Synthesis of poly-(p-aryleneethynylene)s in neat water under aerobic condit

Abstract

Provided are ethyne synthons comprising boron and related methods. Also provided are related water-soluble arylethynylene polymers capable of being synthesized in neat water under aerobic conditions.

1 . An oligomer or polymer, comprising:
 a plurality of aryleneethynylene units composed of arylene units covalently bonded to ethynylene units,   each of the arylene units comprising at least one water solubilizing group.   
   
   
       2 . The oligomer or polymer of  claim 1 , wherein the oligomer or polymer comprises a block copolymer, a multi-block polymer, a copolymer, or any combination or portion thereof. 
   
   
       3 . The oligomer or polymer of  claim 1 , wherein at least one arylene unit comprises ten or fewer fused aromatic ring systems. 
   
   
       4 . (canceled) 
   
   
       5 . The oligomer or polymer of  claim 1 , wherein at least one water solubilizing group comprises a saccharide-, a disaccharide-, a polysaccharide-, a nucleoside-, a dinucleoside-, an oligonucleoside-, a deoxynucleoside-, a dideoxynucleoside-, an oligodeoxynucleoside-, a nucleotide-, a dinucleotide-, an oligonucleotide-, a deoxynucleotide-, a dideoxynucleotide-, an oligodeoxynucleotide-, a peptide-, a dipeptide-, an oligopeptide-, a glycol-, a poly(ethylene oxide)-, a poly(ethylene glycol)-group, or any combination thereof. 
   
   
       6 . The oligomer or polymer of  claim 1 , wherein at least one of the water-solubilizing groups comprises an acid, a salt, or any combination thereof. 
   
   
       7 . The oligomer or polymer of  claim 1 , wherein at least one of the water-solubilizing groups is capable of being at least partially ionized in water. 
   
   
       8 - 13 . (canceled) 
   
   
       14 . The oligomer or polymer of  claim 5 , wherein the alkoxy sulfonic acid comprises 3-propoxysulfonic acid. 
   
   
       15 . (canceled) 
   
   
       16 . The oligomer or polymer of  claim 5 , wherein at least one water-solubilizing group comprises NH 3   + , NH 2 R + , NHR 2   + , NR 3   + , immidazolium, pyridinium, N-alkylpyridinium, bipyridinium, (CH 2 ) n —CO—NR 2 , or any combination thereof, wherein n is in the range of from 2 to 8, and wherein R comprises a hydrogen, an alkyl, an aryl, a heterocycle, or any combination thereof. 
   
   
       17 . An oligomer or polymer, comprising:
 a plurality of [aromatic heterocycle]ethynylene units composed of aromatic heterocycle units covalently bonded to ethynylene units, wherein each the aromatic heterocycle units comprises at least one water solubilizing functional group.   
   
   
       18 . The oligomer or polymer of  claim 17 , wherein at least one of the aromatic heterocycle units comprises from about 4 to about 20 carbon atoms. 
   
   
       19 . (canceled) 
   
   
       20 . The oligomer or polymer of  claim 17 , wherein at least one water solubilizing group comprises a saccharide-, a disaccharide-, a polysaccharide-, a nucleoside-, a dinucleoside-, an oligonucleoside-, a deoxynucleoside-, a dideoxynucleoside-, an oligodeoxynucleoside-, a nucleotide-, a dinucleotide-, an oligonucleotide-, a deoxynucleotide-, a dideoxynucleotide-, an oligodeoxynucleotide-, a peptide-, a dipeptide-, an oligopeptide-, a glycol-, a poly(ethylene oxide)-, a poly(ethylene glycol)-group, or any combination thereof. 
   
   
       21 . The oligomer or polymer of  claim 17 , wherein at least one of the water-solubilizing groups comprises an acid, a salt, or any combination thereof. 
   
   
       22 - 26 . (canceled) 
   
   
       27 . The oligomer or polymer of  claim 20 , wherein the alkoxy sulfonic acid comprises 3-propoxysulfonic acid. 
   
   
       28 . (canceled) 
   
   
       29 . The oligomer or polymer of  claim 20 , wherein a water-solubilizing group comprises NH 3   + , NH 2 R + , NHR 2   + , NR 3   + , immidazolium, pyridinium, N-alkylpyridinium, bipyridinium, (CH 2 ) n —CO—NR 2 , or any combination thereof, wherein n is in the range of from 2 to 8, and wherein R comprises a hydrogen, an alkyl, an aryl, a heterocycle, or any combination thereof. 
   
   
       30 . An oligomer or polymer, comprising:
 a plurality of [conjugated macrocycle]ethynylene units composed of a conjugated macrocycle group covalently bonded to an ethynylene group, and
 each of the conjugated macrocycle groups comprising at least one water solubilizing functional group. 
   
   
   
       31 . The oligomer or polymer of  claim 30 , wherein at least one of the conjugated macrocyclic groups comprises a porphyrin-, an N-confused porphyrin, a porphycene-, a rubyrin-, a rosarin-, a hexaphyrin-, a sapphyrin-, a chlorophyll-, a chlorin-, a phthalocynine-, a porphyrazine-, a bacteriochlorophyl-, a pheophytin-, or texaphyrin-based component-, or a metalated derivative thereof, or any combination thereof. 
   
   
       32 . The oligomer or polymer of  claim 30 , wherein at least one water solubilizing group comprises a saccharide-, a disaccharide-, a polysaccharide-, a nucleoside-, a dinucleoside-, an oligonucleoside-, a deoxynucleoside-, a dideoxynucleoside-, an oligodeoxynucleoside-, a nucleotide-, a dinucleotide-, an oligonucleotide-, a deoxynucleotide-, a dideoxynucleotide-, an oligodeoxynucleotide-, a peptide-, a dipeptide-, an oligopeptide-, a glycol-, a poly(ethylene oxide)-, a poly(ethylene glycol)-group, or any combination thereof. 
   
   
       33 - 123 . (canceled)