# US 2014/0154815 A1 · Luminescent Compounds, Complexes and Their Uses

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0154815 A1
- Document ID: US20140154815A1
- Status: Published application
- Kind: A1
- Application number: 14/111,610
- Filed: 2012-04-13
- Published: 2014-06-05
- Earliest claimed: 2011-04-15
- Assignees: London Metropolitan University
- Inventors: Sim-Wan Annie Bligh; Nicholas Paul Chatterton; Nicholas James Wardle; Jason Lee Sarris; Gaoyun Chen
- Web page: https://patentgrep.com/patent/US20140154815A1

## CPC

- G01N 21/77: by observing the effect on a chemical indicator
- C07D 403/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 403/14: containing three or more hetero rings
- C07F 5/00: Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C09K 9/02: Organic tenebrescent materials
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/182: of the rare earth metals, i.e. Sc, Y or lanthanide
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A method of changing the fluorescent properties of a complex, the method comprising: providing a first complex comprising a multidentate ligand that is coordinated to a lanthanide ion, wherein the lanthanide is selected from europium and terbium and the multidentate ligand has at least one optionally substituted phthalimide group coordinated to the lanthanide ion, contacting the complex with an aqueous liquid medium under appropriate conditions, such that at least one phthalimide group is hydrolysed to a phthalamate group, to form a second complex. Complexes and compounds are also disclosed.

## Claims

### Claim at position 1

1-20. (canceled)

### Claim 21

A complex comprising:
a multidentate ligand that is coordinated to a lanthanide ion, wherein
the lanthanide is selected from europium and terbium, and
the multidentate ligand has (i) at least one optionally substituted phthalimide group coordinated to the lanthanide ion or (ii) at least one optionally substituted phthalamate group coordinated to the lanthanide ion.

### Claim 22 (depends on 21)

A complex according to claim 21, the complex comprising
the lanthanide ion and the multidentate ligand, wherein the ligand is of formula (I)
L1, L2, L3, L4 are each selected from —(CR5R5)n—, wherein n is 2 or 3,
R1, R2, R3 and R4 are each independently selected from L5-X1 and L6-X2,
L5 and L6 are each independently an organic linker group,
X1 is an optionally substituted phthalimide group or optionally substituted phthalamate group, and
X2 is a group that binds to the lanthanide ion other than a substituted phthalimide group and a optionally substituted phthalamate group,
wherein each R5 is independently selected from H and an optionally substituted hydrocarbon group,
and at least one of R1, R2, R3 and R4 is L5-X1.

### Claim 23 (depends on 22)

The complex according to claim 22, wherein X1 is an optionally substituted phthalimide group.

### Claim 24 (depends on 22)

The complex according to claim 22, wherein X1 is an optionally substituted phthalamate group.

### Claim 25 (depends on 22)

The complex according to claim 22, wherein at least two of R1, R2, R3 and R4 is L5-X1.

### Claim 26 (depends on 22)

The complex according to claim 22, wherein L1, L2, L3, L4 are each selected from —(CR5R5)n—, wherein each R5 is H and n is 2.

### Claim 27 (depends on 22)

The complex according to claim 22, wherein in each L5-X1, L5 is an optionally substituted alkylene having from 1 to 10 carbons atoms, excluding any substituents that may be present.

### Claim 28 (depends on 22)

The complex according to claim 22, wherein in each L5-X1, L5 is a linker group of the formula —(CH2)q—, wherein q is 1 to 5.

### Claim 29 (depends on 22)

The complex according claim 22, wherein in each L6-X2, L6 is an optionally substituted alkylene having from 1 to 10 carbons atoms, excluding any substituents that may be present.

### Claim 30 (depends on 22)

The complex according to claim 22, wherein in each L6-X2, L6 is a linker group of the formula —(CH2)q—, wherein q is 1 to 5.

### Claim 31 (depends on 22)

The complex according to claim 22, wherein X2 is selected from —CO2, —CO2R6, —O, OR6, —NHR6, —C(═O)R6, —C(═O)N(R6)2, —PO(O)2, —PO(O)(OR6), —PO(OR6)2, —SR6, —SOR6, —SO2, —SO2R6, —NHC(═O)R6, —NHC(═O)NHR6, —NHC(═S)NHR6, and Q
wherein each R6 is independently selected from H and an optionally substituted hydrocarbon group,
Q is a group selected from
wherein R10 and R11 are independently selected at each occurrence from: H and an optionally substituted hydrocarbon group;
m is 1-3;
W is two hydrogen atoms;
X is selected from O or NR7; wherein R7 is selected from H and optionally substituted hydrocarbon, and
Z1, Z2 and Z3 are independently selected from: O, NH, CH2NH, and a direct bond.

### Claim 32 (depends on 31)

The complex according to claim 31, wherein X2 is —CO2.

### Claim 33

A method of changing the fluorescent properties of a complex, the method comprising:
providing a first complex comprising a multidentate ligand that is coordinated to a lanthanide ion,
wherein the lanthanide is selected from europium and terbium and the multidentate ligand has at least one optionally substituted phthalimide group coordinated to the lanthanide ion,
contacting the complex with an aqueous liquid medium under appropriate conditions, such that at least one phthalimide group is hydrolyzed to a phthalamate group, to form a second complex.

### Claim 34 (depends on 33)

The method according to claim 33, wherein the first complex comprises a lanthanide ion and a multidentate ligand, wherein the ligand is of formula (I)
L1, L2, L3, L4 are each selected from —(CR5R5)n—, wherein n is 2 or 3,
R1, R2, R3 and R4 are each independently selected from L5-X1 and L6-X2,
L5 and L6 are each independently an organic linker group,
X1 is an optionally substituted phthalimide group, and
X2 is a group that binds to the lanthanide ion other than an optionally substituted phthalimide group and a optionally substituted phthalamate group,
wherein each R5 is independently selected from H and an optionally substituted hydrocarbon group,
and at least one of R1, R2, R3 and R4 is L5-X1.

### Claim 35

Use of a complex for detecting a change in pH, wherein the complex comprises a multidentate ligand that is coordinated to a lanthanide ion, wherein the lanthanide is selected from europium and terbium and the multidentate ligand has (i) at least one optionally substituted phthalimide group coordinated to the lanthanide ion or (ii) at least one optionally substituted phthalamate group coordinated to the lanthanide ion.

### Claim 36 (depends on 35)

The use according to claim 35, the complex comprising the lanthanide ion and the multidentate ligand, wherein the ligand is of formula (I)
L1, L2, L3, L4 are each selected from —(CR5R5)n—, wherein n is 2 or 3,
R1, R2, R3 and R4 are each independently selected from L5-X1 and L6-X2,
L5 and L6 are each independently an organic linker group,
X1 is an optionally substituted phthalimide group or optionally substituted phthalamate group, and
X2 is a group that binds to the lanthanide ion other than a substituted phthalimide group and a optionally substituted phthalamate group,
wherein each R5 is independently selected from H and an optionally substituted hydrocarbon group,
and at least one of R1, R2, R3 and R4 is L5-X1.

### Claim 37 (depends on 36)

The use according to claim 36, wherein X1 is an optionally substituted phthalimide group.

### Claim 38 (depends on 36)

The use according to claim 36, wherein X1 is an optionally substituted phthalamate group

### Claim 39 (depends on 36)

The use according to claim 36, wherein at least two of R1, R2, R3 and R4 is L5-X1.

### Claim 40 (depends on 36)

The use according to claim 36, wherein X2 is —CO2.