US6005113A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Long wavelength dyes for infrared tracing
Assignee: Molecular Probes Inc
•
Filing: 1997-05-14
•
Granted: 1999-12-21
•
Expires: 2017-05-14
Abstract
Abstract The invention relates to fluorescent dyes that are substituted or unsubstituted derivatives of 1-(isoindolyl)methylene-isoindole that are bound through both isoindole nitrogens to a boron difluoride moiety, forming a fluorescent dibenzopyrrometheneboron difluoride compound ##STR1## that is further substituted by bathochromic substituents that are aryl or heteroaryl moieties further substituted by an additional aryl or heteroaryl, that is itself optionally further substituted by an additional aryl or heteroaryl. These aryl and heteroaryl groups are separated by a covalent bond, or by an ethenyl, butadienyl or hexatrienyl linkage. The dyes of the invention are particularly useful as labels for carriers, particularly polymeric microparticles. The resulting microparticles have a long-wavelength fluorescence emission, and possess utility for tracing flow in biological systems, particularly in tracing blood flow.
Inventors
- 👤 Yexin Wu
- 👤 Dieter H. Klaubert
- 👤 Hee Chol Kang
- 👤 Yu-zhong Zhang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 06:10
CPC Classifications
C; C09; C09B; C09B57/00; C09B57/10; C09K; C09K11/00; C09K11/06; Y; Y10; Y10S; Y10S436/00; Y10S436/805
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
779 words
A compound of the formula: ##STR24## wherein R 5 and R 5' are bathochromic substituents independently having the formula -α-K-β; wherein K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; α is a phenyl a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety, that is optionally further substituted by an -L-γ; wherein each L is independently a single covalent bond or an ethenyl, butadienyl, or hexatrienyl moiety; γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkoxycarbonyl, acyloxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, -J-ARYL, -J-HETEROARYL, or a polymerizable moiety; or two adjacent substituents are fused to form a BENZO or a HETERO; wherein each J is independently a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to an additional six-membered aromatic ring, or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; R 6 is H, alkyl, cycloalkyl having 3-6 carbons, perfluoroalkyl, an ARYL, a HETEROARYL, or CN; wherein the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched, saturated or unsaturated; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, cyano, amino, hydroxy, carboxy, alkali or ammonium salt of carboxy, mercapto, sulfo, alkali or ammonium salt of sulfo, or a polymerizable moiety.
Claim 2
Dependent Claim
779 words
A compound of the formula: ##STR24## wherein R 5 and R 5' are bathochromic substituents independently having the formula -α-K-β; wherein K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; α is a phenyl a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety, that is optionally further substituted by an -L-γ; wherein each L is independently a single covalent bond or an ethenyl, butadienyl, or hexatrienyl moiety; γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkoxycarbonyl, acyloxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, -J-ARYL, -J-HETEROARYL, or a polymerizable moiety; or two adjacent substituents are fused to form a BENZO or a HETERO; wherein each J is independently a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to an additional six-membered aromatic ring, or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; R 6 is H, alkyl, cycloalkyl having 3-6 carbons, perfluoroalkyl, an ARYL, a HETEROARYL, or CN; wherein the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched, saturated or unsaturated; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, cyano, amino, hydroxy, carboxy, alkali or ammonium salt of carboxy, mercapto, sulfo, alkali or ammonium salt of sulfo, or a polymerizable moiety.
Claim 3
Dependent Claim
345 words
A compound, as claimed in claim 1, wherein R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, alkylthio, -J-ARYL, -J-HETEROARYL, or two adjacent substituents are fused to form a BENZO or a HETERO; wherein each α, β, and γ is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to additional six-membered aromatic rings, or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio.
Claim 4
Dependent Claim
34 words
A compound, as claimed in claim 2, wherein at R 1 =R 1' , R 2 =R 2' , R 3 =R 3' , R 4 =R 4' and R 5 =R 5' .
