US 11,142,835 B2 · Compounds, their preparation, related compositions, catalysts, electrochemical cells, fuel cells, and uses thereof

Abstract

In some embodiments, this application relates to inventive compounds (e.g., Formula (I), Formula (II), thiosemicarbazones and/or thiosemicarbazones and their metal (e.g., zinc, cobalt, nickel, or copper) complexes, and extended structures thereof), methods for preparation of the inventive compounds, compositions comprising the inventive compounds (e.g., anode, cathodes, catalysts (e.g., electrocatalysts), glassy carbon electrodes, carbon paste electrodes, covalently modified carbon (e.g., modified graphene)), electrochemical cells comprising compositions that comprise one or more inventive compounds, fuel cells comprising compositions that comprise one or more inventive compounds, uses of one or more inventive compounds to produce H2 (e.g., via an electrochemical cell), and uses of one or more inventive compounds to create energy from H2 (e.g., via a fuel cell). Additional embodiments of the invention are also discussed herein.

A catalyst comprising a composition comprising a compound selected from Formula (I),

and
salts, optical isomers, geometric isomers, salts of isomers, and derivatives thereof, wherein
R1 is
or is a monovalent H, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), sulfo (—SO3H), halogen, aryl, cycloalkyl, heterocyclyl, heteroaryl, C1—C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy, which aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
X1 is bivalent —(NH)—, —O—, —(CH2)—, or —S—, which —(NH)— or —(CH2)— can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
R2 is a monovalent H, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), sulfo (—SO3H), halogen, aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy, which aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, amine (—NH2), —NRaRb, —N(+)RaRbRc, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
R3 is a monovalent H, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), sulfo (—SO3H), halogen, aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy, which aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
R4 is a monovalent H, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), sulfo (—SO3H), halogen, aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy, which aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
R5 is
or is a monovalent H, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), sulfo (—SO3H), halogen, aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy, which aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
X2 is bivalent —(NH)—, —O—, —(CH2)—, or —S—, which —(NH)— or —(CH2)— can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
R6 is a monovalent H, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), sulfo (—SO3H), halogen, aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy, which aryl, cycloalkyl, heterocyclyl, heteroaryl, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C1-C6 alkoxy can optionally be substituted with one or more of halogen, hydroxy (—OH), C1-C5 alkyl, C1-C4 alkoxy, amine (—NH2), —NRaRb, —N(+)RaRbRc, methanoly (—COH), carboxy (—CO2H), nitro (—NO2), cyano (—CN), ethynyl (—CCH), sulfo (—SO3H), methyl, or ethyl;
Ra, Rb, and Rc are each independently selected from C1-C5 alkyl;
and
the compound is not

12 more elements

Compounds, their preparation, related compositions, catalysts, electrochemical cells, fuel cells, and uses thereof

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Compounds, their preparation, related compositions, catalysts, electrochemical cells, fuel cells, and uses thereof

Life of this patent

Abstract

Claims29