Phosphorous-Based Sensors For Detection Of Multiple Solvents

Abstract

Embodiments of the present disclosure pertain to methods of monitoring an environment for the presence of a solvent by: (i) exposing the environment to a luminescent compound, where the relative luminescence emission intensity of the luminescent compound changes upon interaction with the solvent; and (ii) monitoring a change in the relative luminescence emission intensity of the luminescent compound, where the absence of the change indicates the absence of the solvent from the environment, and where the presence of the change indicates the presence of the solvent in the environment. The luminescent compounds include a phosphorous atom with one or more carboxyl groups, where the carboxyl groups are coordinated with one or more metallic ions (e.g., lanthanide ions and yttrium ions). The present disclosure also pertains to sensors for monitoring an environment for the presence of a solvent, where the sensors include one or more of the aforementioned luminescent compounds.

What is claimed is: 
     
         1 . A sensor for monitoring an environment for the presence of a solvent, wherein the sensor comprises:
 a luminescent compound represented by formula (8):   
       
         
           
           
               
               
           
         
         wherein the carboxyl groups are coordinated with a plurality of different metallic ions, 
         wherein each of M 1 , M 2  and M 3  comprises metallic ions selected from the group consisting of La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Y, and combinations thereof; 
         wherein each of R 1 , R 2 , and R 3  is independently selected from the group consisting of conjugated groups, aromatic groups, benzene groups, phenyl groups, aryl groups, heterocycles, cyclic groups, and combinations thereof; 
         wherein R 4  is selected from NR 7  or CR 8 R 9 ; and 
         wherein R 7 , R 8 , and R 9  are each independently selected from the group consisting of light absorbing groups, hydrogen, nitrogen groups, aliphatic groups, conjugated groups, aromatic groups, phenyl groups, aryl groups, heterocycles, cyclic groups, alkyl groups, alkenyl groups, alkynyl groups, halides, and combinations thereof, 
         wherein the relative luminescence emission intensity of the luminescent compound changes upon interaction with the solvent. 
       
     
     
         2 . The sensor of  claim 1 , wherein the sensor comprises a plurality of different luminescent compounds. 
     
     
         3 . The sensor of  claim 2 , wherein the plurality of different luminescent compounds is capable of monitoring the presence of one or more solvents in the environment. 
     
     
         4 . The sensor of  claim 1 , wherein the luminescent compound is porous. 
     
     
         5 . The sensor of  claim 1 , wherein the luminescent compound is in the form of a crystalline lattice. 
     
     
         6 . The sensor of  claim 5 , wherein the metallic ions in the luminescent compound coordinate with carboxyl groups on adjacent luminescent compounds to form the crystalline lattice. 
     
     
         7 . The sensor of  claim 1 , wherein the one or more metallic ions comprise lanthanide ions selected from the group consisting of Tb, Eu, Gd, and combinations thereof. 
     
     
         8 . The sensor of  claim 1 , wherein the phosphorous atom in the luminescent compound is oxidized. 
     
     
         9 . The sensor of  claim 1 , wherein each of M 1 , M 2  and M 3  comprises lanthanide ions selected from the group consisting of Tb, Eu, Gd, and combinations thereof. 
     
     
         10 . The sensor of  claim 1 , wherein each of R 1 , R 2  and R 3  comprises a phenyl group. 
     
     
         11 . A sensor for monitoring an environment for the presence of a solvent, wherein the sensor comprises:
 a luminescent compound represented by formula (8):   
       
         
           
           
               
               
           
         
         wherein the carboxyl groups are coordinated with metallic ions, 
         wherein each of M 1 , M 2  and M 3  comprises metallic ions selected from the group consisting of La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Y, and combinations thereof; 
         wherein each of R 1 , R 2 , and R 3  is independently selected from the group consisting of conjugated groups, aromatic groups, benzene groups, phenyl groups, aryl groups, heterocycles, cyclic groups, and combinations thereof; 
         wherein R 4  is selected from NR 7  or CR 8 R 9 ; and 
         wherein R 7 , R 8 , and R 9  are each independently selected from the group consisting of light absorbing groups, hydrogen, nitrogen groups, aliphatic groups, conjugated groups, aromatic groups, phenyl groups, aryl groups, heterocycles, cyclic groups, alkyl groups, alkenyl groups, alkynyl groups, halides, and combinations thereof, 
         wherein the relative luminescence emission intensity of the luminescent compound changes upon interaction with the solvent. 
       
     
     
         12 . The sensor of  claim 11 , wherein the sensor comprises a single luminescent compound. 
     
     
         13 . The sensor of  claim 12 , wherein the single luminescent compound is capable of monitoring the presence of a plurality of different solvents in the environment. 
     
     
         14 . The sensor of  claim 11 , wherein the luminescent compound comprises a single metallic ion. 
     
     
         15 . The sensor of  claim 11 , wherein the luminescent compound comprises a plurality of the same metallic ions. 
     
     
         16 . A method of monitoring an environment for the presence of a solvent, wherein the method comprises:
 (i) exposing the environment to a luminescent compound,
 wherein the luminescent compound is represented by formula (8): 
   
       
         
           
           
               
               
           
         
         wherein the carboxyl groups are coordinated with a plurality of different metallic ions, 
         wherein each of M 1 , M 2  and M 3  comprises metallic ions selected from the group consisting of La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Y, and combinations thereof; 
         wherein each of R 1 , R 2 , and R 3  is independently selected from the group consisting of conjugated groups, aromatic groups, benzene groups, phenyl groups, aryl groups, heterocycles, cyclic groups, and combinations thereof; 
         wherein R 4  is selected from NR 7  or CR 8 R 9 ; and 
         wherein R 7 , R 8 , and R 9  are each independently selected from the group consisting of light absorbing groups, hydrogen, nitrogen groups, aliphatic groups, conjugated groups, aromatic groups, phenyl groups, aryl groups, heterocycles, cyclic groups, alkyl groups, alkenyl groups, alkynyl groups, halides, and combinations thereof, 
         wherein the relative luminescence emission intensity of the luminescent compound changes upon interaction with the solvent; and 
         (ii) monitoring a change in the relative luminescence emission intensity of the luminescent compound, and 
         wherein the presence of the change indicates the presence of the solvent in the environment. 
       
     
     
         17 . The method of  claim 16 , wherein the environment is selected from the group consisting of a liquid environment, a solid environment, a gaseous environment, and combinations thereof. 
     
     
         18 . The method of  claim 16 , wherein the environment is a liquid environment selected from the group consisting of reservoirs, water formations, solutions, solvent feed stocks, and combinations thereof; or the environment include air, a landfill, a single solvent, or a plurality of different solvents. 
     
     
         19 . The method of  claim 16 , wherein the solvent is selected from the group consisting of water, alcohols, dioxane, toluene, dimethyl formamide, hexanes, chloroform, acetonitrile, pyridine, deuterium oxide, and combinations thereof. 
     
     
         20 . The method of  claim 16 , wherein the exposing occurs by a method selected from the group consisting of mixing, incubating, swapping, dipping, and combinations thereof. 
     
     
         21 . The method of  claim 16 , wherein the change in the relative luminescence emission intensity of the luminescent compound is reversible; or wherein the change in the relative luminescence emission intensity of the luminescent compound is represented by a change in color.