Claim 5
Dependent Claim
23 words
A compound, as claimed in claim 2, wherein α, β, and γ are independently a phenyl, a thienyl, a furyl, or a pyrrolyl.
Claim 6
Dependent Claim
38 words
A compound, as claimed in claim 2, wherein α is a thienyl; β is a para-alkoxyphenyl or a thienyl; γ is a para-alkoxyphenyl or a thienyl; and K and L are independently a single covalent bond or ethenyl.
Claim 7
Dependent Claim
16 words
A compound, as claimed in claim 5, wherein R 3 and R 3' are each alkoxy.
Claim 8
Dependent Claim
588 words
A composition, comprising: a compound of the formula: ##STR25## wherein R 5 and R 5' are bathochromic substituents independently having the formula -α-K-β; wherein K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; and α is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio, that is optionally further substituted by an -L-γ; wherein L is a single covalent bond, or L is an ethenyl, butadienyl, or hexatrienyl moiety; and γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, alkylthio, -J-ARYL, -J-HETEROARYL, or two adjacent substituents are fused to form a BENZO or a HETERO; wherein J is a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to additional six-membered aromatic rings, or is fused to one 5- or 6-membered heteroaromatic ring, the heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N, or S in any combination, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; R 6 is H, alkyl, cycloalkyl having 3-6 carbons, perfluoroalkyl, an ARYL, a HETEROARYL, or CN; wherein the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, or cyano incorporated covalently or noncovalently within a polymeric matrix.
Claim 9
Dependent Claim
588 words
A composition, comprising: a compound of the formula: ##STR25## wherein R 5 and R 5' are bathochromic substituents independently having the formula -α-K-β; wherein K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; and α is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio, that is optionally further substituted by an -L-γ; wherein L is a single covalent bond, or L is an ethenyl, butadienyl, or hexatrienyl moiety; and γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, alkylthio, -J-ARYL, -J-HETEROARYL, or two adjacent substituents are fused to form a BENZO or a HETERO; wherein J is a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to additional six-membered aromatic rings, or is fused to one 5- or 6-membered heteroaromatic ring, the heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N, or S in any combination, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; R 6 is H, alkyl, cycloalkyl having 3-6 carbons, perfluoroalkyl, an ARYL, a HETEROARYL, or CN; wherein the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, or cyano incorporated covalently or noncovalently within a polymeric matrix.
Claim 10
Dependent Claim
17 words
A composition, as claimed in claim 7, wherein the compound is incorporated noncovalently within the polymeric matrix.
Claim 11
Dependent Claim
36 words
A composition, as claimed in claim 7, wherein for the compound R 1 =R 1' , R 2 =R 2' , R 3 =R 3' , R 4 =R 4' and R 5 =R 5' .
Claim 12
Dependent Claim
60 words
A composition, as claimed in claim 7, wherein the polymeric matrix comprises a polymer or copolymer of a styrene, a divinyl benzene, an acrylate or methacrylate ester, an acrylic acid or methacrylic acid, an acrylamide or methacrylamino, an acrylonitrile or methacrylonitrile, a vinyl halide, a vinylidene halide, a vinylidene ester, a vinylidene ether, an alkene, an epoxide or a urethane.
Claim 13
Dependent Claim
29 words
A composition, as claimed in claim 10, wherein the polymeric matrix comprises a polymer or copolymer of polystyrene that is optionally crosslinked through the incorporation of divinylbenzene during polymerization.
Claim 14
Dependent Claim
36 words
A composition, as claimed in claim 11, wherein for the compound R 1 =R 1' , R 2 =R 2' , R 3 =R 3' , R 4 =R 4' and R 5 =R 5' .
Claim 15
Dependent Claim
25 words
A composition, as claimed in claim 7, wherein the polymeric matrix is a microsphere having a diameter of about 0.01 μm to about 100 μm.
Claim 16
Dependent Claim
21 words
A composition, as claimed in claim 13, wherein the microsphere has a diameter of about 1 μm to about 25 μm.
