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US 10,995,217 B2Granted
Compounds as potential dye molecules
AssigneeLleaf Pty Ltd
InventorAlexander Falber
Life of this patent
Estimating the term…
Abstract
Disclosed herein are a series of compounds based on Formula (I). These compounds comprise perylene core which has been extended with optionally functionalised imidazoles at the 3,4;9,10 positions. The compounds of Formula (I) can be functionalised at two positions on the perylene core, such as the 1,6 or 1,7 positions. Also disclosed herein are compositions comprising said compounds, methods of forming said compounds and potential applications of said compounds, such as applying the compounds as a dye whose absorbance and fluorescence spectrum are red-shifted.
Claims20
A compound of Formula (I):
- or a salt thereof, wherein:
- for R1, R2 and R3 either:
- (i) R1 is O, R3 is N, and R2 and R3 are joined by a
- group;
- or
- (ii) R3 is O, R1 is N, and R1 and R2 are joined by a
- group;
- for R4, R5 and R6 either:
- (i) R4 is O, R6 is N, and R5 and R6 are joined by a
- group;
- or
- (ii) R6 is O, R4 is N, and R4 and R5 are joined by a
- group;
- R10 and R11 are joined to form:
- an optionally substituted monocyclic aromatic ring;
- or an optionally substituted polycyclic aromatic group;
- R12 and R13 are joined to form:
- an optionally substituted monocyclic aromatic ring;
- or an optionally substituted polycyclic aromatic group;
- each of R7, R8 and R9 is
- independently selected from hydrogen or
- with the proviso that two of R7, R8 and R9 are
- and the other is hydrogen
- each R14 is independently selected from:
- alkyl, alkenyl, alkynyl, halogen, nitro, cyano, hydroxy, sulfonic, thiol, ether, amino, alkylamino, dialkylamino, haloalkyl, hydroxyalkyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy, aralkyloxy, alkylthio, carboxamido, sulfonamido, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, carboxy, carboxyalkyl, cycloalkyl, aryl, heteroaryl, heterocyclo, alkoxyalkyl, (amino)alkyl, hydroxyalkylamino, (alkylamino)alkyl, (dialkylamino)alkyl, (cyano)alkyl, (carboxamido)alkyl, mercaptoalkyl, (heterocyclo)alkyl, (cycloalkylamino)alkyl, (C1-C4 haloalkoxy)alkyl, (heteroaryl)alkyl, or perylene groups, each of which optionally comprises one or more substituents;
- represents the presence of a single or double bond;
- and
- n is an integer selected from 0, 1, 2, 3, 4 or 5,
- wherein when:
- a) R1 is O, R3 is N, and R2 and R3 are joined by a
- group;
- and R4 is O, R6 is N, and R5 and R6 are joined by a
- group;
- or
- b) R3 is O, R1 is N, and R1 and R2 are joined by a
- group;
- and R6 is O, R4 is N, and R4 and R5 are joined by a
- group,
- then R8 is H and R7 and R9 are
36 more elements
A dye composition comprising a compound of Formula (I):
- or a salt thereof, wherein:
- for R1, R2 and R3 either:
- (i) R1 is O, R3 is N, and R2 and R3 are joined by a
- group;
- or
- (ii) R3 is O, R1 is N, and R1 and R2 are joined by a
- group;
- for R4, R5 and R6 either:
- (i) R4 is O, R6 is N, and R5 and R6 are joined by a
- group;
- or
- (ii) R6 is O, R4 is N, and R4 and R5 are joined by a
- group;
- R10 and R11 are joined to form:
- an optionally substituted monocyclic aromatic ring;
- or an optionally substituted polycyclic aromatic group;
- R12 and R13 are joined to form:
- an optionally substituted monocyclic aromatic ring;
- or an optionally substituted polycyclic aromatic group;
- each of R7, R8 and R9 is
- independently selected from hydrogen or
- with the proviso that two of R7, R8 and R9 are
- and the other is hydrogen;
- each R14 is independently selected from:
