Molecular Design, Supramolecular Assembly, and Excellent Dye Adsorption Capacity of Natural Rigid Dehydroabietic Acid-Tailored Amide Organogelators

Abstract

It is very appealing to synthesize functional soft materials from natural and abundant plant diterpenes because they have conformationally rigid and chiral properties. Herein, dehydroabietic-based monoamide (DA-1) and diamide (DA-2) were designed by introducing device interactions, π-π stacking and hydrogen bonding, with an aromatic group, C═O, and N-H. DA-1 and DA-2 can be gelled in a mixed solvent and a single solvent, respectively. Several novel supramolecular organic gels including highly entangled three-dimensional networks composed of rods or fibers were constructed. Interestingly, DA-2 forms a helical structure that is right-handed under the cooperative control of the solvent and the rigid structure of rosin. Gel formation was primarily driven by hydrogen bonding, π-π stacking, and van der Waals force. Combined with Gaussian calculation and X-ray diffraction (XRD), we established pack patterns for each system, revealing the roles played by rosin and amide groups. Moreover, the carbon tetrachloride gel of DA-2 can effectively remove Congo red in an aqueous solution, and the removal rate can reach 98.4%. This research explores an efficient organic gel for adsorbing Congo red dye with the secretions of pine trees.