Claim 17
Dependent Claim
21 words
a composition, as claimed in claim 13, wherein the microsphere is surface modified with a member of a specific binding pair.
Claim 18
Dependent Claim
43 words
A composition, as claimed in claim 12, wherein for the compound α is a thienyl; β is a para-alkoxyphenyl or a thienyl; γ is a para-alkoxyphenyl or a thienyl; and K and L are independently a single covalent bond or an ethenyl moiety.
Claim 19
Dependent Claim
13 words
A composition, as claimed in claim 7, wherein the polymeric matrix is biodegradeable.
Claim 20
Independent Claim
813 words
A method of tracing transport within a sample, comprising: a) adding to the sample a composition comprising a dye compound of the formula ##STR26## wherein R 5 and R 5' are bathochromic substituents independently having the formula -α-K-β; wherein K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; α is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety, that is optionally further substituted by an -L-γ; wherein each L is independently a single covalent bond an ethenyl, butadienyl, or hexatrienyl moiety; γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, sulfo alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkoxycarbonyl, acyloxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, -J-ARYL, -J-HETEROARYL, or a polymerizable moiety; or two adjacent substituents are fused to form a BENZO or a HETERO; wherein each J is independently a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to an additional six-membered aromatic ring, or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; R 6 is H, alkyl, cycloalkyl having 3-6 carbons, perfluoroalkyl, an ARYL, a HETEROARYL, or CN; wherein the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched, saturated or unsaturated; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, cyano, amino, hydroxy, carboxy, alkali or ammonium salt of carboxy, mercapto, sulfo, alkali or ammonium salt of sulfo, or a polymerizable moiety; and b) generating a fluorescence response from the dye compound to indicate transport within the sample.
Claim 21
Independent Claim
813 words
A method of tracing transport within a sample, comprising: a) adding to the sample a composition comprising a dye compound of the formula ##STR26## wherein R 5 and R 5' are bathochromic substituents independently having the formula -α-K-β; wherein K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; α is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety, that is optionally further substituted by an -L-γ; wherein each L is independently a single covalent bond an ethenyl, butadienyl, or hexatrienyl moiety; γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, sulfo alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkoxycarbonyl, acyloxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, -J-ARYL, -J-HETEROARYL, or a polymerizable moiety; or two adjacent substituents are fused to form a BENZO or a HETERO; wherein each J is independently a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to an additional six-membered aromatic ring, or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; R 6 is H, alkyl, cycloalkyl having 3-6 carbons, perfluoroalkyl, an ARYL, a HETEROARYL, or CN; wherein the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched, saturated or unsaturated; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, cyano, amino, hydroxy, carboxy, alkali or ammonium salt of carboxy, mercapto, sulfo, alkali or ammonium salt of sulfo, or a polymerizable moiety; and b) generating a fluorescence response from the dye compound to indicate transport within the sample.
Claim 22
Dependent Claim
599 words
A method, as claimed in claim 18, wherein the composition comprises a polymeric matrix that incorporates, either covalently or noncovalently, a dye compound of the formula: ##STR27## wherein R 5 and R 5' are bathochromic substituents independently having the formula -α-K-β; wherein K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; and α is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio, that is optionally further substituted by an -L-γ; wherein L is a single covalent bond, or L is an ethenyl, butadienyl, or hexatrienyl moiety; and γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, alkyl, perflouroalkyl, alkoxy, alkylthio, -J-ARYL, -J-HETEROARYL, or two adjacent substituents are fused to form a BENZO or a HETERO; wherein J is a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETEROARYL is independently a 5-or 6-membered aromatic heterocycle that is optionally fused to additional six-membered aromatic rings, or is fused to one 5- or 6-membered heteroaromatic ring, the heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , up to a maximum of four BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' , and that is optionally and independently substituted by H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, or alkylthio; R 6 is H, alkyl, cycloalkyl having 3-6 carbons, perfluoroalkyl, an ARYL, a HETEROARYL, or CN; wherein the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, or cyano.
