LUMINESCENT COMPOUNDS

Abstract

sents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and/or an aliphatic group; p is an integer of 1 or 2; q and s are independently integers of 1, 2, 3, or 4; Y.sup.1, Y.sup.2, and Y.sup.3 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, an oxygen atom, a nitrogen atom, a cyano group, or a nitro group; two or more of Y.sup.1, Y.sup.2, and/or Y.sup.3 may combine together to form a condensed ring; wherein one or more of Y.sup.1, Y.sup.2, and/or Y.sup.3 comprises a spacing portion comprising a continuous chain of between 3 and 20 atoms, and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl, and/or an aliphatic alcohol.

##STR00001##

Claims

1.-25. (canceled)

26. A luminescent compound represented by the following general formula: ##STR00029## wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and/or an aliphatic group; p is an integer of 1 or 2; q and s are independently integers of 1, 2, 3, or 4; Y.sup.1, Y.sup.2, and Y.sup.3 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, an oxygen atom, a nitrogen atom, a cyano group, or a nitro group; two or more of Y.sup.1, Y.sup.2, and/or Y.sup.3 may combine together to form a condensed ring; wherein one or more of Y.sup.1, Y.sup.2, and/or Y.sup.3 comprises a spacing portion comprising a continuous chain of between 3 and 20 atoms, and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl, and/or an aliphatic alcohol.

27. A luminescent compound according to claim 26, represented by the following general formula: ##STR00030## wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and/or an aliphatic group; Y.sup.4, Y.sup.5, Y.sup.6, Y.sup.7, Y.sup.8, Y.sup.9, Y.sup.10, Y.sup.11, Y.sup.12, Y.sup.13 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, an oxygen atom, a nitrogen atom, a cyano group, a nitro group; two or more of Y.sup.4, Y.sup.5, Y.sup.6, Y.sup.7, Y.sup.8, Y.sup.9, Y.sup.10, Y.sup.11, Y.sup.12, Y.sup.13 may combine together to form a condensed ring; wherein one or more of Y.sup.4, Y.sup.5, Y.sup.6, Y.sup.7, Y.sup.8, Y.sup.9, Y.sup.10, Y.sup.11, Y.sup.12, Y.sup.13comprises a spacing portion comprising a continuous chain of between 3 and 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl, and/or an aliphatic alcohol.

28. A luminescent compound according to claim 26, wherein the functional group capable of forming a covalent bond with a second species is located at a or the terminus of the spacing portion.

29. A luminescent compound according to claim 26, wherein the spacing portion comprises a continuous chain of between 3 and 20 atoms selected from carbon atoms or a combination of carbon atoms and heteroatoms.

30. A luminescent compound according to claim 29, wherein the spacing portion comprises or consists of a polyether chain comprising a continuous chain of between five and twenty atoms selected from carbon atoms and oxygen atoms.

31. A luminescent compound according to claim 30, wherein the spacing portion and the functional group (FG) capable of forming a covalent bond with a second species consists of a —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2CH.sub.2-FG moiety or a —(CH.sub.2CH.sub.2O).sub.2CH.sub.2FG moiety, such that one or more of Y.sup.1 to Y.sup.3 consists of an —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2CH.sub.2FG moiety or an —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2FG moiety.

32. A luminescent compound according to claim 26, wherein one or more of Y.sup.1 to Y.sup.3 independently represent an alkoxy group and/or wherein R represents an aromatic group, a substituted phenyl group or a polycyclic aromatic hydrocarbon.

33. A luminescent compound according to claim 26, comprising a single spacing portion and a single functional group capable of forming a covalent bond with a second species.

34. A luminescent compound according to claim 27, wherein Y.sup.5, Y.sup.6, Y.sup.9, Y.sup.10, Y.sup.13 each represent a hydrogen atom, Y.sup.4, Y.sup.7, Y.sup.8 Y.sup.11 each represent an OR′ group, and Y.sup.12 represents a —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2CH.sub.2FG moiety.

35. A luminescent compound according to claim 26, represented by the following general formula: ##STR00031## wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom; R independently represents an aromatic group and/or an aliphatic group; q is independently an integer of 1 to 3; s is independently an integer of 1 to 4; t is independently an integer of 1 to 4; Y.sup.2, Y.sup.3, and Y.sup.14 and J independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, an oxygen atom, a nitrogen atom, a cyano group, a nitro group; two or more of Y.sup.2, Y.sup.3, and/or Y.sup.14 may combine together to form a condensed ring; wherein one or more of Y.sup.2, Y.sup.3, Y.sup.14 and/or J comprise a spacing portion comprising a continuous chain of between 3 and 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate a carbonyl, and/or an aliphatic alcohol.

