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US 5,756,723 AGranted
Metal-mediated cross-coupling with ring-metalated porphyrins
AssigneeThe Trustees of the University of Pennsylvania
InventorsMichael J. Therien, Stephen G. DiMagno
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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 anionic groups via metal-mediated cross-coupling reactions under stoichiometric or catalytic conditions.
Claims12
A process for preparing a substituting porphyrin, comprising the steps of:
- providing a porphyrin compound having formula (1) or (2):
- ##STR7## 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 is a first halogen;
- contacting said porphyrin compound with a complex having formula Y(L).sub.2 wherein Y is a first metal and L is a ligand, said contacting being performed under conditions effective to produce a first reaction product;
- contacting said first reaction product with an organometallic compound having formula T(R.sub.L).sub.z (R.sub.O), T(R.sub.L).sub.z (R.sub.O).sub.t (X.sub.B).sub.w, T(R.sub.O) (X.sub.B) or T(R.sub.O).sub.t where:
- T is a second metal;
- X.sub.B is a second halogen or an alkoxy group;
- R.sub.L is cyclopentadienyl or aryl having about 6 to about 20 carbon atoms;
- R.sub.O is alkyl, alkenyl or alkynyl having 1 to about 10 carbon atoms, aryl having about 6 to about 20 carbon atoms;
- and
- z and w are greater than or equal to 0 and t is at least 1;
- said contacting being performed under conditions effective to produce a second reaction product comprising a substituted porphyrin having formula (1) or (2) wherein at least one of at least one of R.sub.A1 -R.sub.A4 or R.sub.B1 -R.sub.B8 is R.sub.O.
8 more elements
A process for derivatizing a porphyrin compound, comprising the steps of:
- providing a porphyrin compound having formula (2):
- ##STR8## wherein at least one of R.sub.A1 -R.sub.A4 or R.sub.B1 -R.sub.B8 is a first halogen;
- and M is chelated metal atom;
- and
- contacting said porphyrin compound with a complex having formula Y(L).sub.2 where Y is a metal and L is a ligand, said contacting being performed under conditions effective to produce a first reaction product that includes a compound having formula P.sub.N -Y(L).sub.2 X.sub.A wherein P.sub.N is said porphyrin compound and X.sub.A is said first halogen.
2 more elements
Dependencies are inferred from the claim text.