Claim 23
Dependent Claim
36 words
A method, as claimed in claim 19, wherein the dye compound is incorporated noncovalently within the polymeric matrix; and the polymeric matrix is a microsphere having a diameter of about 0.01 μm to about 100 μm.
Claim 24
Dependent Claim
101 words
A method, as claimed in claim 20, wherein R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , and R 4' are independently H, halogen, cyano, alkyl, perfluoroalkyl, alkoxy, alkylthio, -J-ARYL, -J-HETEROARYL, or two adjacent substituents are fused to form a BENZO or a HETERO; R 1 =R 1' , R 2 =R 2' , R 3 =R 3' , R 4 =R 4' and R 5 =R 5' ; and the step of generating a fluorescence response comprises illuminating the dye compound at a wavelength longer than 700 nm.
Claim 25
Dependent Claim
26 words
A method, as claimed in claim 20, wherein the step of generating a fluorescence response is performed using a microscope, a fluorometer, or a flow cytometer.
Claim 26
Dependent Claim
25 words
A method, as claimed in claim 20, wherein the polymeric matrix is a microsphere having a diameter of about 1 μm to about 25 μm.
Claim 27
Dependent Claim
60 words
A method, as claimed in claim 19, wherein the polymeric matrix comprises a polymer or copolymer of a styrene, a divinyl benzene, an acrylate or methacrylate ester, an acrylic acid or methacrylic acid, an acrylamide or methacrylamino, an acrylonitrile or methacrylonitrile, a vinyl halide, a vinylidene halide, a vinylidene ester, a vinylidene ether, an alkene, an epoxide or a urethane.
Claim 28
Dependent Claim
29 words
A method, as claimed in claim 24, wherein the polymeric matrix comprises a polymer or copolymer of polystyrene that is optionally crosslinked through the incorporation of divinylbenzene during polymerization.
Claim 29
Dependent Claim
21 words
A method, as claimed in claim 20, wherein the sample is a biological sample that comprises a circulatory or respiratory system.
Claim 30
Dependent Claim
26 words
A method, as claimed in claim 26, wherein the sample comprises a circulatory system, and transport occurs due to movement of fluid within the circulatory system.
Claim 31
Dependent Claim
25 words
A method, as claimed in claim 26, wherein sample comprises a respiratory system, and transport occurs due to movement of gas within the respiratory system.
Claim 32
Dependent Claim
22 words
A method, as claimed in claim 26, wherein the resultant distribution of the fluorescence response indicates the circulatory or respiratory system volume.
Claim 33
Dependent Claim
23 words
A method, as claimed in claim 26, wherein the resultant distribution of the fluorescence response indicates the circulatory or respiratory system flow characteristics.
Claim 34
Dependent Claim
18 words
A method, as claimed in claim 26, wherein the sample is an organ, a tissue or an animal.
Claim 35
Dependent Claim
13 words
A method, as claimed in claim 27, wherein the sample is an animal.
Claim 36
Dependent Claim
31 words
A method, as claimed in claim 27, wherein said microsphere has a diameter of from 0.1 to 40 micrometers, and the compound is added to the sample as an aqueous suspension.
Claim 37
Dependent Claim
31 words
A method, as claimed in claim 27, wherein the sample is an animal having a circulatory system, and the resultant distribution of the fluorescence response indicates blood flow in the animal.
Claim 38
Dependent Claim
46 words
A method, as claimed in claim 27, wherein the microsphere is surface modified with a member of a specific binding pair, and the resultant distribution of the fluorescence response indicates the location of a binding pair member complementary to the member of a specific binding pair.
Claim 39
Dependent Claim
30 words
A method, as claimed in claim 28, wherein said microsphere has a diameter of from 0.1 to 5 micrometers, and the compound is added to the sample as an aerosol.
Claim 40
Dependent Claim
31 words
A method, as claimed in claim 28, wherein the sample is an animal having a respiratory system, and the resultant distribution of the fluorescence response indicates regional ventilation in the animal.