36. A luminescent compound according to claim 35, wherein the spacing portion of one or more of Y.sup.2, Y.sup.3, and/or Y.sup.14 comprises a polyether chain, which is covalently bonded to the functional group capable of forming a covalent bond with a second species, e.g. the spacing portion consists of an —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2CH.sub.2—moiety or a —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2— moiety.

37. A luminescent compound according to claim 35, represented by the following general formula: ##STR00032## wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom; R independently represents an aromatic group and/or an aliphatic group; Y.sup.15, Y.sup.16, Y.sup.17, Y.sup.18, Y.sup.19, Y.sup.20, Y.sup.21, Y.sup.22, Y.sup.23, Y.sup.24, Y.sup.25, Y.sup.26, independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, an oxygen atom, a nitrogen atom, a cyano group, a nitro group; two or more of Y.sup.15, Y.sup.16, Y.sup.17, Y.sup.18, Y.sup.19, Y.sup.20, Y.sup.21, Y.sup.22, Y.sup.23, Y.sup.24, Y.sup.25, Y.sup.26 combine together to form a condensed ring; wherein one or more of Y.sup.15, Y.sup.17, Y.sup.18, Y.sup.20, Y.sup.21, Y.sup.24, Y.sup.25 comprises a spacing portion comprising a continuous chain of between 3 and 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate a carbonyl, and/or an aliphatic alcohol.

38. A luminescent compound represented by the following general formula: ##STR00033## wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and/or an aliphatic group; J.sup.1, J.sup.2, J.sup.3, J.sup.4, J.sup.5 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, an oxygen atom, a nitrogen atom, a cyano group, a nitro group; wherein J.sup.1 and J.sup.2, or J.sup.3 and J.sup.4 may combine together to form a condensed ring; A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 independently represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, a polyether group; wherein one or more of A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 comprises a functional group capable of forming a covalent bond with a second species.

39. A luminescent compound according to claim 37, wherein the functional group is selected from a carboxylic acid moiety, an ester, an azide, an amine, a maleimide, a thiol moiety, an isothiocyanate a carbonyl and/or an aliphatic alcohol and/or wherein four out of five of A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 independently represent an alkyl group and/or wherein one out of five of A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 comprises or consists of a spacing portion and a functional group capable of forming a covalent bond with a second species.

40. A luminescent compound according to claim 38, wherein the functional group (FG) is provided at a terminus of the spacing portion, and the spacing portion and functional group are selected from —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2CH.sub.2FG or —O—(CH.sub.2CH.sub.2O).sub.2CH.sub.2FG.

41. A luminescent compound according to claim 39, wherein X represents an oxygen atom and J.sup.1, J.sup.2, J.sup.3, J.sup.4, J.sup.5 independently represent a hydrogen atom.

42. A luminescent compound according to claim 26, covalently bonded to a second species.

43. A kit of parts suitable for use in covalently bonding the luminescent compound of claim 26 to a second species, the kit of parts comprising one or more luminescent compound(s) of claim 26 and a solvent suitable for dissolving or suspending the luminescent compound(s).

44. A luminescent compound according to claim 38, covalently bonded to a second species.

45. A kit of parts suitable for use in covalently bonding the luminescent compound of claim 38 to a second species, the kit of parts comprising one or more luminescent compound(s) of claim 38 and a solvent suitable for dissolving or suspending the luminescent compound(s).

Description

[0253] To further exemplify the invention, reference is also made to the following non-limiting Examples, in which reference to the accompanying drawings:

[0254] FIG. 1 is a table illustrating the structures of the luminescent compounds according to Examples of the invention;

[0255] FIG. 2 is a synthetic route to the precursors used to produce compounds according to Examples of the invention;

[0256] FIG. 3 is an absorption and emission spectra of Compound 39;

[0257] FIG. 4 is a schematic route to conjugate an antibody to a luminescent compound according to an embodiment of the invention;

[0258] FIG. 5 is a series of spectra showing the conjugation of an antibody to a luminescent compound, according to an Example of the invention;

[0259] FIG. 6 is a series of images showing the conjugation of an antibody to a luminescent compound, according to an Example of the invention; and

[0260] FIG. 7 is Compound 44 according to a further Example of the invention.

[0261] Referring now to FIG. 2, there is shown a synthetic route to the precursors used to produce the compounds according to Examples of the invention. Compounds 38 to 43 were synthesised from Precursor 8, which in turn was synthesised from Compound 3, which in turn was synthesised from Precursor 2.

[0262] Precursor 2 was fabricated according to the method described in N. Boden et. al. J. Mater. Chem., 1995, 5, 2275.

Synthesis of Compound 3

[0263] Compound 3 was synthesised using the following method. A solution of 2-naphthalene carboxylic acid (225 mg, 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in PhMe (5 mL) was heated at 70° C. under N.sub.2 for 20 min. A solution of Precursor 2 (100 mg; 0.131 mmol) in PhMe (2 mL) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH.sub.2Cl.sub.2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2×20 mL), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40% CH.sub.2Cl.sub.2: 60% n-hexane) to afford Compound 3 as a yellow solid (35 mg; 32%).

[0264] The name for Compound 3 is 8-(naphthalen-2-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d]oxazole.

[0265] Compound 3 had the following characterisation data: .sup.1H NMR (300 MHz, CDCl.sub.3) δH: 10.22 (1 H, s), 8.89 (1 H, s), 8.49 (1 H, dd, J 8.6, 1.7), 8.05-7.99 (2 H, m), 7.96-7.91 (5 H, m), 7.62-7.59 (2 H, m), 4.54 (2 H, t, J 6.8), 4.51 (2 H, t, J 6.8), 4.32-4.25 (6 H, m), 2.17-1.93 (10 H, m), 1.76-1.42 (20 H, m), 1.06-0.97 (15 H, m) ppm. .sup.13C NMR (100 MHz, CDCl.sub.3) 6C: 161.7, 149.8, 149.3, 149.0, 148.6, 143.2, 140.9, 140.6, 135.0, 133.4, 129.3, 128.9, 128.3, 128.0, 127.9, 127.4, 127.2, 125.0, 125.0, 124.4, 124.2, 123.7, 123.6, 116.7, 111.2, 108.5, 107.1, 107.0, 103.9, 70.2, 70.1, 69.8, 69.2, 29.6, 29.5, 28.9, 28.8, 28.7, 23.1, 23.0, 14.6, 14.5 ppm. MALDI+m/z: 825.5 ([M]+100%). IR λ-1 (neat): Elemental analysis Found: C, 78.95; H, 8.02; N, 1.83%. C.sub.54H.sub.67NO.sub.6 requires C, 78.51; H, 8.17; N, 1.70 %.

Synthesis of Precursor 8

[0266] Precursor 8 was synthesised using the following method. 8-(Naphthalen-2-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d]oxazole (Compound 3) (150 mg, 0.18 mmol, 1 eq) was dissolved in CH.sub.2Cl.sub.2 (10 mL) which had been dried and degassed for 10 min in a 2 necked flask fitted with a subaseal and had been purged with N.sub.2 for 10 min. The green solution was stirred at −10° C. under N.sub.2 for 10 min and boron tribromide (1M in CH.sub.2Cl.sub.2 solution) (0.2 mmol, 1.1 eq) was added via syringe through the subaseal. The black solution was stirred under N.sub.2 for 2 h at −10° C. and then poured over crushed ice and stirred until all the ice had melted. The product was then extracted with ethyl acetate (20 mL), washed with water (3×50 mL) and evaporated to dryness yielding a brown solid. The product was then purified by flash column chromatography (20% EtOAc: n-hexane, silica) yielding 8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-ol as a yellow solid (31 mg, 23%).

[0267] The name for Precursor 8 is 8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-ol.

[0268] Precursor 8 had the following characterisation data .sup.1H NMR δ.sub.H: (300 MHz, CDCl.sub.3) 10.06 (1H, s), 8.83 (1H, s), 8.50 (1H, dd, J 8.6, 1.7), 8.05-8.03 (1H, m), 7.79 (1H, d, J 8.7), 7.91-7.89 (1H, m), 7.84 (1H, s), 7.79 (1H, s), 7.78 (1H, s), 7.74 (1H, s), 7.58-7.56 (2H, m), 5.97 (1H, s), 4.42 (2H, t, J 6.7), 4.29-4.20 (6H, m), 2.05-1.93 (8H, m), 1.63-1.45 (16H, m), 1.05-0.98 (12H, m) ppm. .sup.13C NMR δc: (100 MHz, CDCl.sub.3) 161.7, 149.4, 148.9, 146.0, 145.3, 143.0, 140.9, 140.2, 134.8, 133.2, 129.1, 128.66, 128.0, 127.9, 127.6, 127.2, 126.8, 124.8, 124.7, 124.7, 124.0, 123.6, 123.4, 116.4, 112.7, 108.1, 107.1, 103.7, 103.6, 69.9, 69.8, 69.7, 69.1, 29.3, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8, 22.7, 14.3, 14.2 ppm. MALDI m/z: 755.65 ([M].sup.30 100%), 756.66 ([M+H].sup.+ 70%), 757.67 ([M+1+H].sup.+ 25%).

