The self-assembly of small molecules has attracted increasing interest for the construction of functional soft materials including gels. The generation of stimuli-responsive gels is of particular interest. Ferrocene peptide conjugates have recently received significant attention to make redox (stimuli) responsive supramolecular materials and due to their interesting structural properties.1,2 In this study, the synthesis, characterization, conformational analysis, self-assembly and morphological studies of a series of mono and disubstituted ferrocenyl-tripeptide conjugates have been reported. Herein, we describe how mono and disubstituted ferrocene-peptide conjugates (where the peptide fragment of the conjugate corresponds to the hydrophobic amyloid sequence) self-assemble into smart and responsive organogels by controlling their conformation via proper manipulation of inter-molecular vs intra-molecular hydrogen bonding. Interestingly, the impact of chirality of each amino acid on the conformation, self-assembly and morphology of all ferrocenyl-peptide conjugates has been explored.3 The conformation and self-assembly have been extensively investigated using variable concentration and solvent titration NMR and circular dichroism studies. The morphologies of their self-assembled states have been investigated by transmission electron microscope which showed the significant effect of chirality on the resulted morphologies of the aggregates. The redox responsive properties are also explored to make redox controlled and reversible supramolecular transformation between gel fibers and micelles. This study will help to design next generation redox-responsive supramolecular systems on ferrocene-peptide conjugates based on their conformation and hydrogen bonding capabilities. References: 1. Adhikari, B.; Afrasiabi, R.; Kraatz, H.-B. Organometallics, 2013, 32, 5899–5905. 2. Adhikari, B.; Kraatz, H.-B. Chem. Commun. 2014, 50, 5551–5553; and references therein. 3. Unpublished work.

Impact of H-bonding and chirality on the self-assembly (and morphology) of mono and disubstituted ferrocenyl-peptideconjugates

249th National Meeting (2015)

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