Provided herein are a reversibly reducible material and a method of forming a reversibly reducible material. The reversibly reducible material includes the molecular formula:

##STR00001##

wherein each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently selected from the group consisting of hydrogen, oxygen, alkyl, cycloalkyl, O-alkyl, amine, quaternary ammonium, and sulfonate; R.sup.5 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, and amine; X is selected from the group consisting of hydrogen, branched or un-branched alkyl chain having 1-8 atoms containing 0-3 oxygen or nitrogen atoms, and substituted or unsubstituted aryl; and Z is selected from the group consisting of branched or un-branched alkyl chain having 1-8 atoms containing 0-3 oxygen or nitrogen atoms, and substituted or unsubstituted aryl. The method of forming a reversibly reducible material comprising reacting a quinone with an amine in an ethereal solvent. Also provided herein is a negolyte.

A method for producing an arene with an aromatic CN bond ortho to an aromatic CO bond from a hydroxy arene comprising said aromatic CO bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a CN bond ortho to a CO bond of Formula (Va) and (Vb), respectively: ##STR00001##

A method for producing an arene with an aromatic CN bond ortho to an aromatic CO bond from a hydroxy arene comprising said aromatic CO bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a CN bond ortho to a CO bond of Formula (Va) and (Vb), respectively: ##STR00001##

A method for producing an arene with an aromatic CN bond ortho to an aromatic CO bond from a hydroxy arene comprising said aromatic CO bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a CN bond ortho to a CO bond of Formula (Va) and (Vb), respectively:

##STR00001##

A method for producing an arene with an aromatic CN bond ortho to an aromatic CO bond from a hydroxy arene comprising said aromatic CO bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a CN bond ortho to a CO bond of Formula (Va) and (Vb), respectively:

##STR00001##

Methods for asymmetric cis-dihydroxylation (AD) of quinones to produce cis-diols of quinones with high yield (i.e. a yield 30%) and high enantioselectivity (i.e. an enantiometric excess 30%) are disclosed. The method uses an iron-based catalyst, such as one or more Fe(II) complexes, as the catalyst, and can be performed under mild reaction conditions (e.g. a temperature 50 C. at 1 atom in open air). The method generally includes: (i) maintaining a reaction mixture at a temperature for a period of time sufficient to form a product, where the reaction mixture contains a quinone, one or more iron-based catalyst(s), and a solvent, and where the product contains a chiral cis-diol. Optionally, the method also includes adding an oxidant into the reaction mixture prior to and/or during step (i), such as a hydrogen peroxide solution.

Methods for asymmetric cis-dihydroxylation (AD) of quinones to produce cis-diols of quinones with high yield (i.e. a yield 30%) and high enantioselectivity (i.e. an enantiometric excess 30%) are disclosed. The method uses an iron-based catalyst, such as one or more Fe(II) complexes, as the catalyst, and can be performed under mild reaction conditions (e.g. a temperature 50 C. at 1 atom in open air). The method generally includes: (i) maintaining a reaction mixture at a temperature for a period of time sufficient to form a product, where the reaction mixture contains a quinone, one or more iron-based catalyst(s), and a solvent, and where the product contains a chiral cis-diol. Optionally, the method also includes adding an oxidant into the reaction mixture prior to and/or during step (i), such as a hydrogen peroxide solution.

An electroactive species includes a quinone core structure and at least one stabilizing group covalently bound thereto. The stabilizing group includes a cationic group, a hydrogen bond donor, or a combination thereof. The electroactive species has an oxidized state and at least one reduced state capable of bonding with a Lewis acid gas to form an anion adduct. Methods for separating a Lewis acid gas from a fluid mixture, electrochemical cells, and gas separation systems are also provided.

An electroactive species includes a quinone core structure and at least one stabilizing group covalently bound thereto. The stabilizing group includes a cationic group, a hydrogen bond donor, or a combination thereof. The electroactive species has an oxidized state and at least one reduced state capable of bonding with a Lewis acid gas to form an anion adduct. Methods for separating a Lewis acid gas from a fluid mixture, electrochemical cells, and gas separation systems are also provided.