Issue 23, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Dec 2015
Accepted
04 Mar 2016
First published
04 Mar 2016

CrystEngComm, 2016,18, 4369-4373

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements