# US 12,763,363 B2 · Multifunctionalized thiol conductor compound and method for making same

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- Number: US 12,763,363 B2
- Document ID: US12763363B2
- Status: Granted
- Kind: B2
- Application number: 18/357,342
- Filed: 2023-07-24
- Published: 2024-02-08
- Granted: 2026-10-13
- Earliest claimed: 2022-08-01
- Assignees: Blue Solutions Canada Inc.
- Applicants: Blue Solutions Canada Inc.; Capacitor Sciences Incorporated
- Inventors: Qiujie Zhao; Siwei Liang; Jin Yang; Sarah Degras; Patrick Leblanc
- Web page: https://patentgrep.com/patent/US12763363B2

## CPC

- H01M 10/0565: Polymeric materials, e.g. gel-type or solid-type
- C07C 311/48: having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 2300/0082: Organic polymers
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present technology relates to multifunctionalized thiol conductor compounds which can be grafted onto polymers, and methods for making same. In certain embodiments, the compounds of the present technology can be grafted onto polymers having low Tg to synthesize single-ion conducting polymer electrolytes having improved conductivity. The multifunctionalized thiol conductor compounds of the present technology generally comprise more than one sulfonamide anion covalently attached to a substitutable core (A) via a sulphide bond, a thiol functional group and optionally a hydrocarbon side chain (L) attached to the substitutable core (A).

## Claims

### Claim 1

A multifunctionalized thiol conductor compound having formula I:
wherein:
A is a substitutable core;
L is absent or present and when present is an alkyl group, a fluorinated alkyl group, a branched alkyl group, an ethylene oxide group, a fluorinated ethylene oxide group, a cycloalkyl group, a fluorinated cycloalkyl group, a phenyl group, or a fluorinated phenyl group;
Rf is F, CF3, CF2CF3, (CH2)NCF3 wherein N is >1, C6F5, a branched C3-C4 fluoroalkyl group, —(CF2CF2O)m—CF2CF3 wherein m=1, 2 or 3, —(CF2O) p/(CF2CF2O) q-CF2CF3 wherein 1≤p≤10, 13q≤10, and the (CF2O) and (CF2CF2O) units are randomly copolymerized, or an aryl substituted with at least one fluorine, and at least one electron-withdrawing group;
M+ is a monovalent cation;
L1 are each independently absent or present and when present are each independently an alkyl group, a fluorinated alkyl group, a branched alkyl group, an ethylene oxide group, a fluorinated ethylene oxide group, a cycloalkyl group, a fluorinated cycloalkyl group, a phenyl group, or a fluorinated phenyl group;
L2 are each independently absent or present and when present are each independently an alkyl group, a fluorinated alkyl group, a branched alkyl group, an ethylene oxide group, a fluorinated ethylene oxide group, a cycloalkyl group, a fluorinated cycloalkyl group, a phenyl group, or a fluorinated phenyl group;
L3 are each independently absent or present and when present are each independently an alkyl group, a fluorinated alkyl group, a branched alkyl group, an ethylene oxide group, a fluorinated ethylene oxide group, a cycloalkyl group, a fluorinated cycloalkyl group, a phenyl group, or a fluorinated phenyl group;
L4 are each independently absent or present and when present are each independently an alkyl group, a fluorinated alkyl group, a branched alkyl group;
R1 are each independently absent or present and when present are each independently an ether, a thioether, an ester, an amide, a carbamic acid derivative, urea, a secondary amine, or a tertiary amine;
R2 are each independently absent or present and when present are each independently an ether, a thioether, an ester, an amide, a carbamic acid derivative, urea, a secondary amine, or a tertiary amine; and
n>1.

### Claim 2 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein A is a boron atom, an aluminum atom, a carbon atom, or a silicon atom.

### Claim 3 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein A is:

### Claim 4 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1,
wherein n is 2, 3 or 5.

### Claim 5 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein L is an alkyl group.

### Claim 6 (depends on 5)

The multifunctionalized thiol conductor compound of claim 5, wherein L is —CH2CH3.

### Claim 7 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein Rf is CF3.

### Claim 8 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein the electron-withdrawing group is —CN, —NO2, —CF3, or —SO2CF3.

### Claim 9 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein the monovalent cation is an alkali metal cation.

### Claim 10 (depends on 9)

The multifunctionalized thiol conductor compound of claim 9, wherein the alkali metal cation is H+, K+, Na+, Li+, Rb+, or Cs+.

### Claim 11 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein L1 are an alkyl group is a n alkyl group and n is 1, 2, 3, 4, 5 or 6.

### Claim 12 (depends on 11)

The multifunctionalized thiol conductor compound of claim 11, wherein L1 are —CH2—.

### Claim 13 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein R1 are an ester.

### Claim 14 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein L3 are an alkyl group.

### Claim 15 (depends on 14)

The multifunctionalized thiol conductor compound of claim 14, wherein L3 are (CH2)2.

### Claim 16 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, wherein R2 are an ester.

### Claim 17 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, having formula II:
wherein A is a boron atom, an aluminum atom,
L is absent.

### Claim 18 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, having formula II:
wherein A is a carbon atom or a silicon atom; and
L is present.

### Claim 19 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, having formula III:
wherein A is a carbon atom or a silicon atom; and
L is absent.

### Claim 20 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, having formula IV:
wherein A is a dipentaerythritol core
L is absent; and
n=5.

### Claim 21 (depends on 1)

The multifunctionalized thiol conductor compound of claim 1, having formula V or formula VI:
wherein R is

### Claim 22 (depends on 1)

A method for the synthesis of the multifunctionalized thiol conductor compound of claim 1, the method comprising reacting a multifunctional thiol compound with a lithium bis(trifluoromethanesulfonyl)imide (LiTFSI)-monomer having a C═C in its backbone.

### Claim 23 (depends on 1)

A single-ion conducting polymer electrolyte comprising the multifunctionalized thiol conductor compound as defined in claim 1.