“…The maleamic acid is a nitrogen-containing analog of maleic acid. The N-substituted maleamic acids are highly conjugated, and their use as polydentate ligands has been well documented with lanthanide ions such as La 3+ [11], Eu 3+ , Tb 3+ and Yb 3+ [12], and transition metals such as Cu 2+ [13,14]. The most common method for the maleamic acid synthesis involves the reaction between a primary amine and maleic anhydride under mild reaction conditions (Scheme 1), in a wide variety of solvents, for instance, dichloromethane [15], diethyl ether [16], toluene [17], tetrahydrofuran [18] or xylene [19], which may pose health and environmental hazards.…”
We herein report the synthesis and characterization of six α,β-unsaturated dicarboxylic acid ligands with different phenyl spacers, and two ligands with a biphenyl and anthraquinone spacers. All these dimaleamic acids were synthesized in 16 to 99% yields via a base-catalyzed maleimide ring opening in water (ligand 2), or by a di-N-acylation from the corresponding diamines and maleic anhydride in acetic acid (ligands 4, 6, 8, 10, 12, 14 and 16). These reactions were performed using green solvents, while requiring minimal work up procedures, making them suitable alternatives to access these types of bidentate ligands quickly, which can be used to fabricate new metal-organic frameworks (MOFs).
“…The maleamic acid is a nitrogen-containing analog of maleic acid. The N-substituted maleamic acids are highly conjugated, and their use as polydentate ligands has been well documented with lanthanide ions such as La 3+ [11], Eu 3+ , Tb 3+ and Yb 3+ [12], and transition metals such as Cu 2+ [13,14]. The most common method for the maleamic acid synthesis involves the reaction between a primary amine and maleic anhydride under mild reaction conditions (Scheme 1), in a wide variety of solvents, for instance, dichloromethane [15], diethyl ether [16], toluene [17], tetrahydrofuran [18] or xylene [19], which may pose health and environmental hazards.…”
We herein report the synthesis and characterization of six α,β-unsaturated dicarboxylic acid ligands with different phenyl spacers, and two ligands with a biphenyl and anthraquinone spacers. All these dimaleamic acids were synthesized in 16 to 99% yields via a base-catalyzed maleimide ring opening in water (ligand 2), or by a di-N-acylation from the corresponding diamines and maleic anhydride in acetic acid (ligands 4, 6, 8, 10, 12, 14 and 16). These reactions were performed using green solvents, while requiring minimal work up procedures, making them suitable alternatives to access these types of bidentate ligands quickly, which can be used to fabricate new metal-organic frameworks (MOFs).
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