having bonding site that can bind to the target polyvalent metal ions.

17. The copolymer according to claim 1 , wherein the repeating unit (A) is acrylic acid.

18. The copolymer according to claim 1 , wherein the repeating unit (A) is methacrylic acid.

19. The copolymer according to claim 1 , wherein the repeating unit (A) is styrenecarboxylic acid.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2016
From: FUKUSHIMA, TAKANORI; ISHIWARI, FUMITAKA; HASEBE, HANAKO; SOMEYA, TAKAO; SEKITANI, TSUYOSHI
To: JAPAN SCIENCE AND TECHNOLOGY AGENCY
Reel/Frame 037623/0739 →
Priority Claims (1)
JP 2013-157754 · Jul 30, 2013 · national
Continuity (1)
Related Publication 20160169920A1 · Jun 16, 2016
Cited By (1)
US 12,320,774