Methods and intermediates for the synthesis of dipyrrin-substituted porphyrinic macrocycles

Abstract

The present invention provides dipyrrin substituted porphyrinic macrocycles, intermediates useful for making the same, and methods of making the same. Such compounds may be used for purposes including the making of molecular memory devices, solar cells and light harvesting arrays.

1 - 25 . (canceled) 
     
     
         26 . A method of synthesizing a trans-(dipyrrin) 2 -porphyrinic macrocycle, comprising:
 reacting a dipyrrin-carboxaldehyde with a dipyrromethane in the presence of an acid catalyst to produce said trans-(dipyrrin) 2 -porphyrinic macrocycle.   
     
     
         27 . The method of  claim 26 , wherein said reacting step is carried out at a temperature of from 0 to 100° C. 
     
     
         28 . The method of  claim 26 , wherein said reacting step is carried out in a solvent selected from the group consisting of dichloromethane, tetrahydrofuran, toluene, chloroform, and mixtures thereof. 
     
     
         29 . A porphyrinic macrocycle having from 1 to 4 dipyrrins substituted thereon. 
     
     
         30 . The porphyrinic macrocycle of  claim 29 , wherein said dipyrrins are substituted on said porphyrinic macrocycle at the meso or beta position. 
     
     
         31 . The porphyrinic macrocycle of  claim 29  having two dipyrrins trans substituted thereon. 
     
     
         32 . The porphyrinic macrocycle of  claim 29  coupled to a substrate. 
     
     
         33 . A polymer comprising a plurality of linked porphyrinic macrocycles, at least one of said porphyrinic macrocycles having from 1 to 4 dipyrrins substituted thereon. 
     
     
         34 . A polymer according to  claim 33  coupled to a substrate. 
     
     
         35 . A sandwich coordination compound of the formula L n M n-1 , where each L is an independently selected heterocyclic ligand, each M is a metal, n is 2 or 3, and at least one of said heterocyclic ligand is a porphyrinic macrocycles having from 1 to 4 dipyrrins substituted thereon. 
     
     
         36 . A sandwich coordination compound according to  claim 35  coupled to a substrate. 
     
     
         37 . An apparatus for storing data, said apparatus comprising a fixed electrode electrically coupled to a storage medium, said storage medium comprising a porphyrinic macrocycle having from 1 to 4 dipyrrins substituted thereon. 
     
     
         38 . A light harvesting array, comprising: (a) a first substrate comprising a first electrode; and (b) a layer of light harvesting rods electrically coupled to the first electrode, each of the light harvesting rods comprising a polymer of Formula I:
   X 1 X m+1 ) m   (I)
   
       wherein: m is at least 1; X 1  is a charge separation group having an excited-state of energy equal to or lower than that of X 2 ; X 2  through X m+1  are chromophores, and at least one of said chromophores comprises a porphyrinic macrocycle having from 1 to 4 dipyrrins substituted thereon.