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US 5,371,199 AGranted
Substituted porphyrins, porphyrin-containing polymers, and synthetic methods therefor
AssigneeThe Trustees of the University of Pennsylvania
InventorsMichael J. Therien, Stephen G. DiMagno
Life of this patent
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Abstract
Porphyrins substituted with, for example, vinyl and acetylene groups are provided, along with polymers containing the same. In preferred embodiments, the substituted porphyrins are prepared by coupling halogenated porphyrins with carbon-centered anionic groups via metal-mediated crosscoupling reactions under stoichiometric or catalytic conditions.
Claims44
A compound having formula (1) or (2):
- ##STR7## wherein:
- (a) at least two of R.sub.A1 -R.sub.A4 has formula CH.dbd.CH.sub.2 ;
- or
- (b) at least one of R.sub.B1 -R.sub.B8 has formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E), provided that at least one of R.sub.C, R.sub.D, and R.sub.E is not H;
- or
- (c) at least two of R.sub.B1 -R.sub.B8 have formula C.dbd.C(R.sub.D);
- or
- (d) at least one of R.sub.A1 -R.sub.A4 is haloalkyl having 1 to about 20 carbon atoms;
- or
- (e) at least one of R.sub.B1 -R.sub.B8 is haloalkyl having 2 to about 20 carbon atoms;
- or
- (f) at least five of R.sub.B1 -R.sub.B8 are haloalkyl having 1 to about 20 carbon atoms or haloaryl having about 6 to about 20 carbon atoms;
- or
- (h) at least one of R.sub.A1 -R.sub.A4 has formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E), provided that at least two of R.sub.C, R.sub.D and R.sub.E are not H;
- or
- (i) at least two of R.sub.A1 -R.sub.A4 have formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E), provided that at least one of R.sub.C, R.sub.D, and R.sub.E is not H;
- where R.sub.C, R.sub.D, and R.sub.E are, independently, H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinatol;
- and
- M is a chelated metal atom.
16 more elements
A compound having formula (1) or (2):
- ##STR8## wherein:
- at least one of R.sub.A1 -R.sub.A4 or R.sub.B1 -R.sub.B8 is a halogen;
- and
- at least one of the remaining R.sub.A1 -R.sub.A4 or R.sub.B1 -R.sub.B8 is C(R.sub.C).dbd.C(R.sub.D)(R.sub.E), C.dbd.C(R.sub.D), haloalkyl having from 1 to about 20 carbon atoms, or haloaryl having about 6 to about 20 carbon atoms where R.sub.C, R.sub.D, and R.sub.E are, independently, H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato;
- and
- M is a chelated metal atom.
3 more elements
A compound having formula (1) or (2):
- ##STR9## wherein M is a chelated metal atom and at least one of R.sub.A1 -R.sub.A4 or R.sub.B1 -R.sub.B8 has formula Y(L).sub.2 X.sub.A where Y is a metal, L is a ligand, and X.sub.A is a halogen.
A compound having formula (1) or (2):
- ##STR10## wherein at least one of R.sub.A1 -R.sub.A4 or R.sub.B1 -R.sub.B8 has formula Y(L).sub.2 R.sub.O where M is a chelated metal atom, Y is a metal;
- L is a ligand;
- and R.sub.O is alkyl having 1 to about 10 carbon atoms, alkenyl or alkynyl having 2 to about 10 carbon atoms, aryl having bout 6 to about 20 carbon atoms.
A compound having formula (1) or (2):
- ##STR11## wherein:
- (a) R.sub.A1 has formula C.dbd.C(R.sub.D) provided that R.sub.D is not H or alkyl having 1 to about 20 carbon atoms;
- or
- (b) R.sub.A1 and R.sub.A2 have formula C.dbd.C(R.sub.D);
- or
- (c) R.sub.A1 and R.sub.A3 have formula C.dbd.C(R.sub.D) and R.sub.A2 and R.sub.A4 are not H;
- or
- (d) R.sub.A1, R.sub.A2, and R.sub.A3 have formula C.dbd.C(R.sub.D);
- or
- (e) R.sub.A1 -R.sub.A4 have formula C.dbd.C(R.sub.D) provided that R.sub.B1 -R.sub.B8 are not H or alkyl having 1 to about 20 carbon atoms;
- or
- (f) R.sub.A1 -R.sub.A4 have formula C.dbd.C(R.sub.D) provided that R.sub.D is not H or trialkylsilyl;
- where R.sub.D is H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato;
- and
- M is a chelated metal atom.
12 more elements
A compound having formula (1) or (2):
- ##STR12## wherein:
- (a) R.sub.A1 has formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E), provided that at least one of R.sub.C, R.sub.D, and R.sub.E is not H;
- or
- (b) R.sub.A1 and R.sub.A2 have formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E);
- or
- (c) R.sub.A1 and R.sub.A3 have formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E);
- or
- (d) R.sub.A1, R.sub.A2, and R.sub.A3 have formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E);
- or
- (e) R.sub.A1 -R.sub.A4 have has formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E), provided that at least one of R.sub.C, R.sub.D, and R.sub.E is not H and that R.sub.D and R.sub.E are not H, alkyl having from 1 to about 20 carbon atoms;
- or aryl having about 6 to about 20 carbon atoms;
- or
- (f) R.sub.A1 -R.sub.A4 have formula C(R.sub.C).dbd.C(R.sub.D)(R.sub.E), provided that at least one of R.sub.C, R.sub.D, and R.sub.E is not H and that at east two of R.sub.B1 -R.sub.B8 are not H;
- where R.sub.C, R.sub.D, and R.sub.E are, independently, H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato;
- and
- M is a chelated metal atom.
13 more elements
Dependencies are inferred from the claim text.