Dynamic behaviour of 1,n′-disubstituted ferrocenes

Heinze, Katja; Beckmann, Manuela

doi:10.1016/j.jorganchem.2006.08.096

Cited by 17 publications

(10 citation statements)

References 37 publications

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“…Organometallics, Vol. 28 support the interpretation that several conformers are required to adequately describe the properties of Fca-containing bisamides in solution.…”

Section: Bis-and Trisamidessupporting

confidence: 74%

Bis- and Trisamides Derived From 1′-Aminoferrocene-1-carboxylic Acid and α-Amino Acids: Synthesis and Conformational Analysis

et al. 2009

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Ferrocene derivatives with one or two achiral and chiral arms based on α-amino acids (Gly, l-Ala, l-Val) attached to the cyclopentadienyl rings were prepared by solution-phase peptide synthesis from N-acetyl- and N-Boc-protected 1′-aminoferrocene-1-carboxylic acids (Boc = tert-butoxycarbonyl). The conformational preference in the solid state of selected examples was elucidated by X-ray crystallography. The chiroptical properties of chiral bis- and trisamides were investigated by circular dichroism (CD) spectroscopy in solution. The conformational preference was studied by NMR and IR spectroscopy, as well as by molecular modeling (DFT). For the bisamides, a conformational library is observed in solution. Increasing the steric bulk of the amino acid side chain disfavors several energetically accessible conformers of bisamides and specific conformers can be selected by changing the environment (type of solvent; solid/solution). For the trisamides, a single conformer is highly stabilized by two intramolecular hydrogen bonds irrespective of the size of the protecting group, the size of the amino acid side chain and the medium.

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“…Organometallics, Vol. 28 support the interpretation that several conformers are required to adequately describe the properties of Fca-containing bisamides in solution.…”

Section: Bis-and Trisamidessupporting

confidence: 74%

Bis- and Trisamides Derived From 1′-Aminoferrocene-1-carboxylic Acid and α-Amino Acids: Synthesis and Conformational Analysis

et al. 2009

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“…[20] This functional/basis set combination has been successfully applied previously to investigate the conformational preference of substituted ferrocenes. [6,8,11,21,22] All points were characterised as minima (N imag = 0) by frequency analysis.…”

Section: Methodsmentioning

confidence: 99%

Solid‐Phase Synthesis of Chiral Modular Ferrocene‐Based Peptides

2007

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“…[22] The introduction of the ferrocene (Fc) group as a part of the peptide scaffold provides control over the secondary structure of the molecular precursor by promoting crossstrand hydrogen bonding between podant peptide chains in a locked conformation, [23][24][25][26] which is thermodynamically stable. [27,28] Work by Hirao et al showed chirality organiza-Abstract: Hierarchical self-assembly of disubstituted ferrocene (Fc)-peptide conjugates that possess Gly-Val-Phe and Gly-Val-Phe-Phe peptide substituents leads to the formation of nanoand micro-sized assemblies. Hydrogenbonding and hydrophobic interactions provide directionality to the assembly patterns.…”

Section: Introductionmentioning

confidence: 99%

“…The introduction of the ferrocene (Fc) group as a part of the peptide scaffold provides control over the secondary structure of the molecular precursor by promoting cross‐strand hydrogen bonding between podant peptide chains in a locked conformation,23–26 which is thermodynamically stable 27. 28 Work by Hirao et al.…”

Section: Introductionmentioning

confidence: 99%

Hierarchical Organization of Ferrocene–Peptides

Beheshti

Martić

Kraatz

2012

Chemistry A European J

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Hierarchical self-assembly of disubstituted ferrocene (Fc)-peptide conjugates that possess Gly-Val-Phe and Gly-Val-Phe-Phe peptide substituents leads to the formation of nano- and micro-sized assemblies. Hydrogen-bonding and hydrophobic interactions provide directionality to the assembly patterns. The self-assembling behavior of these compounds was studied in solution by using (1)H NMR and circular dichroism (CD) spectroscopies. In the solid state, attenuated total reflectance (ATR) FTIR spectroscopy, single-crystal X-ray diffraction (XRD), powder X-ray diffraction (PXRD), and scanning electron microscopy (SEM) methods were used. Spontaneous self-assembly of Fc-peptides through intra- and intermolecular hydrogen-bonding interactions induces supramolecular assemblies, which further associate and give rise to fibers, large fibrous crystals, and twisted ropes. In the case of Fc[CO-Gly-Val-Phe-OMe](2) (1), molecules initially interact to form pleated sheets that undergo association into long fibers that form bundles and rectangular crystalline cuboids. Molecular offsets and defects, such as screw dislocations and solvent effects that occur during crystal growth, induce the formation of helical arrangements, ultimately leading to large twisted ropes. By contrast, the Fc-tetrapeptide conjugate Fc[CO-Gly-Val-Phe-Phe-OMe](2) (2) forms a network of nanofibers at the supramolecular level, presumably due to the additional hydrogen-bonding and hydrophobic interactions that stem from the additional Phe residues.

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Dynamic behaviour of 1,n′-disubstituted ferrocenes

Cited by 17 publications

References 37 publications

Bis- and Trisamides Derived From 1′-Aminoferrocene-1-carboxylic Acid and α-Amino Acids: Synthesis and Conformational Analysis

Bis- and Trisamides Derived From 1′-Aminoferrocene-1-carboxylic Acid and α-Amino Acids: Synthesis and Conformational Analysis

Solid‐Phase Synthesis of Chiral Modular Ferrocene‐Based Peptides

Hierarchical Organization of Ferrocene–Peptides

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