Compounds as potential dye molecules
AssigneeLleaf Pty Ltd
InventorAlexander FALBER
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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.
Claims29
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 either:
- independently selected from hydrogen or
- with the proviso that two of R7, R8 and R9 are
- and the other is hydrogen;
- or
- independently selected from hydrogen, bromine or chlorine, with the proviso that two of R7, R8 and R9 are either bromine or chlorine, 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.
The compound according to any one of the preceding claims, wherein R7 and R9 are
- and R8 is hydrogen.
The compound according to any one of the preceding claims, wherein R8 and R9 are
- and R7 is hydrogen.
The compound according to any one of the preceding claims, wherein the optionally substituted monocyclic aromatic ring or optionally substituted polycyclic aromatic group formed by R10 and R11 is the same as the optionally substituted monocyclic aromatic ring or optionally substituted polycyclic aromatic group formed by R12 and R13.
The compound according to any one of the preceding claims, wherein the optionally substituted monocyclic aromatic ring or optionally substituted polycyclic aromatic group is selected from the group consisting of optionally substituted:
- phenyl, naphthalene, anthracene, phenanthrene, tetracene, chrysene, triphenylene, pyrene, pentacene, benzo[a]pyrene, and dibenz[a,h]anthracene groups.
The compound according to any one of the preceding claims, wherein the optionally substituted monocyclic aromatic ring or optionally substituted polycyclic aromatic group is selected from the group consisting of optionally substituted:
The compound according to any one of the preceding claims, wherein the optionally substituted monocyclic aromatic ring is:
The compound according to any one of the preceding claims, wherein R14 is an optionally substituted alkyl group.
The compound according to any one of the preceding claims, wherein R14 is an optionally substituted perylene.
The compound according to any one of the preceding claims, wherein n is 0.
The compound according to any one of the preceding claims, wherein
- is selected from the group consisting of optionally substituted:
- or a mixture thereof.
The compound according to any one of the preceding claims, wherein the compound has an absorbance in a range of about 600 nm to about 800 nm in a UV/Vis spectrum.
The compound according to any one of the preceding claims, wherein the compound is has a fluorescence maxima in a range of about 625 nm to about 900 nm.
A dye composition comprising a compound according to any one of the preceding claims.
Dependencies are inferred from the claim text.