Synthesis and Self-assembly of Novel Nanofeather-like Fluorescent Alkyloxy-Containing Diphenyl Ether Organogelators

Abstract

In this study, novel fluorescent low molecular-weight organogelators are derived from diphenyl ethers and substituted with para-alkoxy groups of different aliphatic chain lengths. The present research promotes the preparation of innovative nanofeather-like assemblies from the synthesized diphenyl ether-derived organogelators. The gelation performance of the prepared alkoxy-substituted diphenyl ethers was reported. The synthesis procedure was achieved by using a base-catalyzed reaction of hydroxyl-substituted diphenyl with various alcohols of different aliphatic chain lengths. The chemical structures of the synthesized diphenyl ether derivatives were studied by 1 H/ 13 C NMR and infrared spectroscopy. Fluorescence and UV–vis absorption spectral analyses showed solvatochromism. The diphenyl ether derivatives with longer alkoxy terminal substituents showed enhanced thermoreversible gelation activity as compared to the diphenyl ether derivatives with shorter alkoxy terminal substituents. The morphological properties of the self-assembled diphenyl ethers were studied by transmission electron microscopy and scanning electron microscopy, which showed supramolecular architectures of highly ordered nanofeathers, enforced by van der Waals interactions and π-stacks. Depending on the length of the aliphatic tail, different morphologies were detected, including nanofeathers, nanofibers, and nanosheets. The antimicrobial and cytotoxic properties of the prepared diphenyl ether-derived organogelators were examined to confirm their possible use in various fields like drug delivery systems.

Differentiating aliphatic and aromatic alcohols using triazine-based supramolecular organogelators: end group-specific selective gelation with chain length of alcohols

“…Ether linkages between the central moiety and the end groups were introduced to increase the flexibility, which in turn enhances the gelation probability by aiding efficient solvent entrapment. 56,57 In this work, the gelation behaviour of each of these three gelators was explored in a range of solvents, including non-polar, polar-protic, and polar-aprotic solvents. The results indicate that cyclohexanol is a better gelating agent for the gelation of all three gelator molecules studied here.…”