Issue 37, 2018

Fluorescent supramolecular hydrogels self-assembled from tetraphenylethene (TPE)/single amino acid conjugates

Abstract

Herein, we report the synthesis of simple TPE/single amino acid conjugates, TPE-Ser and TPE-Asp with side-chains featuring functional groups that may provide an additional hydrogen bonding network for hydrogelation in aqueous medium. TPE-Ser, which has the lowest molecular weight, containing hydroxyl groups undergoes self-assembly into supramolecular hydrogels under physiological pH conditions. TPE-Asp with a carboxylic group side chain undergoes the self-assembly and hydrogelation processes under slightly acidic conditions (pH = 6.0). UV-vis, IR, PL and rheological studies clearly indicate the formation, stability and fluorescence properties of TPE-amino acid hydrogels. TEM micrographs of the hydrogels indicate that the compounds are self-assembled into a nanosheet morphology with random size and shape. Further, in vitro analysis of TPE-Ser and TPE-Asp with 3A6 cells shows that the compounds exhibit unique fluorescence signals in microcellular environments thus making them suitable candidates for bioimaging applications. Overall, these findings highlight the importance of the structure-hydrogelation relationship and provide new insights into the design of single amino-acid-based supramolecular hydrogels.

Graphical abstract: Fluorescent supramolecular hydrogels self-assembled from tetraphenylethene (TPE)/single amino acid conjugates

Supplementary files

Article information

Article type
Paper
Submitted
15 3 2018
Accepted
26 5 2018
First published
08 6 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 20922-20927

Fluorescent supramolecular hydrogels self-assembled from tetraphenylethene (TPE)/single amino acid conjugates

N. Chu, R. D. Chakravarthy, N. Shih, Y. Lin, Y. Liu, J. Lin and H. Lin, RSC Adv., 2018, 8, 20922 DOI: 10.1039/C8RA02296H

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