PEG-Substituted Pyridine Ligands and Related Water-Soluble Catalysts

Abstract

Amphiphilic Group VIII metathesis catalysts, as can be used in a range of polymerization reactions and other chemical methodologies.

1 . A Group VIII transition metal compound of a formula 
       
         
           
           
               
               
           
         
       
       wherein M is a metal selected from a Group VIII transition metal; X 1  and X 2  are independently selected from anionic ligand components; L 1 -L 3  are independently selected from neutral electron donor ligand components, providing one of said L 1 -L 3  components is an N-heterocyclic carbene component and the other said L 1 -L 3  components are independently selected from amphiphilic substituted pyridinyl ligand components, said amphiphilic substituent comprising at least one of an alkoxy moiety and an alkoxycarbonyl moiety; and R 1 -R 2  are independently selected from hydrogen, alkyl, substituted alkyl, cyclic alkyl, substituted cyclic alkyl, alkenyl, substituted alkenyl, cyclic alkenyl, substituted cyclic alkenyl, phenyl and substituted phenyl moieties. 
     
     
         2 . The compound of  claim 1  wherein at least one of said pyridinyl ligand components comprises a polyalkoxy substituent. 
     
     
         3 . The compound of  claim 2  wherein said substituent comprises (OCH 2 CH 2 ) n , and n ranges from about 2 to about 100. 
     
     
         4 . The compound of  claim 1  wherein M is selected from Ru and Os. 
     
     
         5 . The compound of  claim 4  wherein R 1  is hydrogen and R 2  is phenyl. 
     
     
         6 . A metathesis catalyst compound of a formula 
       
         
           
           
               
               
           
         
       
       wherein X 1  and X 2  are independently selected from anionic ligand components; L 1 -L 3  are independently selected from neutral electron donor ligand components, providing one of said L 1 -L 3  components is an N-heterocyclic carbene component and the other said L 1 -L 3  components are independently selected from amphiphilic substituted pyridinyl ligand components, said amphiphilic substituent comprising at least one of an alkoxy moiety and an alkoxycarbonyl moiety; and R 1 -R 2  are independently selected from hydrogen, alkyl, substituted alkyl, cyclic alkyl, substituted cyclic alkyl, alkenyl, substituted alkenyl, cyclic alkenyl, substituted cyclic alkenyl, phenyl and substituted phenyl moieties. 
     
     
         7 . The compound of  claim 6  wherein at least one of said pyridinyl ligand components comprises a polyalkoxy substituent. 
     
     
         8 . The compound of  claim 7  wherein said substituent comprises (OCH 2 CH 2 ) n , and n ranges from about 2 to about 100. 
     
     
         9 . The compound of  claim 6  wherein said carbene ligand component comprises a 4,5-dihydroimidazolylidene moiety. 
     
     
         10 . The compound of  claim 9  wherein R 1  is hydrogen and R 2  is phenyl. 
     
     
         11 . A reaction system comprising an amphiphilic compound of  claim 6  and at least one alkene compound. 
     
     
         12 . The system of  claim 11  comprising two acyclic alkene compounds, said system for a cross-metathesis reaction. 
     
     
         13 . The system of  claim 12  comprising a cyclic alkene compound and an acyclic alkene compound, said system for a ring-opening cross-metathesis reaction. 
     
     
         14 . The system of  claim 11  comprising a cyclic alkene compound, said system for a ring-opening metathesis polymerization reaction. 
     
     
         15 . The system of  claim 14  wherein said alkene compound is coupled to a substrate. 
     
     
         16 . The system of  claim 15  wherein said substrate is a nanodimensioned particulate. 
     
     
         17 . The system of  claim 15  wherein said alkene compound is cross-linked with another said alkene compound coupled to said substrate. 
     
     
         18 . The system of  claim 17  wherein said nanodimensional particulate comprises a semiconductive, luminescent material.