EXAMPLE 1—SYNTHESIS OF COMPOUND 38

[0269] Compound 38 was synthesised by the following method. A slurry of Precursor 8 (100 mg, 0.13 mmol) and K.sub.2CO.sub.3 (114 mg, 0.83 mmol) in DMF (5 mL) was heated at reflux with a CaCl.sub.2 drying tube for 0.5 h, followed by addition of methyl 2-(2-(2-chloroethoxy)ethoxy)acetate (114 mg, 0.40 mmol) and KI (75 mg, 0.5 mmol). The resultant slurry was further heated at reflux for 3 h. The reaction mixture was allowed to cool to room temperature and the precipitate filtered off via suction filtration. The solvent was evaporated from the filtrate to dryness in vacuo and the crude solid was purified by purified via flash column chromatography (silica, 25% EtOAc: 75% n- hexane) to afford Compound 38 as a yellow solid (36 mg, 30%).

[0270] The name for Compound 38 is methyl 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetate.

[0271] Compound 38 had the following characterisation data: .sup.1H NMR δ.sub.H: (300 MHz, CDCl.sub.3) 10.16 (1H, s), 8.83 (1H, s), 8.50 (1H, dd, J 8.6, 1.7), 8.05-8.03 (2H, m), 7.91-7.81 (5H, m), 7.58-7.56 (2H, m), 4.60 (2H, t, J 5.5), 4.42 (2H, t, J 6.7), 4.29-4.21 (6H, m), 4.20 (3H, s), 3.85-3.65 (8H, m), 2.05-1.93 (8H, m), 1.63-1.45 (16H, m), 1.05-0.98 (12H, m) ppm. .sup.13C NMR δc: (100 MHz, CDCl.sub.3) 173.9, 161.7, 149.4, 148.9, 145.9, 145.3, 142.0, 140.8, 140.4, 134.8, 133.1, 129.1, 128.7, 128.0, 127.9, 127.6, 127.2, 126.8, 124.8, 124.7, 124.6, 124.0, 123.6, 123.3, 116.5, 112.7, 108.1, 107.1, 103.7, 103.6, 71.8, 71.4, 71.2, 70.4, 69.8, 69.8, 69.7, 69.0, 68.5, 29.4, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8, 22.7, 14.3, 14.2 ppm. MALDI m/z: 915.7 ([M].sup.+ 100%), 916.7 ([M+H].sup.+ 90%). Elemental analysis Found: C, 73.41; H, 7.56; N, 1.54%. C.sub.58H.sub.69NO.sub.10 requires C, 73.42; H, 7.59; N, 1.53%.

EXAMPLE 2—SYNTHESIS OF COMPOUND 39

[0272] Compound 39 was synthesised using the following method. A solution of NaOH (3 mg, 0.08 mmol) in H.sub.2O (1 mL) was added to a solution of Compound 38 (35 mg, 0.04 mmol in MeOH (5 mL). The resultant solution was heated at reflux for 5 h. The reaction mixture was allowed to cool to room temperature and aliquots of 1M HCl aqueous solution was added until no further precipitate was formed. The precipitate was collected through suction filtration affording a yellow solid (24 mg, 70%).

[0273] The name for Compound 39 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetic acid.

[0274] Compound 39 had the following characterisation data: .sup.1H NMR δH: (300 MHz, CDCl.sub.3) 10.16 (1H, s), 8.83 (1H, s), 8.50 (1H, dd, J 8.6, 1.6), 8.05-8.03 (2H, m), 7.91-7.81 (5H, m), 7.58-7.56 (2H, m), 4.60 (2H, t, J 5.5 Hz), 4.42 (2H, t, J 6.7 Hz), 4.29-4.21 (6H, m), 3.85-3.65 (8H, m), 2.05-1.93 (8H, m), 1.63-1.45 (16H, m), 1.05-0.98 (12H, m) ppm. .sup.13NMR δc: (100 MHz, CDCl3) 175.7, 149.4, 148.9, 145.9, 145.3, 142.0, 140.8, 140.4, 134.8, 133.1, 129.1, 128.7, 128.0, 127.9, 127.6, 127.2, 126.8, 124.8, 124.7, 124.6, 124.0, 123.6, 123.3, 116.5, 112.7, 108.1, 107.1, 103.7, 103.6, 71.8, 71.4, 71.2, 70.4, 69.8, 69.8, 69.7, 69.0, 68.5, 29.4, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8, 22.7, 14.3, 14.2 ppm. MALDI m/z: 901.5 ([M].sup.+ 100%), 902.5 ([M+H].sup.+ 70%). Elemental analysis Found: C, 73.24; H, 7.52; N, 1.54%. C.sub.55H.sub.67NO.sub.10 requires C, 73.23; H, 7.55; N, 1.55%.

