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Supramolecular hydrogels with chiral nanofibril structures formed from β-cyclodextrin and a rosin-based amino acid surfactant.

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Rational combination of natural molecules is expected to provide new soft material building blocks. Herein, a rosin-based amino acid surfactant was synthesized using dehydroabietic acid and L-serine as the starting… Click to show full abstract

Rational combination of natural molecules is expected to provide new soft material building blocks. Herein, a rosin-based amino acid surfactant was synthesized using dehydroabietic acid and L-serine as the starting materials (denoted R-6-Ser). Supramolecular hydrogels were formed when β-cyclodextrin (β-CD) was mixed with R-6-Ser at molar ratios of over 0.5:1 and above certain concentrations. The hydrogels were investigated using rheometry, small-angle X-ray scattering, CD spectroscopy and cryo-transmission electron microscopy (cryo-TEM). The β-CD associated with the isopropyl benzyl group of the dehydroabietic acid unit in R-6-Ser and formed R-6-Ser@β-CD complexes. The complexes and R-6-Ser self-assembled to form elongated right-handed rigid fibers with a diameter of approximately 7-8 nm, which were responsible for the elasticity of the hydrogels. This work demonstrated the feasibility of preparing supramolecular hydrogels from a diterpenoid-based surfactant and β-CD and provides a new means of utilizing the secretions of pine trees.

Keywords: supramolecular hydrogels; acid surfactant; amino acid; rosin based; acid; based amino

Journal Title: Journal of agricultural and food chemistry
Year Published: 2020

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