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US 5,847,114 AGranted
Poly-substituted phthalocyantines
AssigneeZeneca Limited
InventorsDean Thetford, Peter Gregory
Life of this patent
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Abstract
The use of substituted phthalocyanines for the generation of singlet oxygen in which at least one of the peripheral carbon atoms in the 1-16 positions of the phthalocyanine nucleus (M.sub.k Pc) of Formula (1): ##STR1## wherein: M is selected from H, metal, halometal, oxymetal and hydroxymetal; and k is the inverse of 1/2 of the valency of M; is linked via an oxygen atom to an aromatic radical and the remaining peripheral carbon atoms are unsubstituted or substituted by any combination of atoms or groups and sulphonated derivatives thereof provided that the phthalocyanine absorbs electromagnetic radiation at a wavelength from 650 nm to 800 nm.
Claims12
A compound of the Formula ( 3):
- M.sub.k Pc(O-R.sup.1).sub.a X.sub.b Formula ( 3)
- wherein:
- M.sub.k Pc is as defined in Formula (1):
- ##STR5## wherein:
- M is selected from the group consisting of Zn, ClAl, OHAl, ClRh, OHRh, Clln, Brln OHln, ClGa, OHGa, Pt, Pd, Li, Na, K, Ca, Ba, Mg, ClSc and OHSc;
- k is the inverse of 1/2 of the valency of M.sub.k ;
- R.sup.1 is selected from the group consisting of phenyl, naphthyl, pyridyl, thiophenyl, furanyl, quinolinyl, thiazolyl, benzothiazolyl, pyrimidyl, each of which independently is unsubstituted or substituted by a substituent selected from the group consisting of C.sub.1-20 -alkyl, C.sub.1-20 -alkoxy, C.sub.2-20 -alkenyl, C.sub.1-20 -alkylthiol, C.sub.1-20 -alkoxycarbonyl, hydroxy C.sub.1-4 -alkoxy, phenyl, benzyl, phenylthio, fluoro, chloro, bromo, --CN, --NO.sub.2, --CF.sub.3, --COR.sup.2, --COOR.sup.2, --CONR.sup.2 R.sup.3, --SO.sub.2 R.sup.2, --SO.sub.2 NR.sup.2 R.sup.3, --NR.sup.2 R.sup.3 and --OR.sup.2 in which R.sup.2 and R.sup.3 are each independently H, C.sub.1-4 -alkyl or phenyl;
- X is halogen or H;
- a is an integer selected from 4, 8, 12 and 16;
- b is an integer from 0 to 15;
- a+b is equal to 16;
- provided that when M is ClGa or Clln, X is halogen and a is 4, 8, or 12;
- and provided that when M is AlCl, a is 16;
- except for the compounds:
- GaCl Pc(Ph--O).sub.8 Cl.sub.8,
- ZnPc(Ph--O).sub.4 H.sub.12,
- ZnPc(4-NO.sub.2 Ph--O).sub.4 H.sub.12,
- ZnPc(4-NH.sub.2 Ph--O).sub.4 H.sub.12,
- ZnPc(HOPh--O).sub.4 H.sub.12,
- MgPc(2-Br-4-Me (CH.sub.2).sub.4 Ph--O).sub.4 H.sub.12,
- ZnPc(4-Me(CH.sub.2).sub.6 Ph--O).sub.4 H.sub.12 and
- Li.sub.2 Pc(2-naphthyl-O).sub.8 H.sub.8.
19 more elements
A compound of the Formula (3):
- M.sub.k Pc(O--R.sup.1).sub.a X.sub.b Formula ( 3)
- wherein:
- M.sub.k Pc is as defined in Formula (1):
- ##STR6## wherein:
- M is selected from the group consisting of Zn, ClAl, OHAl, ClRh, OHRh, Clln, Brln OHln, ClGa, OHGa, Pt, Pd, Li, Na, K, Ca, Ba, Mg, ClSc and OHSc;
- k is the inverse of 1/2 of the valency of M.sub.k ;
- R.sup.1 is selected from the group consisting of phenyl, naphthyl, pyridyl, thiophenyl, furanyl, quinolinyl, thiazolyl, benzothiazolyl, pyrimidyl, each of which independently is unsubstituted or substituted by a substituent selected from the group consisting of C.sub.1-20 -alkyl, C.sub.1-20 -alkoxy, C.sub.2-20 -alkenyl, C.sub.1-20 -alkylthiol, C.sub.1-20 -alkoxycarbonyl, hydroxy C.sub.1-4 -alkoxy, phenyl, benzyl, phenylthio, fluoro, chloro, bromo, --CN, --NO.sub.2, --CF.sub.3, --COR.sup.2, --COOR.sup.2.sub.1 --CONR.sup.2 R.sup.3, --SO.sub.2 R.sup.2, --SO.sub.2 NR.sup.2 R.sup.3.sub.1, --NR.sup.2 R.sup.3 and --OR.sup.2 in which R.sup.2 and R.sup.3 are each independently H, C.sub.1-4 -alkyl or phenyl;
- X is halogen or H;
- a is an integer selected from 8, 12 and 16;
- b is an integer from 0 to 15;
- a+b is equal to 16;
- except for the compounds:
- ClAlPc(2-naphthyl-O).sub.8 H.sub.8,
- Li.sub.2 pc(2-naphthyl-O).sub.8 H.sub.8,
- ClGaPc(Ph--O).sub.8 H.sub.8,
- ClGaPc(Ph--O).sub.8 Cl.sub.8,
- ClAlPc(2-naphthyl-O).sub.8 Cl.sub.8
- ClGaPc(Ph--O).sub.16
- CllnPc(2-naphthyl-).sub.16.
16 more elements
A compound of the Formula (3):
- M.sub.k Pc(O--R.sup.1).sub.a X.sub.b Formula ( 3)
- wherein:
- M.sub.k Pc is as defined in Formula (1):
- ##STR7## wherein:
- M is selected from the group consisting of Zn, ClAl, OHAl, ClRh, OHRh, Clln, Brln, OHln, OHGa, Pt, Pd, Li, Na, K, Ca, Ba, Mg, ClSc and OHSc;
- k is the inverse of 1/2 of the valency of M.sub.k ;
- R.sup.1 is selected from the group consisting of phenyl, naphthyl, pyridyl, thiophenyl, furanyl, quinolinyl, thiazolyl, benzothiazolyl, pyrimidyl, each of which independently is unsubstituted or substituted by a substituent selected from the group consisting of C.sub.1-20 -alkyl, C.sub.1-20 -alkoxy, C.sub.2-20 -alkenyl, C.sub.1-20 -alkylthiol, C.sub.1-20 -alkoxycarbonyl, hydroxy C.sub.1-4 -alkoxy, phenyl, benzyl, phenylthio, fluoro, chloro, bromo, --CN, --NO.sub.2, --CF.sub.3, --COR.sup.2, --COOR.sup.2, --CONR.sup.2 R.sup.3, --SO.sub.2 R.sup.2, --SO.sub.2 NR.sup.2 R.sup.3, --NR.sup.2 R.sup.3 and --OR.sup.2 in which R.sup.2 and R.sup.3 are each independently H, C.sub.1-4 -alkyl or phenyl;
- X is halogen or H;
- a is an integer selected from 8, 12 and 16;
- b is an integer from 0 to 15;
- a+b is equal to 16;
- provided that when M is Clln, X is halogen;
- provided that when M is AlCl, a is 16;
- and provided that when M is Li, a is 12 or 16.
11 more elements
Dependencies are inferred from the claim text.