[0275] Referring now to FIG. 3, there is shown a spectra 30. There is shown the absorption spectra 31 and emission spectra 32 for Compound 39 in ethyl acetate.

EXAMPLE 3—SYNTHESIS OF COMPOUND 40

[0276] Compound 40 was synthesised using the following method. A slurry of Precursor 8 (100 mg, 0.13 mmol) and K.sub.2CO.sub.3 (37 mg, 0.26 mmol) in MeCN (5 mL) was heated at reflux with a CaCl.sub.2 drying tube for 0.5 h, followed by addition of 2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (87 mg, 0.26 mmol). The resultant slurry was further heated at reflux for 24 h. The reaction mixture was allowed to cool to room temperature and the precipitate filtered off via suction filtration. The solvent was evaporated from the filtrate to dryness in vacuo and the crude solid was purified by purified via flash column chromatography (silica, 25% EtOAc: 75% n- hexane) to afford Compound 38 as a yellow solid (18 mg, 15%).

[0277] The name for Compound 40 is 11-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)-8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazole.

[0278] Compound 40 had the following characterisation data: .sup.1H NMR δ.sub.H: (300 MHz, CDCl.sub.3) 10.14 (1H, s), 8.82 (1H, s), 8.51 (1H, dd, J 8.6, 1.7), 8.06-8.03 (2H, m), 7.91-7.80 (5H, m), 7.57-7.55 (2H, m), 4.59 (2H, t, J 5.5 Hz), 4.41 (2H, t, J 6.7 Hz), 4.29-4.20 (6H, m), 4.15-4.10 (2H, m), 3.87-3.82 (2H, m), 3.69-3.57 (4H, m), 3.30-3.21 (2H, m), 2.05-1.93 (8H, m), 1.63-1.45 (16H, m), 1.05-0.98 (12H, m) ppm. .sup.13C NMR δc: (100 MHz, CDCl.sub.3) 161.7, 149.4, 148.8, 145.9, 145.4, 142.9, 140.8, 140.2, 134.7, 133.2, 129.1, 128.7, 128.0, 127.9, 127.6, 127.1, 126.9, 124.8, 124.7, 124.6, 124.0, 123.6, 123.4, 116.4, 112.7, 108.1, 107.2, 103.7, 103.6, 72.5, 70.7, 70.4, 70.1, 69.9, 69.8, 69.7, 69.0, 50.6, 29.32, 29.30, 29.17, 28.54, 28.46, 28.43, 22.75, 22.71, 14.27, 14.21 ppm. MALDI m/z: 912.9 ([M].sup.+ 100%), 913.9 ([M+H].sup.+ 90%). Elemental analysis Found: C, 73.36; H, 7.55; N, 6.12%. C.sub.55H.sub.68N.sub.4O.sub.8 requires C, 73.34; H, 7.51; N, 6.14%.

EXAMPLE 4—SYNTHESIS OF COMPOUND 41

[0279] Compound 41 was synthesised using the following method. A slurry of Precursor 8 (100 mg, 0.13 mmol) and K.sub.2CO.sub.3 (37 mg, 0.26 mmol) in MeCN (5 mL) was heated at reflux with a CaCl.sub.2 drying tube for 0.5 h followed by addition of 2-(2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (101 mg, 0.26 mg). The resultant slurry was further heated at reflux for 24 h h. The reaction mixture was allowed to cool to room temperature and the precipitate filtered off via suction filtration. The solvent was evaporated from the filtrate to dryness in vacuo and the crude solid was purified by purified via flash column chromatography (silica, silica, 50% EtOAc: 50% n- hexane) to afford Compound 38 as a yellow solid (15 mg, 13%).

[0280] The name for Compound 41 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)ethan-1-amine.

