Christine M. Thomas, O. Rüdiger, T. Liu
Jul 4, 2007
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Organometallics
Abstract
Model complexes of [FeFe]-hydrogenase bearing carboxylic acid functionalities have been designed for applications toward immobilization of hydrogen production electrocatalysts on amino-functionalized carbon electrode surfaces. Using carboxylic acid-substituted thiols, complexes incorporating the −COOH moiety into the thiolate linkers have been synthesized: (μ-SCH2CH2COOH)2[Fe(CO)3]2 (1) and the previously known (μ-(SCH2)2CHCOOH)[Fe(CO)3]2 (2). Carboxylic acid units have also been introduced via ligand substitution with a tricarboxyethyl phosphine to generate (μ-pdt)[Fe(CO)3][Fe(CO)2{P(C2H4COOH)3}] (3). To mimic the linkage of complexes of these types to amino-functionalized monolayers, it has been demonstrated that 2 can be coupled with aniline in solution to generate (μ-(SCH2)2CHCONHPh)[Fe(CO)3]2 (4), and the stability of this linkage has been addressed. The carboxylic acid-substituted complex 2 undergoes ligand substitution with PMe3 to generate (μ-(SCH2)2CHCOOH)[Fe(CO)2(PMe3)]2 (5). Complex 5 can then...