Claim 41
Dependent Claim
708 words
A compound, having the formula ##STR28## wherein R 1 , R 2 , R 3 , and R 4 are independently H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkoxycarbonyl, acyloxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, -J-ARYL, -J-HETEROARYL, or a polymerizable moiety; or two adjacent substituents are fused to form a BENZO or a HETERO; wherein J is a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; and α is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety, that is optionally further substituted by an -L-γ; wherein each L is a single covalent bond or an ethenyl, butadienyl, or hexatrienyl moiety; γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to additional six-membered aromatic rings, or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , and R 4 , up to a maximum of two BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , and R 4 that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched, saturated or unsaturated; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, cyano, amino, hydroxy, carboxy, alkali or ammonium salt of carboxy, mercapto, sulfo, alkali or ammonium salt of sulfo, or a polymerizable moiety.
Claim 42
Dependent Claim
708 words
A compound, having the formula ##STR28## wherein R 1 , R 2 , R 3 , and R 4 are independently H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkoxycarbonyl, acyloxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, -J-ARYL, -J-HETEROARYL, or a polymerizable moiety; or two adjacent substituents are fused to form a BENZO or a HETERO; wherein J is a single covalent bond, --O--, --NH--, --(C═O)--NH--, --NH--(C═O)--; or J is an ethenyl, butadienyl, or hexatrienyl moiety; K is a single covalent bond, or K is an ethenyl, butadienyl, or hexatrienyl moiety; and α is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; β is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety, that is optionally further substituted by an -L-γ; wherein each L is a single covalent bond or an ethenyl, butadienyl, or hexatrienyl moiety; γ is a phenyl, a naphthyl, a thienyl, a furyl, a pyrrolyl or a pyridyl that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; provided that at least one α, β or γ is a thienyl, a furyl, a pyrrolyl or a pyridyl; each ARYL is independently an aromatic or polyaromatic substituent containing 1 to 4 aromatic rings and no heteroatoms, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino; alkylamido or a polymerizable moiety; each HETEROARYL is independently a 5- or 6-membered aromatic heterocycle that is optionally fused to additional six-membered aromatic rings, or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings contain at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N or S in any combination, and is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each BENZO is independently --CR 7 ═CR 8 --CR 9 ═CR 10 -- bonded to any two adjacent positions of R 1 , R 2 , R 3 , and R 4 , up to a maximum of two BENZO moieties; wherein R 7 , R 8 , R 9 and R 10 are independently selected from H, halogen, cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; each HETERO is independently a combination of 1 to 3 carbon atoms and 1 to 3 hetero atoms selected from the group consisting of O, S and N to form a fused 5- or 6-membered heteroaromatic ring that is bonded to any two adjacent positions of R 1 , R 2 , R 3 , and R 4 that is optionally and independently substituted by H, halogen, cyano, sulfo, alkali or ammonium salt of sulfo, carboxy, alkali or ammonium salt of carboxy, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, alkylamido, or a polymerizable moiety; the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups independently have 1-18 carbon atoms in an arrangement that is either linear or branched, saturated or unsaturated; and the alkyl portions of all alkyl, perfluoroalkyl, alkoxy, alkylthio, monoalkylamino, dialkylamino and alkylamido groups are independently and optionally further substituted by H, halogen, cyano, amino, hydroxy, carboxy, alkali or ammonium salt of carboxy, mercapto, sulfo, alkali or ammonium salt of sulfo, or a polymerizable moiety.
References Cited (Backward Citations)
US4326008A
Cited
US4774339A
Cited
US5248782A
Cited
US5338854A
Cited
US5187288A
Cited
US5274113A
Cited
US5326692A
Cited
US5326692B1
Cited
US5573909A
Cited
US5433896A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2002-12-20 | 2003-06-21 | 2003-12-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-12-20 | 2007-06-21 | 2007-12-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-12-20 | 2011-06-21 | 2011-12-21 | $7700.00 | Window Closed / Lapsed |