[0281] Compound 41 had the following characterisation data: .sup.1H NMR δ.sub.H: (300 MHz, CDCl.sub.3) 10.13 (1H, s), 8.82 (1H, s), 8.50 (1H, dd, J 8.6, 1.7), 8.07-8.03 (2H, m), 7.91-7.81 (5H, m), 7.57-7.57 (2H, m), 4.58 (2H, t, J 5.5 Hz), 4.43 (2H, t, J 6.7 Hz), 4.28-4.20 (6H, m), 4.14-4.10 (2H, m), 3.86-3.82 (2H, m), 3.69-3.57 (4H, m), 3.17-3.19 (2H, m), 2.04-1.92 (8H, m), 1.63-1.44 (16H, m), 1.04-0.97 (12H, m) ppm. .sup.13C NMR δc: (100 MHz, CDCl.sub.3) 161.7, 149.4, 148.8, 145.9, 145.4, 142.9, 140.8, 140.2, 134.7, 133.2, 129.1, 128.7, 128.0, 127.9, 127.6, 127.1, 126.9, 124.8, 124.7, 124.6, 124.0, 123.6, 123.4, 116.4, 112.7, 108.1, 107.2, 103.7, 103.6, 72.3, 70.6, 70.3, 70.0, 69.9, 69.8, 69.7, 69.0, 42.5, 29.4, 29.3, 29.2, 28.5, 28.5, 28.4, 22.75, 22.7, 14.3, 14.2 ppm. MALDI m/z: 886.5 ([M].sup.+ 100%), 887.6 ([M+H].sup.+ 70%).

EXAMPLE 7—USE OF COMPOUND 39 AS A BIOSENSOR WITH AN ANTIBODY

[0282] Referring now to FIG. 4, there is shown a schematic route 3 to conjugating an antibody A to a luminescent compound LC to produce a conjugated antibody A-LC according to an Example of the invention.

[0283] The luminescent compound LC used in this example was Compound 39. Compound 39 was activated towards conjugation in the following method. A solution was prepared containing the following components: [0284] 10 μL of Compound 39 dissolved in DMSO at a concentration of 3.8 mg/ml (4.2 mM); [0285] 10 μL of TSTU (N,N,N′,N′-tetramethyl-O—(N-succinimidyl)uronium tetrafluoroborate) at a concentration of 1.4 μg/ml (4.7 mM); [0286] 1 μL triethylamine to a final concentration of 0.67 μL/mL (6.6 μM).

[0287] The resulting solution was held at room temperature on a shaking incubator for 20 minutes to produce the “biosensor solution” containing the luminescent compound, Compound 39 comprising an NHS (N-hydroxysuccinimide) ester instead of a carboxylic acid functional group.

[0288] The antibody A was prepared in the following method. 50 μL of the Antibody (2 mg/mL (˜14 μM)) was added to an Amicon(RTM) Ultra-0.5 ml filter containing a 30 kDa cut-off filter. The antibody buffer was exchanged for 0.1 M sodium borate buffer, pH 8.5, using two rounds of dilution/concentration with 400 μL additions of the borate buffer to produce the “antibody solution”.

[0289] The antibody A was conjugated to the luminescent compound LC in the following method. The “antibody solution” and the “biosensor solution” were directly combined and allowed to react for 1 hr at room temperature. The resulting conjugated antibody A-LC was purified from unreacted luminescent compound using a standard desalting column (ZebaSpin, 7 kDa MWCO), prior to characterisation of the labelled conjugate by UV-vis spectroscopy.

[0290] Referring now to FIG. 5, there is shown a series of spectra showing the conjugation of the antibody A to the luminescent compound LC according to this Example of the invention. Spectra 51 is taken of the antibody A alone. Spectra 52 is taken of the luminescent compound LC (Compound 39) alone. Spectra 53 is taken of the antibody conjugated to the luminescent compound A-LC.

[0291] Referring now to FIG. 6, there is shown a series of images showing the conjugation of an antibody to a luminescent compound according to this Example of the invention. Image 61 is of the luminescent compound LC alone, image 62 is of a control sample comprising an antibody conjugated to Alexa488(RTM) according to a comparative Example of the invention, and image 63 is of the antibody conjugated to the luminescent compound A-LC according to Example 7 of the invention.

EXAMPLE 8—SYNTHESIS OF COMPOUND 44

[0292] Compound 44 was synthesised using the following method. A solution of Precursor 2 (100 mg, 0.132 mmol), 3-fluorobenzoyl chloride (92 mg, 0.658 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N.sub.2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo purified via flash column chromatography (silica, 60% CH.sub.2Cl.sub.2: 40% n- hexane) to afford an intermediate as a brown solid (19 mg, 18 %).

[0293] The intermediate (3-fluoro-N-(2,3,6,7,10,11-hexakis(pentyloxy)triphenylen-1-yl)benzamide) (100 mg, 0.11 mmol) was dissolved in xylenes (10 mL) and Woollins reagent (117.8 mg, 0.22 mmol) was added to the flask. The reaction was stirred at reflux for 24 h before being cooled to room temperature causing the formation of a grey precipitate. The contents of the flask were filtered through filter paper and the filtrate recovered. The filtrate was evaporated to dryness and purified by column chromatography (silica, 40% dichloromethane:hexane) and (silica, 1% acetone : hexane) yielding 8-(3-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d][1,3]selenazole as a yellow solid (1.8 mg).