- alkyl, alkenyl, alkynyl, halogen, nitro, cyano, hydroxy, sulfonic, thiol, ether, amino, alkylamino, dialkylamino, haloalkyl, hydroxyalkyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy, aralkyloxy, alkylthio, carboxamido, sulfonamido, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, carboxy, carboxyalkyl, cycloalkyl, aryl, heteroaryl, heterocyclo, alkoxyalkyl, (amino)alkyl, hydroxyalkylamino, (alkylamino)alkyl, (dialkylamino)alkyl, (cyano)alkyl, (carboxamido)alkyl, mercaptoalkyl, (heterocyclo)alkyl, (cycloalkylamino)alkyl, (C1-C4 haloalkoxy)alkyl, (heteroaryl)alkyl, or perylene groups, each of which optionally comprises one or more substituents;
- represents the presence of a single or double bond;
- and
- n is an integer selected from 0, 1, 2, 3, 4 or 5;
- wherein when:
- a) R1 is O, R3 is N, and R2 and R3 are joined by a
- group;
- and R4 is O, R6 is N, and R5 and R6 are joined by a
- group;
- or
- b) R3 is O, R1 is N, and R1 and R2 are joined by a
- group;
- and R6 is O, R4 is N, and R4 and R5 are joined by a
- group,
- then R8 is H and R7 and R9 are
36 more elements
A method of synthesizing a compound of Formula (I):
- or a salt thereof, wherein:
- for R1, R2 and R3 either:
- (i) R1 is O, R3 is N, and R2 and R3 are joined by a
- group;
- or
- (ii) R3 is O, R1 is N, and R1 and R2 are joined by a
- group;
- for R4, R5 and R6 either:
- (i) R4 is O, R6 is N, and R5 and R6 are joined by a
- group;
- or
- (ii) R6 is O, R4 is N, and R4 and R5 are joined by a
- group;
- R10 and R11 are joined to form:
- an optionally substituted monocyclic aromatic ring;
- or an optionally substituted polycyclic aromatic group;
- R12 and R13 are joined to form:
- an optionally substituted monocyclic aromatic ring;
- or an optionally substituted polycyclic aromatic group;
- each of R7, R8 and R9 is
- independently selected from hydrogen or
- with the proviso that two of R7, R8 and R9 are
- and the other is hydrogen;
- each R14 is independently selected from:
- alkyl, alkenyl, alkynyl, halogen, nitro, cyano, hydroxy, sulfonic, thiol, ether, amino, alkylamino, dialkylamino, haloalkyl, hydroxyalkyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy, aralkyloxy, alkylthio, carboxamido, sulfonamido, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, carboxy, carboxyalkyl, cycloalkyl, aryl, heteroaryl, heterocyclo, alkoxyalkyl, (amino)alkyl, hydroxyalkylamino, (alkylamino)alkyl, (dialkylamino)alkyl, (cyano)alkyl, (carboxamido)alkyl, mercaptoalkyl, (heterocyclo)alkyl, (cycloalkylamino)alkyl, (C1-C4 haloalkoxy)alkyl, (heteroaryl)alkyl, or perylene groups, each of which optionally comprises one or more substituents;
- represents the presence of a single or double bond;
- and
- n is an integer selected from 0, 1, 2, 3, 4 or 5,
- wherein when:
- a) R1 is O, R3 is N, and R2 and R3 are joined by a
- group;
- and R4 is O, R6 is N, and R5 and R6 are joined by a
- group;
- or
- b) R3 is O, R1 is N, and R1 and R2 are joined by a
- group;
- and R6 is O, R4 is N, and R4 and R5 are joined by a
- group,
- then R8 is H and R7 and R9 are
- the method comprising the step of contacting a compound of Formula (II):
- wherein each of R15, R16 and R17 is independently selected from hydrogen, bromine or chlorine, with the proviso that two of R15, R16 and R17 are either bromine or chlorine, and the other is hydrogen, with a compound of Formula (III):
- wherein R19 and R20:
- are joined to form an optionally substituted monocyclic aromatic ring;
- or are joined to form an optionally substituted polycyclic aromatic group.
41 more elements
Dependencies are inferred from the claim text.