High Stability Diionic Liquid Salts

Abstract

The present invention relates to diionic liquid salts of dicationic or dianionic molecules, as well as solvents comprising diionic liquids and the use of diionic liquids as the stationary phase in a gas chromatographic column.

1 - 40 . (canceled) 
     
     
         41 . A diionic liquid salt comprising at least one dication of the formula
   A-B-A′
   and at least one counter anion, wherein
 A and A′ are optionally substituted imidazolium and at least one of A and A′ is substituted with a group that facilitates cross-linking and/or immobilization; and 
 B is an optionally substituted C 2 -C 40  hydrocarbon backbone, wherein the hydrocarbon backbone optionally contains, in addition to carbon and hydrogen atoms, at least one heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, and silicon. 
   
     
     
         42 . The diionic liquid salt of  claim 41 , wherein the diionic liquid salt has a solid/liquid transition temperature of about 100° C. or less. 
     
     
         43 . The diionic liquid salt of  claim 41 , wherein the diionic liquid salt has a solid/liquid transition temperature of about 25° C. or less. 
     
     
         44 . The diionic liquid salt of  claim 41 , wherein B has a length about equivalent to a C 3 -C 30  carbon chain. 
     
     
         45 . The diionic liquid salt of  claim 41 , wherein B is unsymmetric and contains a side chain group. 
     
     
         46 . The diionic liquid salt of  claim 41 , wherein B contains at least one unsaturated group which can facilitate cross-linking or immobilization. 
     
     
         47 . The diionic liquid salt of  claim 41 , wherein B contains at least one sulfur heteroatom. 
     
     
         48 . The diionic liquid salt of  claim 41 , wherein the at least one counter anion is a mono-ionic counter anion. 
     
     
         49 . The diionic liquid salt of  claim 48 , wherein the mono-ionic counter anion is independently selected from the group consisting of Br − , mono-sulfonate, mono-sulfate, NTf 2   − , BF 4   − , triflate and PF 6   − . 
     
     
         50 . The diionic liquid salt of  claim 41 , wherein the at least one counter anion is a diionic counter anion. 
     
     
         51 . The diionic liquid salt of  claim 50 , wherein the diionic counter anion is selected from the group consisting of dicarboxylate, disulfate and disulfonate. 
     
     
         52 . The diionic liquid salt of  claim 41 , wherein the dicationic species is selected from the group consisting of 
       
         
           
           
               
               
           
         
         wherein n is 3 to 30, inclusive. 
       
     
     
         53 . The diionic liquid salt of  claim 41 , wherein the dicationic species is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein n is 6, 9, 10, 11 or 12; and 
       
         
           
           
               
               
           
         
       
     
     
         54 . The diionic liquid salt of  claim 53 , wherein the at least one counter anion is NTf 2   − . 
     
     
         55 . The diionic liquid salt of  claim 41 , wherein the dicationic species is 
       
         
           
           
               
               
           
         
       
     
     
         56 . The diionic liquid salt of  claim 55 , wherein the at least one counter anion PF 6   − . 
     
     
         57 . A diionic liquid salt comprising at least one dication of the formula
   A-B-A′
   and at least one counter anion, wherein
 A and A′ are the same mono-cationic group selected from the group consisting of —[N(R) 2 H] + , —[As(R) 3 ] + , and tetrahydrothiophenium, wherein each R is independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and benzyl; and 
 B is an optionally substituted C 2 -C 40  hydrocarbon backbone, wherein the hydrocarbon backbone optionally contains, in addition to carbon and hydrogen atoms, at least one heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, and silicon. 
   
     
     
         58 . The diionic liquid salt of  claim 57 , wherein the diionic liquid salt has a solid/liquid transition temperature of about 100° C. or less. 
     
     
         59 . The diionic liquid salt of  claim 57 , wherein the diionic liquid salt has a solid/liquid transition temperature of about 25° C. or less. 
     
     
         60 . The diionic liquid salt of  claim 57 , wherein B has a length about equivalent to a C 3 -C 30  carbon chain. 
     
     
         61 . The diionic liquid salt of  claim 57 , wherein B is unsymmetric and contains a side chain group. 
     
     
         62 . The diionic liquid salt of  claim 57 , wherein B contains at least one unsaturated group which can facilitate cross-linking or immobilization. 
     
     
         63 . The diionic liquid salt of  claim 57 , wherein the at least one counter anion is a mono-ionic counter anion. 
     
     
         64 . The diionic liquid salt of  claim 63 , wherein the mono-ionic counter anion is independently selected from the group consisting of Br − , mono-sulfonate, mono-sulfate, NTf 2   − , BF 4   − , triflate and PF 6   − . 
     
     
         65 . The diionic liquid salt of  claim 57 , wherein the at least one counter anion is a diionic counter anion. 
     
     
         66 . The diionic liquid salt of  claim 65 , wherein the diionic counter anion is selected from the group consisting of dicarboxylate, disulfate and disulfonate 
     
     
         67 . The diionic liquid salt of  claim 57 , wherein the dicationic species is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein n is 2 to 40, inclusive.