[0294] The name for Compound 44 is 8-(3-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d][1,3]selenazole.

[0295] Compound 44 had the following characterisation data: .sup.1H NMR δ.sub.H (500 MHz, CDCl.sub.3) 10.40 (1H, s), 8.00 (1H, s), 7.97 (1H, d, J 9.8 Hz), 7.95 (1H, s), 7.92 (1H, s), 7.90 (1H, d, J 7.8 Hz), 7.87 (1H, s), 7.49 (1H, dd, J 14.1, 8.5 Hz), 7.24-7.21 (1H, m), 4.45 (2H, t, J 6.8 Hz), 4.42 (2H, t, J 6.7 Hz), 4.28 (6H, dt, J 13.4, 6.6 Hz), 2.06-1.94 (10H, m), 1.61-1.44 (20H, m), 1.03-0.93 (15H, m) ppm. TOF LD.sup.+ m/z=860.4 ([M+2+H].sup.+ 30%), 859.4 ([M+2].sup.+ 60%), 858.4 ([M+H].sup.+ 90%), 857.4 ([M].sup.+ 100%), 856.4 ([M−2+H].sup.+ 40%), 855.4 ([M−2].sup.+ 60%), 854.4 ([M−3].sup.+ 30%), 825.5 ([TpOxPhmF+MeOH].sup.+), 793.4 ([TpOxPhmF].sup.+).

[0296] It will be appreciated by those skilled in the art that any number of combinations of the aforementioned features and/or those shown in the appended drawings provide clear advantages over the prior art and are therefore within the scope of the invention described herein.

[0297] Some aspects and embodiments of the invention are defined by the following clauses:

[0298] 1. A luminescent molecule represented by the following general formula:

##STR00022## [0299] wherein R represents an aromatic group and/or an aliphatic group; [0300] p is an integer of 1 or 2; [0301] q and s are independently integers of 1, 2, 3, or 4; [0302] Y.sup.1, Y.sup.2, and Y.sup.3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g. a substituted or unsubstituted group comprising a polyglycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; [0303] Y.sup.1, Y.sup.2, and/or Y.sup.3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

[0304] 2. The luminescent molecule according to clause 1, represented by the following general formula:

##STR00023## [0305] wherein R represents an aromatic group and/or an aliphatic group; [0306] Y.sup.4, Y.sup.5, Y.sup.6, Y.sup.7, Y.sup.8, Y.sup.9, Y.sup.10, Y.sup.11, Y.sup.12, Y.sup.13 may independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g. a substituted or unsubstituted group comprising a polyglycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; [0307] two or more of Y.sup.4, Y.sup.5, Y.sup.6, Y.sup.7, Y.sup.8, Y.sup.9, Y.sup.10, Y.sup.11, Y.sup.12, Y.sup.13 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

[0308] 3. A luminescent compound according to any preceding clause, wherein one or more or all of Y.sup.1 to Y.sup.13 represent or comprise an alkyl group, e.g. a straight, linear chain alkyl group or a branched chain alkyl group.

[0309] 4. A luminescent compound according to clause 3, wherein the alkyl group comprises between 1 and 20 carbon atoms, e.g. between 2 and 18 carbon atoms, 3 and 17 carbon atoms, 4 and 16 carbon atoms.

[0310] 5. A luminescent compound according to clause 3 or 4, wherein one or more or all of Y.sup.1 to Y.sup.3, or Y.sup.4 to Y.sup.13, independently represent an alkoxy group, e.g. an OR′ group wherein R′ is a straight or branched alkyl chain.

[0311] 6. A luminescent compound according to clause 5, wherein one or more or all of Y.sup.1 to Y.sup.3, or Y.sup.4 to Y.sup.13 consist of a straight chain alkoxy group selected from one or more of a OCH.sub.3, OC.sub.2H.sub.5, OC.sub.3H.sub.7, OC.sub.4H.sub.9, OC.sub.5H.sub.11, OC.sub.6H.sub.13, OC.sub.7H.sub.15, OC.sub.8H.sub.17, OC.sub.10H.sub.19, or OC.sub.10H.sub.21 group or combinations thereof.

[0312] 7. A luminescent compound according to clause 6, wherein Y.sup.4, Y.sup.7, Y.sup.8, Y.sup.11, Y.sup.12 each each represent an alkoxyl group, e.g. an OR′ group.

[0313] 8. A luminescent compound according to clause 7, wherein Y.sup.4, Y.sup.7, Y.sup.8, Y.sup.11 each represent an OC.sub.5H.sub.11 group.

[0314] 9. A luminescent compound according to clauses 2 to 8, wherein one or more or all of Y.sup.5, Y.sup.6, Y.sup.9, Y.sup.10, Y.sup.13 represent a hydrogen atom.

