Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates

Natural and abundant plant triterpenoids are attractive starting materials for the synthesis of conformationally rigid chiral building blocks functional soft materials. Here, we report rational design three oleanolic acid–triazole–spermine conjugates, containing either one or two spermine units in target molecules, using Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The resulting amphiphile-like molecules 2 3, bearing just unit respective self-assemble into highly entangled fibrous networks leading to gelation at a concentration as low 0.5% alcoholic solvents. Using step-strain rheological measurements, show rapid self-recovery (up 96% initial storage modulus) sol ? gel transition under several cycles. Interestingly, flow curves reveal thixotropic behavior gels. To best our knowledge, this kind was not shown literature before, neither triterpenoid nor its derivatives. Conjugate 4, having bolaamphiphile-like structure, found be nongelator. Our results indicate that position number alter properties, strength, their self-assembly behavior. Preliminary cytotoxicity studies compounds 2–4 four human cancer cell lines suggest affect biological activity. also encourage exploring other derivatives sustainable, renewable, biologically active multifunctional organic nanomaterials.