A Convenient Synthesis of Some Haloferrocenes

Fish, R. W.; Rosenblum, M.

doi:10.1021/jo01015a511

Cited by 138 publications

(59 citation statements)

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“…Subsequent reaction with N-iodosuccinimide gave the monofunctionalized iodoferrocene (3). [30] Ullmann coupling gave BFc (4). [31] Friedel-Craft acylation with succinic anhydride gave the monoacylated product 5 in moderate yields (32 %) and, subsequently, the carboxylic acid 5 was converted into the more reactive ester 6.…”

Section: Resultsmentioning

confidence: 99%

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Redox‐Controlled Interaction of Biferrocenyl‐Terminated Dendrimers with β‐Cyclodextrin Molecular Printboards

Nijhuis

Dolatowska

Ravoo

et al. 2006

Chemistry A European J

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This paper describes the synthesis and electrochemistry of biferrocenyl‐terminated dendrimers and their β‐cyclodextrin (β‐CD) inclusion complexes in aqueous solution and at surfaces. Three generations of poly(propylene imine) (PPI) dendrimers, decorated with 4, 8, and 16 biferrocenyl (BFc) units, respectively, were synthesized. A water‐soluble BFc derivative forms stable inclusion complexes with β‐CD. The intrinsic binding constant is Ki=2.5×104 M−1. The BFc dendrimers were solubilized in water by complexation of the end groups with β‐CD, resulting in large water‐soluble supramolecular assemblies. Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) showed that all the end groups are complexed to β‐CD. Adsorption of the dendrimers at self‐assembled monolayers (SAMs) of heptathioether‐functionalized β‐CD on gold (“molecular printboards”) resulted in stable monolayers of the dendrimers due to the formation of multivalent host–guest interactions between the BFc end groups of the dendrimers and the immobilized β‐CD molecules. The number of interacting end groups is 3, 4, and 4 for dendrimer generations 1, 2, and 3, respectively. The complexation of BFc to β‐CD is sensitive to the oxidation state of the BFc unit. Oxidation of neutral BFc‐Fe2(II,II) to the cationic, mixed‐valence biferrocenium BFc‐Fe2(II,III)+ resulted in dissociation of the host–guest complexes. Scan‐rate‐dependent CV and DPV analyses of the dendrimer–β‐CD assemblies immobilized at the β‐CD host surface and in solution revealed that the dendrimers are oxidized in three steps. First, the surface‐β‐CD‐bound BFc moieties are oxidized to the mixed‐valence state, Fe2(II,III)+, followed by the oxidation of the non‐surface‐interacting BFc groups to the Fe2(II,III)+ state. The third step involves the oxidation of all the BFc moieties to the Fe2(III,III)2+ state.

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Section: Resultsmentioning

confidence: 99%

“…Column chromatography was performed using silica gel (E. Merck, 0.040-0.063 mm, 230-240 mesh). Chloromercurioferrocene, [30] iodoferrocene, [30] and biferrocene [31] were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Redox‐Controlled Interaction of Biferrocenyl‐Terminated Dendrimers with β‐Cyclodextrin Molecular Printboards

Nijhuis

Dolatowska

Ravoo

et al. 2006

Chemistry A European J

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“…Bis(ferrocenyl)mercury was prepared according to the method in the report [18,19]. Firstly, a 250 mL, round-bottom flask was charged with thiophene (1.68 g) and 70 mL mixture solution of HOAC/H 2 O/H 2 SO 4 (90:7:3, v/v/v), the reaction mixture was stirred for 20 min.…”

Section: Preparation Of 25-diferrocenylthiophenementioning

confidence: 99%

Rapid-scan time-resolved FT-IR spectroelectrochemistry – Study on the electron transfer of ferrocene-substituted thiophenes

Jin

Tao

Liu

2008

Journal of Electroanalytical Chemistry

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“…Bromoferrocene 1, was obtained by the bromination of chloromercuriferrocene with N -bromosuccinimide [12]. The synthesis of chloromercuriferrocene was achieved through metallation of ferrocene with mercury(II) acetate followed by addition of lithium chloride [13].…”

Section: Monosubstituted Ferrocenylpyridine Ligandsmentioning

confidence: 99%

Synthesis, characterization and cytotoxicity of some palladium(II), platinum(II), rhodium(I) and iridium(I) complexes of ferrocenylpyridine and related ligands. Crystal and molecular structure of trans-dichlorobis(3-ferrocenylpyridine)palladium(II)

Rajput

Moss

Hutton

et al. 2004

Journal of Organometallic Chemistry

104

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A Convenient Synthesis of Some Haloferrocenes

Cited by 138 publications

References 1 publication

Redox‐Controlled Interaction of Biferrocenyl‐Terminated Dendrimers with β‐Cyclodextrin Molecular Printboards

Redox‐Controlled Interaction of Biferrocenyl‐Terminated Dendrimers with β‐Cyclodextrin Molecular Printboards

Rapid-scan time-resolved FT-IR spectroelectrochemistry – Study on the electron transfer of ferrocene-substituted thiophenes

Synthesis, characterization and cytotoxicity of some palladium(II), platinum(II), rhodium(I) and iridium(I) complexes of ferrocenylpyridine and related ligands. Crystal and molecular structure of trans-dichlorobis(3-ferrocenylpyridine)palladium(II)

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