[0315] 10. A luminescent compound according to any preceding clause, represented by the following general formula:

##STR00024## [0316] wherein R represents an aromatic group and/or an aliphatic group; [0317] J.sup.1, J.sup.2, J.sup.3, J.sup.4, J.sup.5 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g. a substituted or unsubstituted group comprising a polyglycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; [0318] wherein J.sup.1 and J.sup.2, or J.sup.3 and J.sup.4 may combine together to form a condensed ring (e.g. a condensed aromatic ring); [0319] A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 independently represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group.

[0320] 11. A luminescent compound according to clause 10, wherein one or more or all of A.sup.1 to A.sup.5 comprise an alkyl group.

[0321] 12. A luminescent compound according to clause 10 or 11, wherein the alkyl group(s) consist of a straight chain alkyl group selected from one or more of a CH.sub.3, C.sub.2H.sub.5, C.sub.3H.sub.7, C.sub.4H.sub.9, C.sub.5H.sub.11, C.sub.6H.sub.13, C.sub.7H.sub.15, C.sub.8H.sub.17, C.sub.9H.sub.19, or C.sub.10H.sub.21 alkyl group.

[0322] 13. A luminescent compound according to clause 10, 11, or 12, wherein one or more of J.sup.1 to J.sup.5 independently represent a hydrogen atom.

[0323] 14. A luminescent compound according to any of clauses 10 to 13, wherein J.sup.1, J.sup.2, J.sup.3, J.sup.4, J.sup.5 each represent a hydrogen atom, and A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 each represent an alkyl chain, e.g. a C.sub.5H.sub.11 moiety.

[0324] 15. A luminescent compound according to any preceding clause, represented by the formula of Compound 44 of this specification.

[0325] 16. A luminescent compound according to clause 1 or 2, represented by the following general formula:

##STR00025## [0326] wherein R.sup.1 and R.sup.2 independently represents an aromatic group and/or an aliphatic group; p and q are independently an integer of 1 to 2; [0327] s is an integer of 1 to 4; [0328] Y.sup.1, Y.sup.2, and Y.sup.3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g. a substituted or unsubstituted group comprising a polyglycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; [0329] Y.sup.1, Y.sup.2, or Y.sup.3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

[0330] 17. A luminescent compound according to clause 1 or 2, represented by the following general formula:

##STR00026## [0331] wherein R.sup.1, R.sup.2, R.sup.3 independently represent an aromatic group and/or an aliphatic group; p, q, and s are each independently an integer of 1 to 2; [0332] Y.sup.1, Y.sup.2, and Y.sup.3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g. a substituted or unsubstituted group comprising a polyglycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group.

[0333] 18. A luminescent compound according to clause 1 or 2, represented by the following general formula:

##STR00027## [0334] wherein R independently represents an aromatic group and/or an aliphatic group; [0335] q is independently an integer of 1 to 3; [0336] s is independently an integer of 1 to 4; [0337] t is independently an integer of 1 to 4; [0338] Y.sup.2, Y.sup.3, and Y.sup.14 and J independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g. a substituted or unsubstituted group comprising a polyglycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; [0339] Y.sup.2, Y.sup.3, and/or Y.sup.14 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

[0340] 19. A luminescent compound according to clause 18, represented by the following general formula:

##STR00028## [0341] wherein R independently represents an aromatic group and/or an aliphatic group; [0342] Y.sup.15, Y.sup.16, Y.sup.17, Y.sup.18, Y.sup.19, Y.sup.20, Y.sup.21, Y.sup.22, Y.sup.23, Y.sup.24, Y.sup.25, Y.sup.26 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g. a substituted or unsubstituted group comprising a polyglycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; [0343] two or more of Y.sup.15, Y.sup.16, Y.sup.17, Y.sup.18, Y.sup.19, Y.sup.20, Y.sup.21, Y.sup.22, Y.sup.23, Y.sup.24, Y.sup.25, Y.sup.26 combine together to form a condensed ring (e.g. a condensed aromatic ring).

[0344] 20. A luminescent compound according to clause 19, wherein one or more or all of Y.sup.15, Y.sup.17, Y.sup.18, Y.sup.20, Y.sup.21, Y.sup.24, Y.sup.25 each represent an OR′ group, e.g. an OC.sub.5H.sub.11 group or an OCH.sub.3 group.

[0345] 21. A luminescent compound according to clause 19 or 20, wherein one or more or all of Y.sup.16, Y.sup.19, Y.sup.22, Y.sup.23, Y.sup.26 each represent a hydrogen atom.