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Issue 29, 2019
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Highly selective metallogel from 4-biphenylcarboxy capped diphenylalanine and FeCl3

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Abstract

The gelation property of the iron(III) complex of 4-biphenylcarboxy capped diphenylalanine (L-Phe–L-Phe, the hydrophobic core motif of Alzheimer's β-amyloid polypeptide) has been reported. Gelation was observed selectively for FeCl3 and 4-biphenylcarboxy capped diphenylalanine, whereas Cd, Cu, Zn, Cr, Ni, Hg, Mg, Mn, Pb, and Pd complexes were not able to form a metallogel. However, Boc and acetyl capped diphenylalanine have failed to form a metallogel. The storage modulus of the metallogel was approximately an order of magnitude larger than the loss modulus, which indicates the elastic nature of the gel and the physical crosslink. The metallogel exhibits an entangled fiber network which is stabilized by weak interactions such as coordination, hydrogen bonding and π–π interactions. The solid-state study shows that the acetyl protected diphenylalanine adopts an extended conformation and forms a supramolecular helix-like structure through multiple intermolecular hydrogen bonds. However, the 4-biphenylcarboxy protected diphenylalanine shows a supramolecular sheet-like structure through intermolecular hydrogen bonds and π–π stacking interactions between the biphenyl moieties.

Graphical abstract: Highly selective metallogel from 4-biphenylcarboxy capped diphenylalanine and FeCl3

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Publication details

The article was received on 06 May 2019, accepted on 30 May 2019 and first published on 12 Jun 2019


Article type: Paper
DOI: 10.1039/C9CE00695H
CrystEngComm, 2019,21, 4289-4297

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    Highly selective metallogel from 4-biphenylcarboxy capped diphenylalanine and FeCl3

    S. Sasmal, K. Maji, D. Díaz Díaz and D. Haldar, CrystEngComm, 2019, 21, 4289
    DOI: 10.1039/C9CE00695H

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