Linker length-dependent morphologies in self-assembled structures of anthracene glucosides

George, A and Jayaraman, N (2023) Linker length-dependent morphologies in self-assembled structures of anthracene glucosides. In: Carbohydrate Research, 533 .

PDF car_res_533_2023.pdf - Published Version Restricted to Registered users only Download (8MB) | Request a copy

Abstract

Anthracenemethyl glucosides, that possess ethylene glycol linkers connecting the glucoside with anthracene moiety, are studied herein. Koenigs-Knorr glycosylation of ethylene glycol-tethered anthracene with acetobromo glucose, followed by removal of the protecting groups, lead to the facile formation of the target glucosides. Aq. solutions of these anthracene glucosides readily undergo self-assembly, with critical aggregation concentration varying between 0.4 and 1 mM, depending on the linker, being ethylene-, di- and tetraethylene glycol, as assessed by photophysical evaluations. Circular dichroism spectra show chiral self-assembled structures for these glucosides in solution, from which a left-handed chirality is adjudged. Morphologies of the self-assembled structures of these glucosides are controlled by the linker length. With the ethylene glycol linker, vesicles form initially, around which tendrils start to grow as the concentration of the glucoside is increased. Whereas, di- and tetraethylene glycol-spaced glucosides prefer agglomerated fractal-like structures, as assessed by microscopies. The aggregation phenomenon in the latter glucosides appears to be under the non-equilibrium-driven, dissipative control. © 2023 Elsevier Ltd

Item Type:	Journal Article
Publication:	Carbohydrate Research
Publisher:	Elsevier Ltd
Additional Information:	The copyright for this article belongs to the Elsevier Ltd.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	04 Nov 2023 06:06
Last Modified:	04 Nov 2023 06:06
URI:	https://eprints.iisc.ac.in/id/eprint/83116

Actions (login required)

View Item