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Linker length-dependent morphologies in self-assembled structures of anthracene glucosides
Anne George1, Narayanaswamy Jayaraman1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India.
Carbohydrate Research
|September 8, 2023
Summary
Anthracenemethyl glucosides self-assemble in aqueous solutions, forming chiral structures. The linker length controls the morphology of these self-assembled anthracene glucoside structures.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Anthracene derivatives are known for their photophysical properties.
- Self-assembly is a key phenomenon in creating ordered structures from molecular building blocks.
- Glycosides offer tunable solubility and biocompatibility.
Purpose of the Study:
- To synthesize novel anthracenemethyl glucosides with varying ethylene glycol linkers.
- To investigate the self-assembly behavior of these glucosides in aqueous solutions.
- To elucidate the influence of linker length on the self-assembled structures' morphology and chirality.
Main Methods:
- Koenigs-Knorr glycosylation for synthesis of anthracene glucosides.
- Photophysical evaluations to determine critical aggregation concentration (CAC).
- Circular dichroism spectroscopy to assess chirality.
- Microscopy techniques to analyze self-assembled morphologies.
Main Results:
- Facile synthesis of target anthracene glucosides achieved.
- Self-assembly observed with CACs between 0.4 and 1 mM, dependent on linker length.
- Chiral, left-handed self-assembled structures were identified in solution.
- Morphology varied with linker length: vesicles with tendrils (ethylene glycol) vs. fractal-like agglomerates (di- and tetraethylene glycol).
Conclusions:
- Anthracenemethyl glucosides are capable of forming ordered, chiral self-assembled structures.
- Linker length is a critical parameter in controlling the morphology of self-assembled anthracene glucosides.
- The aggregation of longer-linker glucosides suggests non-equilibrium, dissipative control.
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