Described herein are anionic phenylene oligomers and polymers, and devices including these materials. The oligomers and polymers can be prepared in a convenient and well-controlled manner, and can be used in cation exchange membranes. Also described is the controlled synthesis of anionic phenylene monomers and their use in synthesizing anionic oligomers and polymers, with precise control of the position and number of anionic groups.

An organic flow battery having a positive electrode electrolyte containing organic compounds with extended conjugation and/or cyclic side chains is provided. The flow battery includes a positive electrode and a positive electrode electrolyte including first solvent and a first redox couple. The positive electrode electrolyte flows over and contacting the positive electrode. The first redox couple includes a first organic compound and a reduction product of the first organic compound. The flow battery also includes a negative electrode and a negative electrode electrolyte including a second solvent and a second redox couple. The negative electrode electrolyte flows g over and contacts the positive electrode. Typically, an ion exchange membrane is interposed between the positive electrode and the negative electrode Characteristically, the first organic compound resists crossover through the ion exchange membrane.

An organic flow battery having a positive electrode electrolyte containing organic compounds with extended conjugation and/or cyclic side chains is provided. The flow battery includes a positive electrode and a positive electrode electrolyte including first solvent and a first redox couple. The positive electrode electrolyte flows over and contacting the positive electrode. The first redox couple includes a first organic compound and a reduction product of the first organic compound. The flow battery also includes a negative electrode and a negative electrode electrolyte including a second solvent and a second redox couple. The negative electrode electrolyte flows g over and contacts the positive electrode. Typically, an ion exchange membrane is interposed between the positive electrode and the negative electrode Characteristically, the first organic compound resists crossover through the ion exchange membrane.

An organic flow battery having a positive electrode electrolyte containing organic compounds with extended conjugation and/or cyclic side chains is provided. The flow battery includes a positive electrode and a positive electrode electrolyte including first solvent and a first redox couple. The positive electrode electrolyte flows over and contacting the positive electrode. The first redox couple includes a first organic compound and a reduction product of the first organic compound. The flow battery also includes a negative electrode and a negative electrode electrolyte including a second solvent and a second redox couple. The negative electrode electrolyte flows g over and contacts the positive electrode. Typically, an ion exchange membrane is interposed between the positive electrode and the negative electrode Characteristically, the first organic compound resists crossover through the ion exchange membrane.

An organic flow battery having a positive electrode electrolyte containing organic compounds with extended conjugation and/or cyclic side chains is provided. The flow battery includes a positive electrode and a positive electrode electrolyte including first solvent and a first redox couple. The positive electrode electrolyte flows over and contacting the positive electrode. The first redox couple includes a first organic compound and a reduction product of the first organic compound. The flow battery also includes a negative electrode and a negative electrode electrolyte including a second solvent and a second redox couple. The negative electrode electrolyte flows g over and contacts the positive electrode. Typically, an ion exchange membrane is interposed between the positive electrode and the negative electrode Characteristically, the first organic compound resists crossover through the ion exchange membrane.

Crystalline molecular framework:small molecule compounds. The molecular framework is formed from guanidinium cations and organosulfonate anions and the guanidinium cations and organosulfonate anions are associated via one or more hydrogen bond. The small molecule(s) is/are encapsulated by the molecular framework. Methods for making crystalline molecular framework:small molecule compounds may include combining guanidinium cations, organosulfonate anions, and small molecules in a single step. The crystalline molecular framework:small molecule compounds can be used to determine the structure of the small molecule(s).

Crystalline molecular framework:small molecule compounds. The molecular framework is formed from guanidinium cations and organosulfonate anions and the guanidinium cations and organosulfonate anions are associated via one or more hydrogen bond. The small molecule(s) is/are encapsulated by the molecular framework. Methods for making crystalline molecular framework:small molecule compounds may include combining guanidinium cations, organosulfonate anions, and small molecules in a single step. The crystalline molecular framework:small molecule compounds can be used to determine the structure of the small molecule(s).

Compositions comprising a sulfonated reaction product or a salt thereof may be prepared from a biphenyl compound that has been alkylated with an olefin of formula R.sup.1R.sup.2CCH.sub.2, wherein R.sup.1 is a C.sub.6-C.sub.24 hydrocarbyl group, and R.sup.2 is H or a C.sub.6-C.sub.24 hydrocarbyl group. Methods for sulfonating an alkylated biphenyl compound prepared from a biphenyl compound that has been alkylated with an olefin of formula R.sup.1R.sup.2CCH.sub.2, wherein R.sup.1 is a C.sub.6-C.sub.24 hydrocarbyl group, and R.sup.2 is H or a C.sub.6-C.sub.24 hydrocarbyl group may comprise contacting the alkylated biphenyl compound with a sulfonating reagent; forming a sulfonated reaction product; and converting the sulfonated reaction product into a sulfonate salt.

Compositions comprising a sulfonated reaction product or a salt thereof may be prepared from a biphenyl compound that has been alkylated with an olefin of formula R.sup.1R.sup.2CCH.sub.2, wherein R.sup.1 is a C.sub.6-C.sub.24 hydrocarbyl group, and R.sup.2 is H or a C.sub.6-C.sub.24 hydrocarbyl group. Methods for sulfonating an alkylated biphenyl compound prepared from a biphenyl compound that has been alkylated with an olefin of formula R.sup.1R.sup.2CCH.sub.2, wherein R.sup.1 is a C.sub.6-C.sub.24 hydrocarbyl group, and R.sup.2 is H or a C.sub.6-C.sub.24 hydrocarbyl group may comprise contacting the alkylated biphenyl compound with a sulfonating reagent; forming a sulfonated reaction product; and converting the sulfonated reaction product into a sulfonate salt.

Described herein are anionic phenylene oligomers and polymers, and devices including these materials. The oligomers and polymers can be prepared in a convenient and well-controlled manner, and can be used in cation exchange 5 membranes. Also described is the controlled synthesis of anionic phenylene monomers and their use in synthesizing anionic oligomers and polymers, with precise control of the position and number of anionic groups.