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Issue 23, 2016
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Rods, helices and spherulites: diverse self-assembled architectures from l-phenylalanine derivatives

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Abstract

Diphenylalanine (FF) has emerged as a concise self-assembling motif yielding a variety of nanostructures through simple processing. We explored the self-assembly and hydrogelation properties of some L-Phe (F) derivatives having a rotationally flexible and aromatic 1-naphthaleneacetyl moiety as the N-protecting group, while the carboxylic acid residue was converted into an amide by reaction with different amines such as hydrazine (L-NapF-Hz), ethylenediamine (L-NapF-EDA), 3-aminopropylimidazole (L-NapF-API) and hydroxyethylamine (L-NapF-HEA). All the derivatives were dissolved in hot water and the subsequent cooling of these sols had varied outcomes. For some derivatives such as L-NapF-Hz and L-NapF-EDA, molecular self-assembly yielded optically clear supramolecular hydrogels, while for others such as L-NapF-API and L-NapF-HEA, precipitates were obtained upon cooling. Field emission scanning electron microscopy (FESEM) revealed diverse morphologies such as rigid rods, helical nanofibers and spherulites which were obtained by spontaneous self-assembly of these compounds. Circular dichroism spectroscopy revealed π–π stacking as one of the critical intermolecular interactions dictating the self-assembly. Stable hydrogels entrapping the anticancer drug doxorubicin were obtained with L-NapF-EDA only, highlighting the importance of flexibility in the molecule for designing efficient hydrogelators.

Graphical abstract: Rods, helices and spherulites: diverse self-assembled architectures from l-phenylalanine derivatives

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Publication details

The article was received on 24 Dec 2015, accepted on 04 Mar 2016 and first published on 04 Mar 2016


Article type: Paper
DOI: 10.1039/C5CE02545A
CrystEngComm, 2016,18, 4369-4373

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    Rods, helices and spherulites: diverse self-assembled architectures from L-phenylalanine derivatives

    S. D. Bhagat and A. Srivastava, CrystEngComm, 2016, 18, 4369
    DOI: 10.1039/C5CE02545A

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