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All Journal Jurnal Penelitian Saintek
Herayati
Institut Teknologi Sumatera
Decision Sciences, Operations Research & Management

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Synthesis, characterization, and micellar behavior of amphiphilic chitosan bearing sulfate and anisaldehyde imine groups Herayati
Jurnal Penelitian Saintek Vol 31, No 1 (2026)
Publisher : Universitas Negeri Yogyakarta

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.21831/jps.v30i1.89435

Abstract

Amphiphilic chitosan derivatives bearing sulfate and anisaldehyde imine (anisimine) groups were successfully synthesized and characterized for potential applications as functional biomaterials. The synthesis involved two key steps: (1) sulfation of chitosan using chlorosulfonic acid to introduce O-sulfate groups, and (2) Schiff base formation via reaction with p-anisaldehyde to generate N-anisimine functionalities. Structural modifications were confirmed by Fourier-transform infrared (FTIR) spectroscopy, which showed characteristic absorption bands at ~1250 cm⁻¹ and ~820 cm⁻¹ corresponding to O=S=O stretching of sulfate, and a C=N stretch at ~1640 cm⁻¹ indicating imine formation. Proton nuclear magnetic resonance (1H-NMR) spectra further verified the successful attachment of aromatic protons from p-anisaldehyde and the disappearance of primary amine peaks, confirming imination. The amphiphilic behavior and micelle-forming ability of the N-anisimine-O-sulfated (NAOS) chitosan were evaluated using pyrene as a hydrophobic fluorescent probe for determining the critical micelle concentration (CMC), which was found to be 0.012 mg/mL. The observed low CMC value indicates strong self-assembly capability in aqueous media. These results suggest that NAOS chitosan possesses promising structural and surface-active properties suitable for advanced applications in drug delivery and cosmetic formulations.
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